Stevie Case is the Chief Revenue Officer at Vanta, the $4B leader in trust management and compliance automation. Since joining in 2021, Stevie has scaled the company from sub-$20M ARR to north of $100M, navigated 40+ copycat competitors, rebuilt both pre- and post-sales engines, and led Vanta’s expansion from SMB into enterprise. A former world’s first female pro gamer turned tech sales leader, Stevie previously held senior roles at Twilio, where she helped grow the enterprise business to a $1B run rate.
Discussed in This Episode
- How Stevie’s path from pro gamer to CRO shaped her competitive edge
- Early-stage chaos at Vanta and the signs of undeniable product-market fit
- Battling over 40 copycat competitors with value selling and a “CIA” competitive squad
- Why execution, not first-mover advantage, is the only sustainable moat
- The challenges and lessons from scaling SMB sales and moving into enterprise
- Building go-to-market experiments before committing product investment
- Transforming post-sales into a growth engine and driving net retention up
- Stevie’s view on AI in revenue operations and personal productivity
Episode Highlights
00:00 — “Every business is subject to the laws of physics and math… Execution is the only moat.”
03:07 — Stevie on becoming the world’s first female pro gamer and how competitiveness fueled her career.
06:25 — The undeniable product-market fit that convinced Stevie to join Vanta.
14:02 — Facing 40+ copycat competitors and learning that flashy marketing can’t beat sustainable growth.
16:23 — Transitioning from transactional selling to deep, value-based discovery using MEDDPICC.
18:30 — Creating Vanta’s “CIA” Competitive Intelligence Agency to win back customers.
26:10 — Launching the experimental enterprise sales team and the patience it took to scale it.
47:08 — Rebuilding post-sales into separate customer success and account management functions.
50:56 — Vanta’s next big GTM bets: platform sales, public sector, and deeper enterprise expansion.
53:27 — How Stevie is using AI in revenue operations and her own work life.
Guest Links
LinkedIn: https://www.linkedin.com/in/steviecase
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Transcript
Episode Transcript
Available transcripts are automatically generated. Complete accuracy is not guaranteed.
Stevie Case (00:00):
Every business is subject to the laws of physics
and math.
It looks magical from theoutside.
Every one of those businesseson the inside felt like chaos.
We had 40 plus copycatcompetitors.
It was wild.
Execution is the only mode.
Nobody cares if you were first.
Sophie Buonassisi (00:39):
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(01:22):
Today on the podcast, stevieCase, cro of Vanta.
Vanta just raised a $150million Series D and is now
valued at over $4 billion.
Stevie took the company fromSMB to enterprise, battled over
40 copycats, rebuilt both preand post sales engines and
continues to lead revenue at theunicorn.
In this episode you'll learnearly growth decisions, her
(01:43):
first hires, her systems, whatshe deep prioritized, how she
tested and scaled to enterprise,how Vanta beat over 40 copycats
with pricing strategy, valueselling and a CIA competitive
squad.
How they drive expansion andwhy execution is the only moat.
We're proud to be an earlybeliever in and backer of Vanta
(02:03):
as an investor.
All right, let's get into it.
Stevie, welcome to the podcast.
Thank you, so excited to behere, so excited to have you,
and I mean what perfect timingwith all the momentum that
Vanta's experienced.
Huge congrats to you on theraise.
Stevie Case (02:18):
Thank you.
I feel really lucky.
We're still having a lot of fun.
Sophie Buonassisi (02:22):
That's the goal right.
You can scale and have fun atthe same time.
That's when you know that'sright Incredible.
Well, take us back a little bit.
You know, maybe even before youjoined Vanta, you've got an
interesting background.
Love to unpack that a littlebit and how that led you to
Vanta.
Stevie Case (02:41):
Yeah, I've got a very non-traditional start to my
background.
So I started at well.
I started out in collegethinking I was going to be a
lawyer and I was pre-lawpoli-sci doing that path and I
kind of fell in love with videogames and ended up becoming the
world's first female pro gamerworld's first female pro gamer.
(03:07):
And that was a long story, longseries of events, but there are
some common threads and thatearly beginning as a competitive
gamer really put me on thispath towards making games, which
games are really just softwareat the end of the day.
So then I was a product managerand ultimately ended up getting
offered an opportunity tobecome a salesperson.
Ultimately I ended up gettingoffered an opportunity to become
(03:27):
a salesperson, learned how todo that and over time my
portfolio started out as 100%video game companies and became
more and more mainstream tech.
And years later here I am and Ithink honestly I look back and
it seems a little crazy likeit's a path that doesn't make a
lot of sense on paper, but thereare absolutely common threads.
Path that doesn't make a lot ofsense on paper, but there are
absolutely common threads and myintense competitiveness is
(03:48):
probably the single unifyingthread from start to finish.
Sophie Buonassisi (03:53):
I love it.
I always think we think aboutcareers too linearly in a way,
so there's always a commonthread.
It's more of an ecosystem thanone linear path.
Stevie Case (04:03):
Absolutely.
I'm a big fan of really leaninginto things that are
uncomfortable and I love tochallenge myself and love to
grow.
And you know, if I had set outand designed a career early on
that was only made of thingsthat I knew about at the time, I
wouldn't have gone very far.
(04:23):
You know, I grew up in KansasCity, kind of outside of Kansas
City, in the country.
I had no exposure to business,I had no exposure to a lot of
things, and so I've been reallylucky to get these opportunities
where I've been able to expandthe universe of what I am, what
I even know about and what I getto be in the room to talk about
(04:43):
.
And so I've done that.
I try to find those littleedges that are a little more
unknown or maybe a little moreuncomfortable, and I tend to
embrace those and sort of diveright in.
Sophie Buonassisi (04:55):
Incredible and you go from smaller towns
pro gamer product manager toVanta.
What was Vanta's revenue andgo-to-market setup when you
joined?
Stevie Case (05:06):
Yeah, we were much smaller so Vanta.
Today you know we're north of athousand people.
When I started we were lessthan 200 people.
We were single double digits ofmillions in revenue, digits of
millions in revenue.
So like pretty early on thejourney when I joined I just
(05:31):
started with North Americansales only.
So when I joined on day one Ihad about 20 people on my team,
mostly sales people, and it wasvery early days.
There was a ton of excitement.
It was super clear.
There was this very intenseproduct market fit, but from a
go to market perspective, not alot of structure.
(05:53):
It was 100% inbound, not usingCRM in a meaningful way, no
forecast cadence, like you knowit was.
The vibes were high but thestructure was not really
existing yet.
So I kind of liked that.
It was a.
It felt like the Wild West ofit at that time.
Sophie Buonassisi (06:12):
Hey, better than the opposite.
Right, that's right, that'swrong.
The vibes are high.
All the structure can bebrought into place.
Yeah, what made you believethat it could scale to be an
$100 million plus company?
Stevie Case (06:25):
Yeah, you know I really I struggled with that
question because I think it'seasy to look back and say, oh, I
saw this thing and it was soobvious.
I don't think that's often true.
And there were some things atthat point with Vanta that made
it clear that the long termpotential for the company was
(06:47):
massive and the biggest of thosewas, honestly, just the product
market fit was off the chartsand you know people debate what
that means or like how do youknow you've got product market
fit?
What I can tell you is peoplewere coming inbound at a wild
clip and when we would get onthe phone with founders we were
(07:11):
seeing one call closes.
We were seeing just these likeoh my gosh, please give it to me
now, because you are solving apain that is so intense and so
significant.
And at that time our first usecase was helping founders get
SOC 2 compliant for the firsttime.
And so they were coming to usand saying I have a customer
(07:32):
deal and it's requiring thiscustomer's requiring that I have
a SOC 2 audit complete and thatI can give them the report to
get the deal done.
So it was revenue blocking andI really liked that because you
know people only really buy forthree reasons.
Right, it's either going togrow revenue, it's going to
reduce costs or it's going toreduce risk.
(07:53):
At the end of the day, thoseare the only three reasons
people buy things and of those,growing revenue is a much more
compelling reason to buy thansome of the other reasons.
So to have that as our primarymotivator was huge.
And so to see there's this likereally intense pain.
It's a revenue blocker.
There's a lot of inboundinterest and in that process of
(08:16):
getting to know the company, oneof the things I did was one of
the salespeople gave me a demo,so I got an AE to give me a demo
.
Salespeople gave me a demo, soI got an AE to give me a demo.
And you know it was fascinatingbecause it was, in some senses,
the demo was super simple.
The sales process was supersimple.
There was nothing.
There were no, there was nolike over the top sales magic to
(08:37):
drive these deals to close.
It was like that compelling ofa product.
So for me, that was the likeokay of a product.
So for me that was the likeokay, this is very real and we
can clearly sell more of this.
There's a lot of demand.
The thing that I questioned andthis came later was sort of
like where does it go from there?
And that became the bigquestion of the next era.
Sophie Buonassisi (09:02):
And was there a moment early on when you had
that question in your mind,where you thought you might have
made the wrong call?
Stevie Case (09:11):
You know I don't know that I ever felt like I
made the wrong call, but therewere some times that were very,
very hard.
You know, even in the beginning, as I was debating joining, you
know I talked to Andrew Reidfrom Sequoia, who's on the board
Vanta, and you know I wasasking him sort of like where
does this go from here?
(09:32):
Like this is obviously great,we've got good product market
fit, founders love us, but we'reselling to very small companies
and we're selling very smalldeals.
And you know I'll never forgethim saying this was like a
Sunday night, as I was trying tolike make this decision Sunday
night at like 11pm or something,and I'm on zoom with Andrew and
(09:53):
I'm like it's a great wedge,but like to what?
And he said I don't know, butit's a hell of a wedge and like
there was like something in that.
And you know, like therecognition, I was like okay, I
actually can roll with that.
Like I am totally good withambiguity, I can, I am a big
(10:13):
believer, I love to bet onmyself and I think Christina,
the founder of this company, isbrilliant, like I want to bet on
her.
So the bet was we've gotsomething really great and a lot
of product market fit.
We're going to figure it out.
And that became like my first 18months.
So there was a lot of work.
We had a lot of copycatcompetitors.
We had like a whole thing to doin that first 18 months and
(10:37):
then we also had to figure outwhere we were going as a company
in the future.
And you know, in that first 18months there there were some
extremely hard times.
You know, we were in a revenuerut for a long time where three
or four quarters in a rowrevenue didn't really grow.
And when you join as the chiefrevenue officer and you can't
(10:58):
grow revenue, it's not good.
So I wouldn't say I thought Imade the wrong choice.
Necessarily I thought maybethey made the wrong choice.
I was definitely.
Yeah, I mean, at the time,though, I was like I don't, I
can't, I can't crack the code,like I'm showing up every day
trying to figure out how to makerevenue go up and to the right,
(11:21):
and like I cannot crack thecode and I'm like trying
everything I can think of.
So you know, we did it.
After about 12 months, thingsstarted to inch up into the
right and then, about 18 monthsin, it was like okay, okay, we
figured this out.
We figured it out.
I figured out how to getrevenue to go up into the right,
(11:42):
but, man, it was not easy.
It was not easy.
Sophie Buonassisi (11:47):
And I feel like those are the common
sentiments you hear from anyonein the early days.
It's easy to see VantageousSeries D now and think, wow,
that's incredible.
But there were people in thetrenches yourself and others,
christina and everyone just justyou know working day in and day
out to make it go up into theright, so really it's a
testament to that.
Stevie Case (12:06):
I mean, I think that that's for me, the biggest
lesson, because you look back onthis and it's like, okay, it's
an obvious success and I justdon't know that.
That is true pretty muchanywhere.
You know, you look at all thesecompanies Figma IPO'd this week
and you listen to what theywent through and incredible
(12:28):
product, but it wasn't linear.
You know, it was hard and thatwas of those first 18 months.
I think the biggest lesson init was every business is subject
to the laws of physics and mathand while it looks magical from
the outside and like there'sfairy dust and it's just
(12:49):
happening, and like revenueshowed up and the growth was off
the charts, it is so true that,like every one of those
businesses on the inside feltlike chaos, had to grind so hard
, hit so many obstacles wherethey couldn't figure it out or
it didn't make sense.
And the proof point that I liketo take for that with Vanta is
(13:11):
that we had, at one point, 40plus copycat competitors.
Wow, it was wild and this isone of the reasons I was brought
in as CRO is we had, you know,vanta was the first to market.
Christina created this marketand this concept of the product
brought it to market first.
(13:32):
We then had several companiessee the product market fit and
go, oh, we can build that.
So they, you know, in somecases went off and like, built
an offshore copy and like athird party dev shop and and
then came with flashy marketingand we're like, oh, we're Vanta,
just half the cost.
And we went through this entirephase where, you know, it felt
(13:55):
to us and, I think, to some inthe market, like some of those
copycat competitors were winning.
And what I learned through thatprocess?
I learned a lot through thatprocess, but one of the biggest
things I learned is that you canfool people with marketing for
a little bit and you can usethat as a cover to create a ton
of momentum.
But every business is stillsubject to those same rules, the
(14:18):
same math.
You're still.
You still got to figure out howto get your net retention to be
positive.
And on the up and up, you stillgot to figure out how to get
your net retention to bepositive.
And on the up and up, you stillgot to figure out how to drive
real sustainable growth.
You still have to build ago-to-market engine.
And you know, flashy marketingand software built cheaply
offshore, it doesn't really getyou there.
(14:41):
So you know I'm grateful forthe lesson.
It doesn't really get you there, so you know it was a I'm
grateful for the lesson.
We you know we we have pulledaway from the pack and that has
been incredibly gratifying butwas not easy.
Sophie Buonassisi (14:52):
Incredible, I think I mean more than ever.
Now.
There's copycats popping up andit's a common challenge for
other companies, for otherfounders, for early stage
go-to-market leaders, for othercompanies, for other founders,
for early stage go-to-marketleaders.
How would you advise othersagainst that?
You know you've combated 40plus other copycats.
Stevie Case (15:18):
How do you win?
Yeah, well, I mean, I am a bigbeliever that execution is the
only mode.
So you know, nobody cares ifyou were first, nobody cares if
you originated the market or youknow that you've been in it
longer.
They just want to know that youare going to give them the most
value and that they are goingto be well taken care of and,
ultimately, that you've got thebest experience that's going to
help them achieve their goals.
Like that is all customers careabout.
(15:39):
So my advice to folks who getinto this situation because it
is so common now you'll seethere's a successful business
Immediately.
People go out and buildcopycats and sometimes that
number two ends up winning, andthere are some key things you
can do in there to head it off.
So you know that focus onexecution at the heart.
The things you got to do.
One is put your head down andstart going faster.
(16:03):
You know, use it as anopportunity to say, okay,
there's something here we needto now speed up and up our game.
So you got to really gettighter on your execution.
A couple of the key tacticalthings that I think really make
a difference.
One is you really have to focuson value.
This was the big transition thatwe made as a go-to-market
(16:26):
organization in my first 18months is we went from a inbound
transactional sale.
We used to say it was kind oflike do you need a pen?
I have a pen.
It was very, very sort of weknow what we have is valuable.
You need the thing?
Here's the thing.
Discovery-wise, we were doing asimple version of Bant.
(16:47):
It was just like super, youknow Bant, here's the demo.
Great, here's the order form.
We had to move from that to areally different value based
sale with much deeper discovery.
So we had to get really curiousabout why our customers were
buying and why they wereinterested in us, what the pain
was.
So train the team on MedPickand really started to enforce
(17:10):
that and like dive deep into theart of discovery, which is
something I'm super passionateabout.
It's like anytime I work withfounders or anybody trying to
build a sales team, my numberone piece of advice is like
learn how to do great discovery.
If you do that like, it's hardto go wrong.
Everything else is kind ofextra.
But if you do great discoveryand you're super curious and you
ask those second and thirdlevel questions, you're you're
(17:33):
going to be on a great path.
So that's one.
Two, then, was to quantify thevalue of our platform.
So it wasn't just here's thesoftware, here's the features
and functions.
Do you want to buy it?
It was, okay, let's understandthe pain in your business.
What are you trying to solve?
Okay, this is blocking a deal.
What's the deal worth?
When do you need to get thedeal done?
(17:54):
What are the resources you haveto take this project on?
Let's start to quantify that.
And then we were able to tell astory of the revenue that we
could unblock, of the resourcingwe could save, the time we
could save, and we were able tothen compare to those cheaper
competitors in a very favorableway, even though we are a
premium solution.
We were able to prove it withmath that we were delivering
(18:18):
more value for every dollar.
That focus on value is at theheart of it.
And then, from there, there'slike a lot of little tactical
things we did beyond that valuetransformation.
Things like we created acompetitive takeout squad and
they weren't on quotas, theywere just on a takeout target.
So they became our experts onthese competitors and they
(18:40):
learned them inside and out andthey just developed the perfect
talk tracks called them the CIA,the Competitive Intelligence
Agency, and this squad of folks.
They were doing their own deal,so they were going trying to
like, rip customer logos andthey'd go down all the logos on
the competitor's website and tryto take them away.
They would also get on callswith the rest of the sales team
(19:02):
and be that voice of like here'show you win and here's what we
know and here's why we knowwe're a better solution for you.
So there was just a lot oftactics in there and at the end
of the day, it was all aboutbuilding confidence that what we
were saying was true we havethe better solution, we can
deliver more value and we'regoing to give you a better
experience.
Sophie Buonassisi (19:26):
And that was one of the challenges that you
faced in your first 18 monthsthe 40 plus copycats.
Take us back to the beginningNow.
What was the state of revenue?
And then you mentioned thego-to-market engine.
Where it was.
What were your first moves froma go-to-market standpoint to
actually scale?
Stevie Case (19:41):
Yeah, I mean, in those early days the state of
revenue, honestly, was unclear.
One of the biggest challenges Ihad at the very beginning is
that we had no measurement, andthis is actually one of the
biggest mistakes I look back at,because I came I came from
(20:03):
Twilio where I was mentored byour CFO, george Hu, who at his
core, is really an analyst likeso deeply, deeply math driven I.
That is how I lead a team aswell.
It's very math driven.
But when I arrived at Vanta, wedidn't have the.
We didn't have any analyticsinfrastructure, there was no
measurement.
I could not see anything andwhile I pushed to build that
(20:29):
function and that team, I kindof accepted the no.
When I got the no and I wastold oh, we've got a product
analytics team, use what they'vegot, it's fine.
I accepted that and that isprobably the single biggest
mistake I made when I look backon it, because it meant I went
about a year without reallybeing able to see what was going
(20:52):
on in my business and it led meto make some incorrect
decisions along the way, becauseon arrival, you know, one of
the first pieces of advice I gotwas you need to hire like
there's a ton of demand.
We're not serving that demandadequately.
Like hire people.
So I went out and I hired abunch of SMB sellers, like very
(21:12):
junior SMB sellers, because atthe time the business looked
like a very down market business.
And you know, the thought atthe time was we can hire junior
sellers at you know a fairly lowcost and they can still be
effective because our win ratesare off the charts.
But I couldn't.
I couldn't measure anything.
So I was going on instinct andadvice and what we found was we
(21:33):
brought those people in and won.
The competitive landscapeshifted and our win rates went
down and we found that the salewas actually more complex than
it appeared to be from theoutside and one of the things
under the covers was that thecustomer base of prospects were
a little more complicated thanwe thought.
(21:53):
It wasn't just sort of downmarket tiny startups and
founders.
There was like enterprise mixedin there.
There was like some interestingkind of blend.
There was like enterprise mixedin there.
There was like some interestingkind of blend.
And so these SMB like firsttime sellers were struggling.
So for the first time we hadfolks come on and like miss
(22:13):
quota, and that was rough.
So, going back to that, it waslike that was my first mission
was hire.
And then I hired and it didn'twork.
And not only did it not work,we had people join that didn't
hit quota.
It obviously diluted theinbound lead flow.
So then you've got people thathave been here a long time who
were like kind of with not a tonof effort, doing like 300% of
(22:34):
quota, who are now like maybesort of making number and maybe
not consistently and, as you canimagine, that like crushes the
spirit of a sales team For sure.
So it was like this very toughmoment and there were a lot of
lessons in there.
For me, number one was nevercompromise on your measurements,
like you have to be able to seewhat's going on before you make
(22:55):
real decisions, otherwise youare bound to fail because you're
going to make assumptions andyou're going to get it wrong.
Number two was really likeconfidence in a sales team
matters more than a lot of otherthings and keeping morale high
and confidence high isfundamental to a winning culture
.
So lots of lessons learned inthere.
(23:16):
But you know we recalibratedand changed the plan.
Sophie Buonassisi (23:22):
And where did you pivot from there?
What were the most defininggo-to-market shifts after that
point?
Stevie Case (23:28):
Yeah, the next big one was we had to really
recalibrate.
At that point as a business.
A couple of things had becomeclear.
One was I had gotten the talentprofile wrong, so we had hired
the wrong kind of folks, and tome that is one of the worst
mistakes you can make, becausethese are people's careers and
(23:52):
you've just hired them into ajob that they're probably not
set up to succeed at.
So, like on a human level, thatwas kind of devastating.
So we had to recalibrate onthat.
We knew we had to up level thetalent.
The second thing we learnedthrough that is, you know, I did
not own marketing at that timeand we had sort of made this
(24:13):
growth plan together and we weregoing to double the size of the
sales team and marketing hadagreed to, you know, double the
inbound pipeline, because atthat time marketing was
responsible for 85% of thepipeline.
Well, not only did I get thehiring profile wrong, marketing
was not able to double pipeline.
So we hired all these folkswrong profile and then we did
(24:35):
not feed them and we did nothave the wherewithal to really
drive outbound at scale yet.
So we ended up in this positionwhere we had a team that wasn't
getting enough inbound, wasn'treally able to close as much of
what they were getting as theycould before.
And then, you know, we had tomake some tough decisions.
(24:57):
So we scaled down the size ofthe team a bit recalibrated,
started to build in moremeasurements, we up-leveled in
marketing and we decided to sortof give it a second go, but in
a much more math-based way.
So this time we, you know,locked hands and had an
(25:21):
agreement that was math-basedand we started to go forward
with a little bit more seniortalent.
We went a little more slowly andwe started to, instead of like
just making big bets and likehiring a bunch of people to go
do something, we started to geta little more incremental.
So in go to market, for example, you know, we started hiring a
(25:42):
slightly different profile ofperson.
We just hiring a slightlydifferent profile of person, we
just hired a few, we saw howthat went and then we would
incrementally add a little bitmore.
So it was a much more measuredapproach.
We also took that realizationthat there was a little bit of
enterprise and mid-market in ourpipeline and what I wanted to
(26:04):
do was start to go after that ina meaningful way.
So we broke out a team for thefirst time.
We segmented.
Basically we had just had asales team.
There was no segmentationbefore, so segmented, built a
team that was specificallytasked with working the sort of
like lower mid-market to smallenterprise leads.
Started small with that, butthat was the first time we
(26:27):
really broke into two teams, twosegments, and then we started
to think about that opportunitya little differently.
That muscle obviously isextremely different.
The sales cycle looks very,very different than the down
market one, so we wanted tocreate the space for them to go
after that.
So that was one of the next biginflection points was that
split of like okay, this isn'tjust a business that sells to
(26:48):
startups, we're going toactually go after something
different at the same time.
Sophie Buonassisi (26:52):
And it sounds like the signal for that was
you had inbound in your mix andwhen you created this team, was
it experimental?
Were you fairly confident thatthis would work and be your
wedge to go up market?
Stevie Case (27:05):
It was experimental .
It was experimental and youknow, the thing that I saw was
there was enough inbound frommid-market and enterprise in the
pipeline that I knew there wassomething there, but I, like I
did not know enough about whatthat thing was Like.
We knew the use case downmarket was this you know, first
(27:26):
time compliance for founders andwe had then expanded the
platform and we had added otherframeworks so we were supporting
things like ISO and HIPAA andGDPR.
So we were kind of expandingwith founders as we went up
market.
We just did not know.
We did not know what was thereand there was a whole space up
there, it turns out, calledgovernance, risk and compliance
(27:49):
where these so we were startingto there compete against a
totally different cohort ofcompanies.
So legacy platforms like Archerand One, trust and Diligent and
(28:16):
MetricStream these companiesthat, like frankly, I'd never
heard of and we started to seethem in deals and it was a tiny
team to start.
It was very much an experiment.
I set the expectation that,like this is going to take time
to work and we need to do theright thing by the team, which
means, like giving them a littlemore ramp, giving them a little
(28:37):
bit more buffer running, morespiffs, like giving them more
space to learn, because we don'tknow what we don't know.
But they did.
They started to build a littlemomentum and you know our
original head of sales, he tookthis on as a project to help us
build this upmarket team and,like that small team started
hitting numbers.
So we started growing it and,you know, just started trying to
(29:00):
kind of learn and like tryingto learn even the vocabulary of
that upmarket buyer, which wasextremely different from that of
the founders we had beenselling to.
Sophie Buonassisi (29:10):
Because it was experimental and that's
great that you got traction.
But how did you forecast that?
Stevie Case (29:16):
Yeah, you kind of can't Fair enough.
That in and of itself wassomething we had to get
comfortable with and this hascarried through the journey.
So when it started as anexperiment, you know, one of the
agreements at our leadershipteam level was this is an
experiment and the same mathcan't apply.
(29:39):
It's not fair to take AEs whoare going into a segment we've
never sold into, we don't evenreally understand what the
market looks like, we don't knowthe dynamics, we don't know
what the sales cycle is going tobe, and then hold them to some
artificial standards.
We did put them on quotas, butthen we really tried to do right
by them.
Frankly, we didn't, at the topline, count on the revenue.
(30:02):
We just, you know it was extra,it was bonus and we have
continued to build that way.
You know, the second year wedid that it's like okay, there's
something here.
Then we built it into more of atrue enterprise team.
But you know, in a normal salesorg you're going to forecast
that that team is going toattain a healthy amount of the
(30:23):
rolled up quota.
You know, 70%, 80% depends onthe segment.
With this enterprise team, youknow we started out the first
year and we said, we are onlygoing to count on them hitting
50% because we just don't knowwhat we don't know.
So we'll apply some math andwe'll test against it, but we're
going to set expectations lowand then we're going to work to
take care of our people alongthe way and make sure they all
(30:44):
are getting, you know, takencare of for helping us figure
out this new segment.
But as a business we can'tforecast it.
You have to get comfortablewith that and I think this is
one of the biggest mistakes thatpeople make.
When they enter a new segment,or even, honestly, when founders
make a first sales hire, theyfeel like, oh, I have to put
this person on a quota and itneeds to be an industry standard
(31:06):
quota, and if they don't hitthat fairly quickly, things are
wrong.
It's a huge mistake because youjust don't know what the right
math is and if you don't createthe space to figure it out,
you're going to be doomed tofailure.
You know I work with a lot ofsmall companies.
(31:27):
Worked with one recently andthey told me a story I've heard
a million times, which is theyhad an early sales team.
They were paying that salesteam a lot of money, and this is
true often when businessesstart they're like, oh my gosh,
salespeople make a lot of moneyand it makes them uncomfortable,
like these salespeople aremaking a lot of money, they're
not hitting their target.
So what this founder did was hefired that sales team and he
(31:51):
hired a way more junior, cheapersales team and then put them
against a quota and he said,looking back, he's like that was
probably a mistake.
Yes, that was a mistake.
Just because you've gotexpensive salespeople and
they're not quite hitting quota,that doesn't necessarily mean
your solution should be getcheaper salespeople.
You've got to figure out how togive them the space to get to
(32:13):
productivity and in the case ofmoving up market, that could
take years.
That might not be a one quarteror two quarter thing, that
might be a two or three yearthing.
So you got to have the patience.
Sophie Buonassisi (32:25):
Great advice overall, with the patience and
what time frame were you whenyou started this upmarket
experiment?
What year are we looking?
Stevie Case (32:34):
at.
This was like six months intomy tenure, so we're looking at
like mid 2022.
Like this is early, early in mytenure at Vanta.
So we're now three years in tothat journey.
Sophie Buonassisi (32:47):
How long did it take for you to gain true
enterprise traction from thatexperiment mid-2022?
Stevie Case (32:54):
From that point to get real enterprise traction two
years, maybe even a little more.
You know we had wins Not to saywe didn't have wins but there's
a difference between gettingthese sporadic kind of lumpy
wins and getting to somethingthat can actually scale.
(33:17):
And we hit that point where Ifelt like this team has scalable
success towards the end of lastyear.
And that's the point at whichit's like OK, we believe that we
can hire new reps and know howlong it's going to take them to
ramp and be relatively confidentthat we can give them enough
(33:39):
pipeline and that they can hit areasonable percentage of their
quota.
And if you can do that and youcan put more reps on the team
and you can repeat that playbook, then you know you've got
something that can scale.
And that does often take yearsand it did.
It took two, two and a halfyears for us.
(33:59):
And now that we're there, it'sphenomenal and they will be, you
know, a huge percentage of nextyear's target.
You know there are a materialpercentage of this year's target
.
So we do count on them now toproduce.
But it doesn't happen overnightand it doesn't happen by just
like giving people aggressivequotas.
(34:20):
Everything had to change.
We now have three segments, butreally a down market business
and an up market business andthose things are radically
different.
You know they're selling todifferent buyers with different
collateral, a different valueprop, a different value story,
the ROI and the way we tell thatbusiness value case completely
(34:42):
different.
And it's also on a differentcadence.
You know it's those enterprisedeals are slower, even in our
business and our cycles arequite short.
But you know it's a verydifferent thing than like down
market.
With startups our sales cyclecan be 16 days.
You know, with an enterprisewe're looking at 70 to 90, in
(35:05):
many cases a very traditionalcycle we're looking at more like
six months.
So you got to make the spacefor people to do that and it
takes time.
Sophie Buonassisi (35:15):
How did you think about evolving product and
go to market alignment duringthat shift?
Stevie Case (35:21):
Yeah, this was big and it is ongoing.
This will be a forever thing.
At the beginning I felt reallypassionate about this move up
market and so this is a littlebit of a I would say this is a
little bit of a counterintuitivebet.
(35:43):
I went go to market first atmarket.
This is kind of ill-advised.
This is actually not the adviceI would give most people, but I
felt really passionate about it.
I thought there was somethingthere and I thought I can build
a team and make the math suchthat I can send the team after
this opportunity and we canlearn what the market looks like
and we can use that to thenbring data back to the rest of
(36:07):
the organization and show theproduct team what we think we
need to really win up there.
So you know, in mostorganizations you want to go
product first if you're going tomake this move.
We did go the other way.
We went go-to-market first.
So what we did is we createdthis product feedback loop and
we really doubled down on salesengineering for the first time,
(36:28):
which was not a big functionback then for us, but brought in
our SEs and we started todevelop a point of view on what
is the product and what does itneed to be for us to win really
in the mid-market at that point?
For us to win really in the midmarket at that point, we had
frequent sort of voice ofcustomer meetings with products
(36:48):
and we were bringing them reallythe intelligence on who is this
buyer, what software do theyuse today, what are their needs?
And you know, little feature bylittle feature, we were just
asking them to sort of likebuild this future vision and at
that point we were not, as acompany, yet committed to that
(37:09):
upmarket product.
So it was, it was slow andplotting, and we were getting,
you know, we were beg, borrowand stealing like resources, and
convincing people to ship thislittle feature here, this little
feature.
And you know we made progressagainst it and we were able to
then go back and show like, oh,that really landed.
And we were starting to do allthe things you do like prove
(37:32):
that you've got a certain numberof pipeline dollars against a
certain feature request andstack ranking those.
And you know it was just a lotof conversation.
And at a certain point when wegot enough traction and we felt
like the product was thensufficient to meet this like
larger buyer need.
Then we actually had a formalconversation as a leadership
(37:53):
team and this was fun because Iworked on this with Chase Lee,
who came into Vanta as a VPproduct.
He was the CEO founder of acompany called Trustpage that we
had acquired.
So Chase was superentrepreneurial and he was
seeing the same marketopportunity as a VP product.
He was the CEO founder of acompany called TrustPage that we
had acquired.
So Chase was superentrepreneurial and he was
seeing the same upmarketopportunity and so he was on the
(38:15):
EPD side of the house and so Ikind of like he became my ally
in this and he and I made thecase we brought this to the
leadership team that we shouldmake a real material investment
in the millions of dollars, innot just go-to-market for
upmarket, but also in theproduct.
And we ended up greenlightingthat investment and that was
sort of the formal start.
But that didn't happen until agood year after I had put this
(38:38):
little go-to-market squad ongoing to prove the theory.
So it was a long journey to getthere, but then we had our
proof points and once that wasgreenlit then we really clicked
into.
Okay, we now have a businesswhere we're building two
separate things and, granted,it's one product, but the
product experience for a startupfounder is very different than
the product experience for, like, a CISO who's our upmarket
(38:59):
buyer.
So then we were starting tobuild different engines in the
business to take us after thosedifferent opportunities.
Sophie Buonassisi (39:10):
Why would you advise founders not to do that
and go product first instead ofgo to market first?
Stevie Case (39:16):
You have to be really sure.
It's really easy to getdistracted, especially by
inbound lead flow.
And this is a common thingbecause, honestly, every founder
what they should be focused onis getting product market fit
and then scaling that one thingthey do really well.
The failure mode for a lot offounders is like shiny thing
(39:38):
syndrome, where it's like we'redoing this one thing really
really well, but then, oh,there's this huge enterprise and
they said, if we do xyz and webuild these features for them,
they'll pay us a million bucksand like, oh, that would be a
big deal for us.
And then you get sucked intothat and then you kind of don't
account for the fact thatthere's like a huge amount of
support required and it canreally derail you from your core
(40:00):
mission.
So so I advise founders to goproduct first, because if you
try to force something like thatwith go to market, you can
completely randomize yourproduct development and you can
really take yourself off courseand end up slowing everything
down and kind of kill theproduct market fit of the thing
you had that was working in thefirst place.
(40:21):
So if you're going to go aftera new segment, you need to be
really, really sure there'ssomething there and that was for
me that, like the sign that itthat it was a bet worth making
at the time I did is one I hadhigh confidence in myself and my
own analysis and I deeplybelieved I saw something real.
(40:44):
You know, I had seen at Twiliothat journey from just serving
small companies to serving largeLike.
I joined as an enterprise AE atTwilio and they didn't have an
establishment of the enterprisesegment when I started we were
about 200 million in revenuethere and we only had enterprise
customers that were like bigtech scale-ups, so like Amazon,
(41:06):
netflix, these kind of companies, and we had a few but not a ton
.
When I left six years later,the enterprise business was a $1
billion run rate business and,like in my first couple of years
, I personally landed dozens ofFortune 500 logos there.
So I had seen that journey andI saw what it looked like at the
beginning.
(41:27):
When it you know, my firstFortune 500 deal, which at
Twilio was a $500 deal, like, Isaw that journey up to like $10
million deals and a billiondollar run rate.
So I knew what it looked likeand smelled like and I felt,
like at Vanta, I smelled it likeit was there and I could see
that there was something real.
So I was making a bet that Icould make the math work by
(41:53):
pursuing this like tip of thespear strategy with go to market
, going up market, because Ibelieved there was something
very real there.
And I also knew, like you know,it's a bet, it's an experiment.
If it doesn't work out, we canrecalibrate.
I wasn't confident enough atthe beginning to say like, let's
make that multi-million dollarinvestment on day one.
That's kind of why I went to goprove it out.
(42:14):
We sent this squad out to proveit out and luckily, what they
found was it was real and wewere able to capitalize on it.
Sophie Buonassisi (42:21):
And you probably wouldn't have had that
really high conviction if youhadn't worn those shoes at
Twilio and had that experiencefirsthand.
Stevie Case (42:28):
Yeah, exactly Because I had the confidence to
know what a successful, scalableenterprise business looks like
and I had seen the journey toget there and like what it
looked like on day one and thenwhat it looked like several
years later.
So because I had seen that andI knew how the math worked and I
knew how to increase deal size.
There's some very like, there'ssome mechanics in there of how
(42:49):
you can build a package forenterprises from something that
started as a small SMB product.
So you're right, I had theconfidence of having seen that
journey and I believed I couldreplicate it.
So and it's interesting inretrospect because you know
Christina hiring me in the CROrole most of my experience had
been enterprise, at least in themost recent years.
(43:11):
So she kind of brought me intothis very down market business.
I know her thesis at the timeis she wanted somebody that had
seen both, that had seen small,like developers and SMBs, and
somebody who had seen enterprise.
So I think that that ended uppaying off.
Sophie Buonassisi (43:29):
And it all comes full circle that moment
when you're questioning did theymake the right decision to?
Yes, they absolutely made theright decision.
Stevie Case (43:37):
Hopefully I've proven that out by now.
I do.
I definitely am coming from aplace of higher confidence at
this point, Like, yeah, it liketakes a while as a CRO.
This is the funny thing abouttaking your first CRO gig is
everybody's got advice.
Nobody really understands whatyou're dealing with.
You know, I remember at the verybeginning, actually, the first
(43:57):
person that the Sequoia teamconnected me with was Shant,
who's the CRO at Figma, and Iwas like, tell me what to do,
what is the job?
Where should I start?
And he had advice.
But he's like every business isso different and that's what
you come to realize is there'snot a playbook, you have to
(44:20):
build it for yourself and everyis so unique and it's a super
sink or swim job.
So like you can get theselittle nuggets of advice from
people but nobody can reallytell you how to do the job.
You got to figure it out.
Most CROs like 18 months isconsidered success in the CRO
role.
So I'm three and a half yearsin feeling good like I survived
(44:41):
to tell the tale.
But man, it's hard.
So you got to figure out how toget your hands on those gears
and on the levers and if you canfigure out how to make numbers
move.
That is really, at the end ofthe day, the job, and that
sounds really simple.
But trying to figure out how tomove metrics is actually quite
hard when you're.
The levers you've got are likedozens to hundreds of people and
(45:04):
you've got all these differentdynamics.
So I feel very lucky and andhere we are several years later
and we're having a blast.
Sophie Buonassisi (45:13):
And we're north of 100 million.
Were there any other pivotal goto market shifts along the
journey to get there that maybewe haven't covered?
Oh my?
Stevie Case (45:20):
gosh.
Yeah, I mean, the biggest ofthose, when I look back, was
actually not pre-sales, so had awhole journey there, you know,
getting new logo revenue goingup into the right.
But the next big inflection wasactually post-sales and you
know we had a very down marketbusiness.
As you can imagine, we sell tofounders and you know those like
(45:41):
net retention when you sell tostartups is naturally going to
gravitate lower.
If you just look at averagesacross the industry, you know
companies who sell to SMBs aretypically hovering around 100%
net retention, whereas if you'reselling to enterprises to 120,
140.
And as you get to biggerrevenue targets and the law of
(46:02):
big numbers becomes real, netretention has to go up.
So that was my second sort of18-month journey was figuring
out how to get my hands on thelevers in post-sales and drive
gross retention up, butespecially drive net retention
up.
We had no real expansion motion.
(46:23):
When I started we took on acustomer success team.
It was a big team.
They were being asked to doeverything renewals, expansion,
customer education and healthadoption, like everything and it
was totally set up for them tofail because their job was like
a hundred different things andyou can't succeed when your job
is a hundred different things,and so there was this journey to
(46:46):
redefine that team.
We broke it into two piecescustomer success and account
management.
That's evolved.
So customer success now ownsgross retention, account
management owns renewal andexpansion.
I hired an incredible leader inthere, kelly Bray, who leads
all things post sales for me,who is just crushing it.
And similarly, it took abouttwo years.
(47:08):
We had to build a sales enginein post sales and you know that
has been wild and we've moved,you know net retention of double
digit numbers and that was noteasy.
And it's another one wherethere's no playbook.
Everybody does post sales verydifferently.
(47:29):
It's even less standardizedthan sales.
So huge learnings in there, andI've been so grateful to have
Kelly as a partner in it and Ithink we're doing some really
kind of groundbreaking stuff inpost sales today, like where you
got to.
It's one of those unique thingstoo, because it's not just
selling stuff You've got,there's the entire customer
experience You've got to.
You know, ensure customersadopt the platform, that they're
(47:51):
satisfied, that they have agreat quality experience, and
then you want to tell them moreabout the rest of the platform
and and get them to adopt evenmore of what Vance has built,
cause we built a lot of productsover the last year.
You know we aren't just nowkind of that core compliance use
case.
We do vendor risk, we docustomer trust, we do
questionnaire automation.
You know we've got this wholesuite of products so that
(48:15):
post-sales team have to be trueexperts on the platform, as they
are also serving our customers.
So big journey there as welland a lot of learning.
That was a new one for me.
Sophie Buonassisi (48:25):
What approximate year was that, would
you say?
Stevie Case (48:28):
I took that on initially about nine months into
my tenure to start and you knowI would say the first six
months I was really just gettingmy hands around like how does
this even work?
Like how is this team workingtoday?
Like what are the basics here?
Going out and I do anytime Itake on something new I go out
(48:49):
and talk to as many people as Ican, so talking to tons of
customer success leaders andaccount management leaders, just
talking to anybody I can talkto to understand how they do it.
So it's about six months ofinvestigation.
Then we started transformationand you know the first
transformation was that breakingthe team into customer success
(49:09):
and account management, so twodifferent functions and that
first change was about 12 monthsafter I took on the team and
then from there that was a goodyou know.
So it's been, you know, acouple of years since we made
that change and there's been alot of incremental change since
then.
So we're about two years intothe journey and we it took about
(49:30):
a year and a half to really seethat start to pay big dividends
.
Sophie Buonassisi (49:36):
We're hearing the pattern of starting
initiatives and really waitingand having the patience to see
it pay off, as opposed to theimmediacy.
Yeah, so time, yeah, yeah.
And Steve, you now, I meanyou're north of 100 million ARR
and Series D.
Congrats again.
What's the next biggo-to-market focus for you and
where are the opportunitiesahead?
Stevie Case (49:57):
Yeah, I've got a couple of big ones over this
coming year.
So one is really sell theplatform and what that means for
us is just like when I arrivedand we kind of had one sales
team and no segments.
We now have multiple segments,this broad team, but that broad
team is really selling the coreplatform.
The reality is we have shippeda lot of other incredible
(50:20):
products.
This vendor risk product that'sbecoming a true third-party
risk product.
Our entire customer trustplatform.
We've got these other elementsin the platform.
We've got an access reviewproduct.
They can in many cases be soldstandalone.
So now a lot of the mission islet's go sell those as true
(50:41):
standalone products to differentbuyer personas and it means
really creating separate teamsand muscles and motions in our
go-to-market engine.
So that's a big one.
That's a huge area ofinvestment.
We've got killer products inthese areas.
But again, like the productsdon't sort of like figure out
how to sell themselves.
(51:01):
You've got to go figure out howto build a funnel for each one,
how do you identify buyers, andthen you've got to create the
space for a team to actually gosell that and not it's
counterintuitive, but like notget weighed down by the success
of the core product.
So if you give everybody youknow the whole platform to sell,
they're going to sell the corething that sells.
Well, they won't pay attentionto, like the products that are
(51:21):
emerging.
So you got to create space forsomebody to focus on just
emerging products.
So that's the one big one.
The next big one is really goingto be what we're calling Vanta
for government public sector.
We just went down this path andjust last week got our FedRAMP
20X low authorization, which isa big deal.
(51:44):
It's like the federalgovernment is doing this pilot
program to essentially expeditepeople being able to be fedramp
compliant, which now allows themnot just to sell to the federal
government but in our case itmakes it so we can help other
companies become fedrampcompliant.
So they're sort of like sellingto the government and then
they're selling to othercompanies who sell to the
government as well.
(52:05):
Massive opportunity for us.
We're really excited about itand we are committed to that
journey to really work in thatfederal ecosystem.
So, building out a publicsector function, bringing in
leadership there and doublingdown on our opportunity there is
another big area.
And doubling down on ouropportunity, there is another
big area.
And then the third is thecontinuation of the journey
(52:25):
we're on, which is servinglarger and larger enterprises.
So we do serve today atremendous number of large
enterprises.
We've got customers in theFortune 100.
We are selling to not just techscale-ups but like true kind of
old school enterprise logos,and so continuing down that path
and serving their needs aroundgovernance, risk and compliance
(52:48):
is going to be a big part of themission over the next year.
Sophie Buonassisi (52:52):
Incredible Well excited to see all of that
in execution.
And, stevie, I've got to askyou how are you using AI
personally and in Vanta andlearning about AI?
How are you?
Stevie Case (53:04):
using AI personally and in Vanta and learning about
AI.
Yeah, we've got a couple of bigangles here.
So I am a big believer in AI.
I am very bullish and, honestly, like what we're doing at the
heart of it is sort of remakingthe way we think about revenue
operations.
So historically, revenueoperations teams were more
system admins, not necessarilybuilders and folks who wrote
(53:26):
code.
We are moving in the directionof building an AI builder
function within revenueoperations.
We've already got a teamstarted there.
So we are infusing AI intobasically every workflow every
workflow.
So all of the basic things youwould think of like updating CRM
with AI, delivering pre-callprep notes to our teams with AI
(53:52):
all of those workflows now exist.
Now we're starting to thinkabout some next stage use cases,
like we're bringing in anagentic platform to help bring
customers through onboarding ina really interesting way.
We've, of course, infused it insupport, where we can really
shorten response times and getgreat high quality responses.
So like we're building iteverywhere At the same time, we
(54:15):
are making a bet on humans.
So I look at AI and go tomarket as an opportunity to
allow our humans to do thehigher value work and really up
level the way they function.
So big investment on both thetech and humans.
Personally, I am having a blastwith it.
I love it.
I ended up buying an entirelynew laptop so I could experiment
(54:36):
and just sort of go wild.
Sophie Buonassisi (54:38):
I love it.
Stevie Case (54:40):
Oh yeah, I'm actually building an app right
now.
I've been playing around withboth Cursor and Replit and
having a ton of fun with that.
I'm, of course, obsessed withChatGPT and use it for basically
everything in my life foreverything from fun things and
(55:06):
sort of entertainment tointerpreting my lab work when I
can't get ahold of my doctor to.
I actually did my taxes thisyear with the help of chat GPT.
Highly recommend TurboTax pluschat GPT magical combination
totally worked for me.
So you know, I I'm a believer.
I know there are a lot ofskeptics and they'll say, like
you know that you should not,but I don't know.
I've had a great experience andI'm bullish.
(55:29):
I think that you know.
Ai gives us the opportunity todo things that are more human
and can take out that minutiae,and I'm enjoying it.
Sophie Buonassisi (55:41):
What about the other side of the coin from
AI?
Are there any books that you'veparticularly enjoyed and that
you'd recommend to anyonelistening?
Stevie Case (55:49):
Yeah, it's a great question.
So right now I am reading abook called Endurance, not a
business book but kind of aleadership book.
You know it's great.
It's about this shipwreck andkind of the way that this crew
led themselves out of this verydire situation where they were
shipwrecked in, of the way thatthis crew led themselves out of
this very dire situation wherethey were shipwrecked in a very
bad situation Book that wasgiven to me by Varun, the COO
(56:13):
and founder over at Clay Greatcrew.
So that's what I'm enjoyingright now.
I do a lot of business books aswell, as you can imagine.
So it's kind of nice to get alittle respite from the business
books.
And there, you know, you got todo all the classics, the like.
You know the, the Slootmanbooks, you know the qualified
(56:33):
revenue leader, always a fan ofthe classic challenger sale,
like I still think that lands.
I still go back to thatstructure.
So, yeah, all all of those aregreat, but I'm trying to take a
break it's summer and readsomething a little more off the
beaten path.
Sophie Buonassisi (56:50):
Yeah, yeah, fair enough.
And where can people find youif they want to get in touch or
follow your journey?
Stevie Case (56:57):
Yeah, they can find me on LinkedIn, so I am posting
on LinkedIn super active, loveto connect there, so come find
me Awesome.
Sophie Buonassisi (57:05):
We'll pop it into the show notes, Stevie.
Thank you so much for joining.
Congratulations again on theSeries D, and we can't wait to
see the continuing progress thatyou and Benta have.
Stevie Case (57:13):
Thank you so much.
It's been great being here.
Sophie Buonassisi (57:16):
Awesome To everyone listening.
Thank you for joining us andwe'll see you next week.
Every business is subject to the laws of physics
and math.
It looks magical from theoutside.
Every one of those businesseson the inside felt like chaos.
We had 40 plus copycatcompetitors.
It was wild.
Execution is the only mode.
Nobody cares if you were first.
Sophie Buonassisi (00:39):
Before we jump in, let's talk about
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(01:22):
Today on the podcast, stevieCase, cro of Vanta.
Vanta just raised a $150million Series D and is now
valued at over $4 billion.
Stevie took the company fromSMB to enterprise, battled over
40 copycats, rebuilt both preand post sales engines and
continues to lead revenue at theunicorn.
In this episode you'll learnearly growth decisions, her
(01:43):
first hires, her systems, whatshe deep prioritized, how she
tested and scaled to enterprise,how Vanta beat over 40 copycats
with pricing strategy, valueselling and a CIA competitive
squad.
How they drive expansion andwhy execution is the only moat.
We're proud to be an earlybeliever in and backer of Vanta
(02:03):
as an investor.
All right, let's get into it.
Stevie, welcome to the podcast.
Thank you, so excited to behere, so excited to have you,
and I mean what perfect timingwith all the momentum that
Vanta's experienced.
Huge congrats to you on theraise.
Stevie Case (02:18):
Thank you.
I feel really lucky.
We're still having a lot of fun.
Sophie Buonassisi (02:22):
That's the goal right.
You can scale and have fun atthe same time.
That's when you know that'sright Incredible.
Well, take us back a little bit.
You know, maybe even before youjoined Vanta, you've got an
interesting background.
Love to unpack that a littlebit and how that led you to
Vanta.
Stevie Case (02:41):
Yeah, I've got a very non-traditional start to my
background.
So I started at well.
I started out in collegethinking I was going to be a
lawyer and I was pre-lawpoli-sci doing that path and I
kind of fell in love with videogames and ended up becoming the
world's first female pro gamerworld's first female pro gamer.
(03:07):
And that was a long story, longseries of events, but there are
some common threads and thatearly beginning as a competitive
gamer really put me on thispath towards making games, which
games are really just softwareat the end of the day.
So then I was a product managerand ultimately ended up getting
offered an opportunity tobecome a salesperson.
Ultimately I ended up gettingoffered an opportunity to become
(03:27):
a salesperson, learned how todo that and over time my
portfolio started out as 100%video game companies and became
more and more mainstream tech.
And years later here I am and Ithink honestly I look back and
it seems a little crazy likeit's a path that doesn't make a
lot of sense on paper, but thereare absolutely common threads.
Path that doesn't make a lot ofsense on paper, but there are
absolutely common threads and myintense competitiveness is
(03:48):
probably the single unifyingthread from start to finish.
Sophie Buonassisi (03:53):
I love it.
I always think we think aboutcareers too linearly in a way,
so there's always a commonthread.
It's more of an ecosystem thanone linear path.
Stevie Case (04:03):
Absolutely.
I'm a big fan of really leaninginto things that are
uncomfortable and I love tochallenge myself and love to
grow.
And you know, if I had set outand designed a career early on
that was only made of thingsthat I knew about at the time, I
wouldn't have gone very far.
(04:23):
You know, I grew up in KansasCity, kind of outside of Kansas
City, in the country.
I had no exposure to business,I had no exposure to a lot of
things, and so I've been reallylucky to get these opportunities
where I've been able to expandthe universe of what I am, what
I even know about and what I getto be in the room to talk about
(04:43):
.
And so I've done that.
I try to find those littleedges that are a little more
unknown or maybe a little moreuncomfortable, and I tend to
embrace those and sort of diveright in.
Sophie Buonassisi (04:55):
Incredible and you go from smaller towns
pro gamer product manager toVanta.
What was Vanta's revenue andgo-to-market setup when you
joined?
Stevie Case (05:06):
Yeah, we were much smaller so Vanta.
Today you know we're north of athousand people.
When I started we were lessthan 200 people.
We were single double digits ofmillions in revenue, digits of
millions in revenue.
So like pretty early on thejourney when I joined I just
(05:31):
started with North Americansales only.
So when I joined on day one Ihad about 20 people on my team,
mostly sales people, and it wasvery early days.
There was a ton of excitement.
It was super clear.
There was this very intenseproduct market fit, but from a
go to market perspective, not alot of structure.
(05:53):
It was 100% inbound, not usingCRM in a meaningful way, no
forecast cadence, like you knowit was.
The vibes were high but thestructure was not really
existing yet.
So I kind of liked that.
It was a.
It felt like the Wild West ofit at that time.
Sophie Buonassisi (06:12):
Hey, better than the opposite.
Right, that's right, that'swrong.
The vibes are high.
All the structure can bebrought into place.
Yeah, what made you believethat it could scale to be an
$100 million plus company?
Stevie Case (06:25):
Yeah, you know I really I struggled with that
question because I think it'seasy to look back and say, oh, I
saw this thing and it was soobvious.
I don't think that's often true.
And there were some things atthat point with Vanta that made
it clear that the long termpotential for the company was
(06:47):
massive and the biggest of thosewas, honestly, just the product
market fit was off the chartsand you know people debate what
that means or like how do youknow you've got product market
fit?
What I can tell you is peoplewere coming inbound at a wild
clip and when we would get onthe phone with founders we were
(07:11):
seeing one call closes.
We were seeing just these likeoh my gosh, please give it to me
now, because you are solving apain that is so intense and so
significant.
And at that time our first usecase was helping founders get
SOC 2 compliant for the firsttime.
And so they were coming to usand saying I have a customer
(07:32):
deal and it's requiring thiscustomer's requiring that I have
a SOC 2 audit complete and thatI can give them the report to
get the deal done.
So it was revenue blocking andI really liked that because you
know people only really buy forthree reasons.
Right, it's either going togrow revenue, it's going to
reduce costs or it's going toreduce risk.
(07:53):
At the end of the day, thoseare the only three reasons
people buy things and of those,growing revenue is a much more
compelling reason to buy thansome of the other reasons.
So to have that as our primarymotivator was huge.
And so to see there's this likereally intense pain.
It's a revenue blocker.
There's a lot of inboundinterest and in that process of
(08:16):
getting to know the company, oneof the things I did was one of
the salespeople gave me a demo,so I got an AE to give me a demo
.
Salespeople gave me a demo, soI got an AE to give me a demo.
And you know it was fascinatingbecause it was, in some senses,
the demo was super simple.
The sales process was supersimple.
There was nothing.
There were no, there was nolike over the top sales magic to
(08:37):
drive these deals to close.
It was like that compelling ofa product.
So for me, that was the likeokay of a product.
So for me that was the likeokay, this is very real and we
can clearly sell more of this.
There's a lot of demand.
The thing that I questioned andthis came later was sort of
like where does it go from there?
And that became the bigquestion of the next era.
Sophie Buonassisi (09:02):
And was there a moment early on when you had
that question in your mind,where you thought you might have
made the wrong call?
Stevie Case (09:11):
You know I don't know that I ever felt like I
made the wrong call, but therewere some times that were very,
very hard.
You know, even in the beginning, as I was debating joining, you
know I talked to Andrew Reidfrom Sequoia, who's on the board
Vanta, and you know I wasasking him sort of like where
does this go from here?
(09:32):
Like this is obviously great,we've got good product market
fit, founders love us, but we'reselling to very small companies
and we're selling very smalldeals.
And you know I'll never forgethim saying this was like a
Sunday night, as I was trying tolike make this decision Sunday
night at like 11pm or something,and I'm on zoom with Andrew and
(09:53):
I'm like it's a great wedge,but like to what?
And he said I don't know, butit's a hell of a wedge and like
there was like something in that.
And you know, like therecognition, I was like okay, I
actually can roll with that.
Like I am totally good withambiguity, I can, I am a big
(10:13):
believer, I love to bet onmyself and I think Christina,
the founder of this company, isbrilliant, like I want to bet on
her.
So the bet was we've gotsomething really great and a lot
of product market fit.
We're going to figure it out.
And that became like my first 18months.
So there was a lot of work.
We had a lot of copycatcompetitors.
We had like a whole thing to doin that first 18 months and
(10:37):
then we also had to figure outwhere we were going as a company
in the future.
And you know, in that first 18months there there were some
extremely hard times.
You know, we were in a revenuerut for a long time where three
or four quarters in a rowrevenue didn't really grow.
And when you join as the chiefrevenue officer and you can't
(10:58):
grow revenue, it's not good.
So I wouldn't say I thought Imade the wrong choice.
Necessarily I thought maybethey made the wrong choice.
I was definitely.
Yeah, I mean, at the time,though, I was like I don't, I
can't, I can't crack the code,like I'm showing up every day
trying to figure out how to makerevenue go up and to the right,
(11:21):
and like I cannot crack thecode and I'm like trying
everything I can think of.
So you know, we did it.
After about 12 months, thingsstarted to inch up into the
right and then, about 18 monthsin, it was like okay, okay, we
figured this out.
We figured it out.
I figured out how to getrevenue to go up into the right,
(11:42):
but, man, it was not easy.
It was not easy.
Sophie Buonassisi (11:47):
And I feel like those are the common
sentiments you hear from anyonein the early days.
It's easy to see VantageousSeries D now and think, wow,
that's incredible.
But there were people in thetrenches yourself and others,
christina and everyone just justyou know working day in and day
out to make it go up into theright, so really it's a
testament to that.
Stevie Case (12:06):
I mean, I think that that's for me, the biggest
lesson, because you look back onthis and it's like, okay, it's
an obvious success and I justdon't know that.
That is true pretty muchanywhere.
You know, you look at all thesecompanies Figma IPO'd this week
and you listen to what theywent through and incredible
(12:28):
product, but it wasn't linear.
You know, it was hard and thatwas of those first 18 months.
I think the biggest lesson init was every business is subject
to the laws of physics and mathand while it looks magical from
the outside and like there'sfairy dust and it's just
(12:49):
happening, and like revenueshowed up and the growth was off
the charts, it is so true that,like every one of those
businesses on the inside feltlike chaos, had to grind so hard
, hit so many obstacles wherethey couldn't figure it out or
it didn't make sense.
And the proof point that I liketo take for that with Vanta is
(13:11):
that we had, at one point, 40plus copycat competitors.
Wow, it was wild and this isone of the reasons I was brought
in as CRO is we had, you know,vanta was the first to market.
Christina created this marketand this concept of the product
brought it to market first.
(13:32):
We then had several companiessee the product market fit and
go, oh, we can build that.
So they, you know, in somecases went off and like, built
an offshore copy and like athird party dev shop and and
then came with flashy marketingand we're like, oh, we're Vanta,
just half the cost.
And we went through this entirephase where, you know, it felt
(13:55):
to us and, I think, to some inthe market, like some of those
copycat competitors were winning.
And what I learned through thatprocess?
I learned a lot through thatprocess, but one of the biggest
things I learned is that you canfool people with marketing for
a little bit and you can usethat as a cover to create a ton
of momentum.
But every business is stillsubject to those same rules, the
(14:18):
same math.
You're still.
You still got to figure out howto get your net retention to be
positive.
And on the up and up, you stillgot to figure out how to get
your net retention to bepositive.
And on the up and up, you stillgot to figure out how to drive
real sustainable growth.
You still have to build ago-to-market engine.
And you know, flashy marketingand software built cheaply
offshore, it doesn't really getyou there.
(14:41):
So you know I'm grateful forthe lesson.
It doesn't really get you there, so you know it was a I'm
grateful for the lesson.
We you know we we have pulledaway from the pack and that has
been incredibly gratifying butwas not easy.
Sophie Buonassisi (14:52):
Incredible, I think I mean more than ever.
Now.
There's copycats popping up andit's a common challenge for
other companies, for otherfounders, for early stage
go-to-market leaders, for othercompanies, for other founders,
for early stage go-to-marketleaders.
How would you advise othersagainst that?
You know you've combated 40plus other copycats.
Stevie Case (15:18):
How do you win?
Yeah, well, I mean, I am a bigbeliever that execution is the
only mode.
So you know, nobody cares ifyou were first, nobody cares if
you originated the market or youknow that you've been in it
longer.
They just want to know that youare going to give them the most
value and that they are goingto be well taken care of and,
ultimately, that you've got thebest experience that's going to
help them achieve their goals.
Like that is all customers careabout.
(15:39):
So my advice to folks who getinto this situation because it
is so common now you'll seethere's a successful business
Immediately.
People go out and buildcopycats and sometimes that
number two ends up winning, andthere are some key things you
can do in there to head it off.
So you know that focus onexecution at the heart.
The things you got to do.
One is put your head down andstart going faster.
(16:03):
You know, use it as anopportunity to say, okay,
there's something here we needto now speed up and up our game.
So you got to really gettighter on your execution.
A couple of the key tacticalthings that I think really make
a difference.
One is you really have to focuson value.
This was the big transition thatwe made as a go-to-market
(16:26):
organization in my first 18months is we went from a inbound
transactional sale.
We used to say it was kind oflike do you need a pen?
I have a pen.
It was very, very sort of weknow what we have is valuable.
You need the thing?
Here's the thing.
Discovery-wise, we were doing asimple version of Bant.
(16:47):
It was just like super, youknow Bant, here's the demo.
Great, here's the order form.
We had to move from that to areally different value based
sale with much deeper discovery.
So we had to get really curiousabout why our customers were
buying and why they wereinterested in us, what the pain
was.
So train the team on MedPickand really started to enforce
(17:10):
that and like dive deep into theart of discovery, which is
something I'm super passionateabout.
It's like anytime I work withfounders or anybody trying to
build a sales team, my numberone piece of advice is like
learn how to do great discovery.
If you do that like, it's hardto go wrong.
Everything else is kind ofextra.
But if you do great discoveryand you're super curious and you
ask those second and thirdlevel questions, you're you're
(17:33):
going to be on a great path.
So that's one.
Two, then, was to quantify thevalue of our platform.
So it wasn't just here's thesoftware, here's the features
and functions.
Do you want to buy it?
It was, okay, let's understandthe pain in your business.
What are you trying to solve?
Okay, this is blocking a deal.
What's the deal worth?
When do you need to get thedeal done?
(17:54):
What are the resources you haveto take this project on?
Let's start to quantify that.
And then we were able to tell astory of the revenue that we
could unblock, of the resourcingwe could save, the time we
could save, and we were able tothen compare to those cheaper
competitors in a very favorableway, even though we are a
premium solution.
We were able to prove it withmath that we were delivering
(18:18):
more value for every dollar.
That focus on value is at theheart of it.
And then, from there, there'slike a lot of little tactical
things we did beyond that valuetransformation.
Things like we created acompetitive takeout squad and
they weren't on quotas, theywere just on a takeout target.
So they became our experts onthese competitors and they
(18:40):
learned them inside and out andthey just developed the perfect
talk tracks called them the CIA,the Competitive Intelligence
Agency, and this squad of folks.
They were doing their own deal,so they were going trying to
like, rip customer logos andthey'd go down all the logos on
the competitor's website and tryto take them away.
They would also get on callswith the rest of the sales team
(19:02):
and be that voice of like here'show you win and here's what we
know and here's why we knowwe're a better solution for you.
So there was just a lot oftactics in there and at the end
of the day, it was all aboutbuilding confidence that what we
were saying was true we havethe better solution, we can
deliver more value and we'regoing to give you a better
experience.
Sophie Buonassisi (19:26):
And that was one of the challenges that you
faced in your first 18 monthsthe 40 plus copycats.
Take us back to the beginningNow.
What was the state of revenue?
And then you mentioned thego-to-market engine.
Where it was.
What were your first moves froma go-to-market standpoint to
actually scale?
Stevie Case (19:41):
Yeah, I mean, in those early days the state of
revenue, honestly, was unclear.
One of the biggest challenges Ihad at the very beginning is
that we had no measurement, andthis is actually one of the
biggest mistakes I look back at,because I came I came from
(20:03):
Twilio where I was mentored byour CFO, george Hu, who at his
core, is really an analyst likeso deeply, deeply math driven I.
That is how I lead a team aswell.
It's very math driven.
But when I arrived at Vanta, wedidn't have the.
We didn't have any analyticsinfrastructure, there was no
measurement.
I could not see anything andwhile I pushed to build that
(20:29):
function and that team, I kindof accepted the no.
When I got the no and I wastold oh, we've got a product
analytics team, use what they'vegot, it's fine.
I accepted that and that isprobably the single biggest
mistake I made when I look backon it, because it meant I went
about a year without reallybeing able to see what was going
(20:52):
on in my business and it led meto make some incorrect
decisions along the way, becauseon arrival, you know, one of
the first pieces of advice I gotwas you need to hire like
there's a ton of demand.
We're not serving that demandadequately.
Like hire people.
So I went out and I hired abunch of SMB sellers, like very
(21:12):
junior SMB sellers, because atthe time the business looked
like a very down market business.
And you know, the thought atthe time was we can hire junior
sellers at you know a fairly lowcost and they can still be
effective because our win ratesare off the charts.
But I couldn't.
I couldn't measure anything.
So I was going on instinct andadvice and what we found was we
(21:33):
brought those people in and won.
The competitive landscapeshifted and our win rates went
down and we found that the salewas actually more complex than
it appeared to be from theoutside and one of the things
under the covers was that thecustomer base of prospects were
a little more complicated thanwe thought.
(21:53):
It wasn't just sort of downmarket tiny startups and
founders.
There was like enterprise mixedin there.
There was like some interestingkind of blend.
There was like enterprise mixedin there.
There was like some interestingkind of blend.
And so these SMB like firsttime sellers were struggling.
So for the first time we hadfolks come on and like miss
(22:13):
quota, and that was rough.
So, going back to that, it waslike that was my first mission
was hire.
And then I hired and it didn'twork.
And not only did it not work,we had people join that didn't
hit quota.
It obviously diluted theinbound lead flow.
So then you've got people thathave been here a long time who
were like kind of with not a tonof effort, doing like 300% of
(22:34):
quota, who are now like maybesort of making number and maybe
not consistently and, as you canimagine, that like crushes the
spirit of a sales team For sure.
So it was like this very toughmoment and there were a lot of
lessons in there.
For me, number one was nevercompromise on your measurements,
like you have to be able to seewhat's going on before you make
(22:55):
real decisions, otherwise youare bound to fail because you're
going to make assumptions andyou're going to get it wrong.
Number two was really likeconfidence in a sales team
matters more than a lot of otherthings and keeping morale high
and confidence high isfundamental to a winning culture
.
So lots of lessons learned inthere.
(23:16):
But you know we recalibratedand changed the plan.
Sophie Buonassisi (23:22):
And where did you pivot from there?
What were the most defininggo-to-market shifts after that
point?
Stevie Case (23:28):
Yeah, the next big one was we had to really
recalibrate.
At that point as a business.
A couple of things had becomeclear.
One was I had gotten the talentprofile wrong, so we had hired
the wrong kind of folks, and tome that is one of the worst
mistakes you can make, becausethese are people's careers and
(23:52):
you've just hired them into ajob that they're probably not
set up to succeed at.
So, like on a human level, thatwas kind of devastating.
So we had to recalibrate onthat.
We knew we had to up level thetalent.
The second thing we learnedthrough that is, you know, I did
not own marketing at that timeand we had sort of made this
(24:13):
growth plan together and we weregoing to double the size of the
sales team and marketing hadagreed to, you know, double the
inbound pipeline, because atthat time marketing was
responsible for 85% of thepipeline.
Well, not only did I get thehiring profile wrong, marketing
was not able to double pipeline.
So we hired all these folkswrong profile and then we did
(24:35):
not feed them and we did nothave the wherewithal to really
drive outbound at scale yet.
So we ended up in this positionwhere we had a team that wasn't
getting enough inbound, wasn'treally able to close as much of
what they were getting as theycould before.
And then, you know, we had tomake some tough decisions.
(24:57):
So we scaled down the size ofthe team a bit recalibrated,
started to build in moremeasurements, we up-leveled in
marketing and we decided to sortof give it a second go, but in
a much more math-based way.
So this time we, you know,locked hands and had an
(25:21):
agreement that was math-basedand we started to go forward
with a little bit more seniortalent.
We went a little more slowly andwe started to, instead of like
just making big bets and likehiring a bunch of people to go
do something, we started to geta little more incremental.
So in go to market, for example, you know, we started hiring a
(25:42):
slightly different profile ofperson.
We just hiring a slightlydifferent profile of person, we
just hired a few, we saw howthat went and then we would
incrementally add a little bitmore.
So it was a much more measuredapproach.
We also took that realizationthat there was a little bit of
enterprise and mid-market in ourpipeline and what I wanted to
(26:04):
do was start to go after that ina meaningful way.
So we broke out a team for thefirst time.
We segmented.
Basically we had just had asales team.
There was no segmentationbefore, so segmented, built a
team that was specificallytasked with working the sort of
like lower mid-market to smallenterprise leads.
Started small with that, butthat was the first time we
(26:27):
really broke into two teams, twosegments, and then we started
to think about that opportunitya little differently.
That muscle obviously isextremely different.
The sales cycle looks very,very different than the down
market one, so we wanted tocreate the space for them to go
after that.
So that was one of the next biginflection points was that
split of like okay, this isn'tjust a business that sells to
(26:48):
startups, we're going toactually go after something
different at the same time.
Sophie Buonassisi (26:52):
And it sounds like the signal for that was
you had inbound in your mix andwhen you created this team, was
it experimental?
Were you fairly confident thatthis would work and be your
wedge to go up market?
Stevie Case (27:05):
It was experimental .
It was experimental and youknow, the thing that I saw was
there was enough inbound frommid-market and enterprise in the
pipeline that I knew there wassomething there, but I, like I
did not know enough about whatthat thing was Like.
We knew the use case downmarket was this you know, first
(27:26):
time compliance for founders andwe had then expanded the
platform and we had added otherframeworks so we were supporting
things like ISO and HIPAA andGDPR.
So we were kind of expandingwith founders as we went up
market.
We just did not know.
We did not know what was thereand there was a whole space up
there, it turns out, calledgovernance, risk and compliance
(27:49):
where these so we were startingto there compete against a
totally different cohort ofcompanies.
So legacy platforms like Archerand One, trust and Diligent and
(28:16):
MetricStream these companiesthat, like frankly, I'd never
heard of and we started to seethem in deals and it was a tiny
team to start.
It was very much an experiment.
I set the expectation that,like this is going to take time
to work and we need to do theright thing by the team, which
means, like giving them a littlemore ramp, giving them a little
(28:37):
bit more buffer running, morespiffs, like giving them more
space to learn, because we don'tknow what we don't know.
But they did.
They started to build a littlemomentum and you know our
original head of sales, he tookthis on as a project to help us
build this upmarket team and,like that small team started
hitting numbers.
So we started growing it and,you know, just started trying to
(29:00):
kind of learn and like tryingto learn even the vocabulary of
that upmarket buyer, which wasextremely different from that of
the founders we had beenselling to.
Sophie Buonassisi (29:10):
Because it was experimental and that's
great that you got traction.
But how did you forecast that?
Stevie Case (29:16):
Yeah, you kind of can't Fair enough.
That in and of itself wassomething we had to get
comfortable with and this hascarried through the journey.
So when it started as anexperiment, you know, one of the
agreements at our leadershipteam level was this is an
experiment and the same mathcan't apply.
(29:39):
It's not fair to take AEs whoare going into a segment we've
never sold into, we don't evenreally understand what the
market looks like, we don't knowthe dynamics, we don't know
what the sales cycle is going tobe, and then hold them to some
artificial standards.
We did put them on quotas, butthen we really tried to do right
by them.
Frankly, we didn't, at the topline, count on the revenue.
(30:02):
We just, you know it was extra,it was bonus and we have
continued to build that way.
You know, the second year wedid that it's like okay, there's
something here.
Then we built it into more of atrue enterprise team.
But you know, in a normal salesorg you're going to forecast
that that team is going toattain a healthy amount of the
(30:23):
rolled up quota.
You know, 70%, 80% depends onthe segment.
With this enterprise team, youknow we started out the first
year and we said, we are onlygoing to count on them hitting
50% because we just don't knowwhat we don't know.
So we'll apply some math andwe'll test against it, but we're
going to set expectations lowand then we're going to work to
take care of our people alongthe way and make sure they all
(30:44):
are getting, you know, takencare of for helping us figure
out this new segment.
But as a business we can'tforecast it.
You have to get comfortablewith that and I think this is
one of the biggest mistakes thatpeople make.
When they enter a new segment,or even, honestly, when founders
make a first sales hire, theyfeel like, oh, I have to put
this person on a quota and itneeds to be an industry standard
(31:06):
quota, and if they don't hitthat fairly quickly, things are
wrong.
It's a huge mistake because youjust don't know what the right
math is and if you don't createthe space to figure it out,
you're going to be doomed tofailure.
You know I work with a lot ofsmall companies.
(31:27):
Worked with one recently andthey told me a story I've heard
a million times, which is theyhad an early sales team.
They were paying that salesteam a lot of money, and this is
true often when businessesstart they're like, oh my gosh,
salespeople make a lot of moneyand it makes them uncomfortable,
like these salespeople aremaking a lot of money, they're
not hitting their target.
So what this founder did was hefired that sales team and he
(31:51):
hired a way more junior, cheapersales team and then put them
against a quota and he said,looking back, he's like that was
probably a mistake.
Yes, that was a mistake.
Just because you've gotexpensive salespeople and
they're not quite hitting quota,that doesn't necessarily mean
your solution should be getcheaper salespeople.
You've got to figure out how togive them the space to get to
(32:13):
productivity and in the case ofmoving up market, that could
take years.
That might not be a one quarteror two quarter thing, that
might be a two or three yearthing.
So you got to have the patience.
Sophie Buonassisi (32:25):
Great advice overall, with the patience and
what time frame were you whenyou started this upmarket
experiment?
What year are we looking?
Stevie Case (32:34):
at.
This was like six months intomy tenure, so we're looking at
like mid 2022.
Like this is early, early in mytenure at Vanta.
So we're now three years in tothat journey.
Sophie Buonassisi (32:47):
How long did it take for you to gain true
enterprise traction from thatexperiment mid-2022?
Stevie Case (32:54):
From that point to get real enterprise traction two
years, maybe even a little more.
You know we had wins Not to saywe didn't have wins but there's
a difference between gettingthese sporadic kind of lumpy
wins and getting to somethingthat can actually scale.
(33:17):
And we hit that point where Ifelt like this team has scalable
success towards the end of lastyear.
And that's the point at whichit's like OK, we believe that we
can hire new reps and know howlong it's going to take them to
ramp and be relatively confidentthat we can give them enough
(33:39):
pipeline and that they can hit areasonable percentage of their
quota.
And if you can do that and youcan put more reps on the team
and you can repeat that playbook, then you know you've got
something that can scale.
And that does often take yearsand it did.
It took two, two and a halfyears for us.
(33:59):
And now that we're there, it'sphenomenal and they will be, you
know, a huge percentage of nextyear's target.
You know there are a materialpercentage of this year's target
.
So we do count on them now toproduce.
But it doesn't happen overnightand it doesn't happen by just
like giving people aggressivequotas.
(34:20):
Everything had to change.
We now have three segments, butreally a down market business
and an up market business andthose things are radically
different.
You know they're selling todifferent buyers with different
collateral, a different valueprop, a different value story,
the ROI and the way we tell thatbusiness value case completely
(34:42):
different.
And it's also on a differentcadence.
You know it's those enterprisedeals are slower, even in our
business and our cycles arequite short.
But you know it's a verydifferent thing than like down
market.
With startups our sales cyclecan be 16 days.
You know, with an enterprisewe're looking at 70 to 90, in
(35:05):
many cases a very traditionalcycle we're looking at more like
six months.
So you got to make the spacefor people to do that and it
takes time.
Sophie Buonassisi (35:15):
How did you think about evolving product and
go to market alignment duringthat shift?
Stevie Case (35:21):
Yeah, this was big and it is ongoing.
This will be a forever thing.
At the beginning I felt reallypassionate about this move up
market and so this is a littlebit of a I would say this is a
little bit of a counterintuitivebet.
(35:43):
I went go to market first atmarket.
This is kind of ill-advised.
This is actually not the adviceI would give most people, but I
felt really passionate about it.
I thought there was somethingthere and I thought I can build
a team and make the math suchthat I can send the team after
this opportunity and we canlearn what the market looks like
and we can use that to thenbring data back to the rest of
(36:07):
the organization and show theproduct team what we think we
need to really win up there.
So you know, in mostorganizations you want to go
product first if you're going tomake this move.
We did go the other way.
We went go-to-market first.
So what we did is we createdthis product feedback loop and
we really doubled down on salesengineering for the first time,
(36:28):
which was not a big functionback then for us, but brought in
our SEs and we started todevelop a point of view on what
is the product and what does itneed to be for us to win really
in the mid-market at that point?
For us to win really in the midmarket at that point, we had
frequent sort of voice ofcustomer meetings with products
(36:48):
and we were bringing them reallythe intelligence on who is this
buyer, what software do theyuse today, what are their needs?
And you know, little feature bylittle feature, we were just
asking them to sort of likebuild this future vision and at
that point we were not, as acompany, yet committed to that
(37:09):
upmarket product.
So it was, it was slow andplotting, and we were getting,
you know, we were beg, borrowand stealing like resources, and
convincing people to ship thislittle feature here, this little
feature.
And you know we made progressagainst it and we were able to
then go back and show like, oh,that really landed.
And we were starting to do allthe things you do like prove
(37:32):
that you've got a certain numberof pipeline dollars against a
certain feature request andstack ranking those.
And you know it was just a lotof conversation.
And at a certain point when wegot enough traction and we felt
like the product was thensufficient to meet this like
larger buyer need.
Then we actually had a formalconversation as a leadership
(37:53):
team and this was fun because Iworked on this with Chase Lee,
who came into Vanta as a VPproduct.
He was the CEO founder of acompany called Trustpage that we
had acquired.
So Chase was superentrepreneurial and he was
seeing the same marketopportunity as a VP product.
He was the CEO founder of acompany called TrustPage that we
had acquired.
So Chase was superentrepreneurial and he was
seeing the same upmarketopportunity and so he was on the
(38:15):
EPD side of the house and so Ikind of like he became my ally
in this and he and I made thecase we brought this to the
leadership team that we shouldmake a real material investment
in the millions of dollars, innot just go-to-market for
upmarket, but also in theproduct.
And we ended up greenlightingthat investment and that was
sort of the formal start.
But that didn't happen until agood year after I had put this
(38:38):
little go-to-market squad ongoing to prove the theory.
So it was a long journey to getthere, but then we had our
proof points and once that wasgreenlit then we really clicked
into.
Okay, we now have a businesswhere we're building two
separate things and, granted,it's one product, but the
product experience for a startupfounder is very different than
the product experience for, like, a CISO who's our upmarket
(38:59):
buyer.
So then we were starting tobuild different engines in the
business to take us after thosedifferent opportunities.
Sophie Buonassisi (39:10):
Why would you advise founders not to do that
and go product first instead ofgo to market first?
Stevie Case (39:16):
You have to be really sure.
It's really easy to getdistracted, especially by
inbound lead flow.
And this is a common thingbecause, honestly, every founder
what they should be focused onis getting product market fit
and then scaling that one thingthey do really well.
The failure mode for a lot offounders is like shiny thing
(39:38):
syndrome, where it's like we'redoing this one thing really
really well, but then, oh,there's this huge enterprise and
they said, if we do xyz and webuild these features for them,
they'll pay us a million bucksand like, oh, that would be a
big deal for us.
And then you get sucked intothat and then you kind of don't
account for the fact thatthere's like a huge amount of
support required and it canreally derail you from your core
(40:00):
mission.
So so I advise founders to goproduct first, because if you
try to force something like thatwith go to market, you can
completely randomize yourproduct development and you can
really take yourself off courseand end up slowing everything
down and kind of kill theproduct market fit of the thing
you had that was working in thefirst place.
(40:21):
So if you're going to go aftera new segment, you need to be
really, really sure there'ssomething there and that was for
me that, like the sign that itthat it was a bet worth making
at the time I did is one I hadhigh confidence in myself and my
own analysis and I deeplybelieved I saw something real.
(40:44):
You know, I had seen at Twiliothat journey from just serving
small companies to serving largeLike.
I joined as an enterprise AE atTwilio and they didn't have an
establishment of the enterprisesegment when I started we were
about 200 million in revenuethere and we only had enterprise
customers that were like bigtech scale-ups, so like Amazon,
(41:06):
netflix, these kind of companies, and we had a few but not a ton
.
When I left six years later,the enterprise business was a $1
billion run rate business and,like in my first couple of years
, I personally landed dozens ofFortune 500 logos there.
So I had seen that journey andI saw what it looked like at the
beginning.
(41:27):
When it you know, my firstFortune 500 deal, which at
Twilio was a $500 deal, like, Isaw that journey up to like $10
million deals and a billiondollar run rate.
So I knew what it looked likeand smelled like and I felt,
like at Vanta, I smelled it likeit was there and I could see
that there was something real.
So I was making a bet that Icould make the math work by
(41:53):
pursuing this like tip of thespear strategy with go to market
, going up market, because Ibelieved there was something
very real there.
And I also knew, like you know,it's a bet, it's an experiment.
If it doesn't work out, we canrecalibrate.
I wasn't confident enough atthe beginning to say like, let's
make that multi-million dollarinvestment on day one.
That's kind of why I went to goprove it out.
(42:14):
We sent this squad out to proveit out and luckily, what they
found was it was real and wewere able to capitalize on it.
Sophie Buonassisi (42:21):
And you probably wouldn't have had that
really high conviction if youhadn't worn those shoes at
Twilio and had that experiencefirsthand.
Stevie Case (42:28):
Yeah, exactly Because I had the confidence to
know what a successful, scalableenterprise business looks like
and I had seen the journey toget there and like what it
looked like on day one and thenwhat it looked like several
years later.
So because I had seen that andI knew how the math worked and I
knew how to increase deal size.
There's some very like, there'ssome mechanics in there of how
(42:49):
you can build a package forenterprises from something that
started as a small SMB product.
So you're right, I had theconfidence of having seen that
journey and I believed I couldreplicate it.
So and it's interesting inretrospect because you know
Christina hiring me in the CROrole most of my experience had
been enterprise, at least in themost recent years.
(43:11):
So she kind of brought me intothis very down market business.
I know her thesis at the timeis she wanted somebody that had
seen both, that had seen small,like developers and SMBs, and
somebody who had seen enterprise.
So I think that that ended uppaying off.
Sophie Buonassisi (43:29):
And it all comes full circle that moment
when you're questioning did theymake the right decision to?
Yes, they absolutely made theright decision.
Stevie Case (43:37):
Hopefully I've proven that out by now.
I do.
I definitely am coming from aplace of higher confidence at
this point, Like, yeah, it liketakes a while as a CRO.
This is the funny thing abouttaking your first CRO gig is
everybody's got advice.
Nobody really understands whatyou're dealing with.
You know, I remember at the verybeginning, actually, the first
(43:57):
person that the Sequoia teamconnected me with was Shant,
who's the CRO at Figma, and Iwas like, tell me what to do,
what is the job?
Where should I start?
And he had advice.
But he's like every business isso different and that's what
you come to realize is there'snot a playbook, you have to
(44:20):
build it for yourself and everyis so unique and it's a super
sink or swim job.
So like you can get theselittle nuggets of advice from
people but nobody can reallytell you how to do the job.
You got to figure it out.
Most CROs like 18 months isconsidered success in the CRO
role.
So I'm three and a half yearsin feeling good like I survived
(44:41):
to tell the tale.
But man, it's hard.
So you got to figure out how toget your hands on those gears
and on the levers and if you canfigure out how to make numbers
move.
That is really, at the end ofthe day, the job, and that
sounds really simple.
But trying to figure out how tomove metrics is actually quite
hard when you're.
The levers you've got are likedozens to hundreds of people and
(45:04):
you've got all these differentdynamics.
So I feel very lucky and andhere we are several years later
and we're having a blast.
Sophie Buonassisi (45:13):
And we're north of 100 million.
Were there any other pivotal goto market shifts along the
journey to get there that maybewe haven't covered?
Oh my?
Stevie Case (45:20):
gosh.
Yeah, I mean, the biggest ofthose, when I look back, was
actually not pre-sales, so had awhole journey there, you know,
getting new logo revenue goingup into the right.
But the next big inflection wasactually post-sales and you
know we had a very down marketbusiness.
As you can imagine, we sell tofounders and you know those like
(45:41):
net retention when you sell tostartups is naturally going to
gravitate lower.
If you just look at averagesacross the industry, you know
companies who sell to SMBs aretypically hovering around 100%
net retention, whereas if you'reselling to enterprises to 120,
140.
And as you get to biggerrevenue targets and the law of
(46:02):
big numbers becomes real, netretention has to go up.
So that was my second sort of18-month journey was figuring
out how to get my hands on thelevers in post-sales and drive
gross retention up, butespecially drive net retention
up.
We had no real expansion motion.
(46:23):
When I started we took on acustomer success team.
It was a big team.
They were being asked to doeverything renewals, expansion,
customer education and healthadoption, like everything and it
was totally set up for them tofail because their job was like
a hundred different things andyou can't succeed when your job
is a hundred different things,and so there was this journey to
(46:46):
redefine that team.
We broke it into two piecescustomer success and account
management.
That's evolved.
So customer success now ownsgross retention, account
management owns renewal andexpansion.
I hired an incredible leader inthere, kelly Bray, who leads
all things post sales for me,who is just crushing it.
And similarly, it took abouttwo years.
(47:08):
We had to build a sales enginein post sales and you know that
has been wild and we've moved,you know net retention of double
digit numbers and that was noteasy.
And it's another one wherethere's no playbook.
Everybody does post sales verydifferently.
(47:29):
It's even less standardizedthan sales.
So huge learnings in there, andI've been so grateful to have
Kelly as a partner in it and Ithink we're doing some really
kind of groundbreaking stuff inpost sales today, like where you
got to.
It's one of those unique thingstoo, because it's not just
selling stuff You've got,there's the entire customer
experience You've got to.
You know, ensure customersadopt the platform, that they're
(47:51):
satisfied, that they have agreat quality experience, and
then you want to tell them moreabout the rest of the platform
and and get them to adopt evenmore of what Vance has built,
cause we built a lot of productsover the last year.
You know we aren't just nowkind of that core compliance use
case.
We do vendor risk, we docustomer trust, we do
questionnaire automation.
You know we've got this wholesuite of products so that
(48:15):
post-sales team have to be trueexperts on the platform, as they
are also serving our customers.
So big journey there as welland a lot of learning.
That was a new one for me.
Sophie Buonassisi (48:25):
What approximate year was that, would
you say?
Stevie Case (48:28):
I took that on initially about nine months into
my tenure to start and you knowI would say the first six
months I was really just gettingmy hands around like how does
this even work?
Like how is this team workingtoday?
Like what are the basics here?
Going out and I do anytime Itake on something new I go out
(48:49):
and talk to as many people as Ican, so talking to tons of
customer success leaders andaccount management leaders, just
talking to anybody I can talkto to understand how they do it.
So it's about six months ofinvestigation.
Then we started transformationand you know the first
transformation was that breakingthe team into customer success
(49:09):
and account management, so twodifferent functions and that
first change was about 12 monthsafter I took on the team and
then from there that was a goodyou know.
So it's been, you know, acouple of years since we made
that change and there's been alot of incremental change since
then.
So we're about two years intothe journey and we it took about
(49:30):
a year and a half to really seethat start to pay big dividends
.
Sophie Buonassisi (49:36):
We're hearing the pattern of starting
initiatives and really waitingand having the patience to see
it pay off, as opposed to theimmediacy.
Yeah, so time, yeah, yeah.
And Steve, you now, I meanyou're north of 100 million ARR
and Series D.
Congrats again.
What's the next biggo-to-market focus for you and
where are the opportunitiesahead?
Stevie Case (49:57):
Yeah, I've got a couple of big ones over this
coming year.
So one is really sell theplatform and what that means for
us is just like when I arrivedand we kind of had one sales
team and no segments.
We now have multiple segments,this broad team, but that broad
team is really selling the coreplatform.
The reality is we have shippeda lot of other incredible
(50:20):
products.
This vendor risk product that'sbecoming a true third-party
risk product.
Our entire customer trustplatform.
We've got these other elementsin the platform.
We've got an access reviewproduct.
They can in many cases be soldstandalone.
So now a lot of the mission islet's go sell those as true
(50:41):
standalone products to differentbuyer personas and it means
really creating separate teamsand muscles and motions in our
go-to-market engine.
So that's a big one.
That's a huge area ofinvestment.
We've got killer products inthese areas.
But again, like the productsdon't sort of like figure out
how to sell themselves.
(51:01):
You've got to go figure out howto build a funnel for each one,
how do you identify buyers, andthen you've got to create the
space for a team to actually gosell that and not it's
counterintuitive, but like notget weighed down by the success
of the core product.
So if you give everybody youknow the whole platform to sell,
they're going to sell the corething that sells.
Well, they won't pay attentionto, like the products that are
(51:21):
emerging.
So you got to create space forsomebody to focus on just
emerging products.
So that's the one big one.
The next big one is really goingto be what we're calling Vanta
for government public sector.
We just went down this path andjust last week got our FedRAMP
20X low authorization, which isa big deal.
(51:44):
It's like the federalgovernment is doing this pilot
program to essentially expeditepeople being able to be fedramp
compliant, which now allows themnot just to sell to the federal
government but in our case itmakes it so we can help other
companies become fedrampcompliant.
So they're sort of like sellingto the government and then
they're selling to othercompanies who sell to the
government as well.
(52:05):
Massive opportunity for us.
We're really excited about itand we are committed to that
journey to really work in thatfederal ecosystem.
So, building out a publicsector function, bringing in
leadership there and doublingdown on our opportunity there is
another big area.
And doubling down on ouropportunity, there is another
big area.
And then the third is thecontinuation of the journey
(52:25):
we're on, which is servinglarger and larger enterprises.
So we do serve today atremendous number of large
enterprises.
We've got customers in theFortune 100.
We are selling to not just techscale-ups but like true kind of
old school enterprise logos,and so continuing down that path
and serving their needs aroundgovernance, risk and compliance
(52:48):
is going to be a big part of themission over the next year.
Sophie Buonassisi (52:52):
Incredible Well excited to see all of that
in execution.
And, stevie, I've got to askyou how are you using AI
personally and in Vanta andlearning about AI?
How are you?
Stevie Case (53:04):
using AI personally and in Vanta and learning about
AI.
Yeah, we've got a couple of bigangles here.
So I am a big believer in AI.
I am very bullish and, honestly, like what we're doing at the
heart of it is sort of remakingthe way we think about revenue
operations.
So historically, revenueoperations teams were more
system admins, not necessarilybuilders and folks who wrote
(53:26):
code.
We are moving in the directionof building an AI builder
function within revenueoperations.
We've already got a teamstarted there.
So we are infusing AI intobasically every workflow every
workflow.
So all of the basic things youwould think of like updating CRM
with AI, delivering pre-callprep notes to our teams with AI
(53:52):
all of those workflows now exist.
Now we're starting to thinkabout some next stage use cases,
like we're bringing in anagentic platform to help bring
customers through onboarding ina really interesting way.
We've, of course, infused it insupport, where we can really
shorten response times and getgreat high quality responses.
So like we're building iteverywhere At the same time, we
(54:15):
are making a bet on humans.
So I look at AI and go tomarket as an opportunity to
allow our humans to do thehigher value work and really up
level the way they function.
So big investment on both thetech and humans.
Personally, I am having a blastwith it.
I love it.
I ended up buying an entirelynew laptop so I could experiment
(54:36):
and just sort of go wild.
Sophie Buonassisi (54:38):
I love it.
Stevie Case (54:40):
Oh yeah, I'm actually building an app right
now.
I've been playing around withboth Cursor and Replit and
having a ton of fun with that.
I'm, of course, obsessed withChatGPT and use it for basically
everything in my life foreverything from fun things and
(55:06):
sort of entertainment tointerpreting my lab work when I
can't get ahold of my doctor to.
I actually did my taxes thisyear with the help of chat GPT.
Highly recommend TurboTax pluschat GPT magical combination
totally worked for me.
So you know, I I'm a believer.
I know there are a lot ofskeptics and they'll say, like
you know that you should not,but I don't know.
I've had a great experience andI'm bullish.
(55:29):
I think that you know.
Ai gives us the opportunity todo things that are more human
and can take out that minutiae,and I'm enjoying it.
Sophie Buonassisi (55:41):
What about the other side of the coin from
AI?
Are there any books that you'veparticularly enjoyed and that
you'd recommend to anyonelistening?
Stevie Case (55:49):
Yeah, it's a great question.
So right now I am reading abook called Endurance, not a
business book but kind of aleadership book.
You know it's great.
It's about this shipwreck andkind of the way that this crew
led themselves out of this verydire situation where they were
shipwrecked in, of the way thatthis crew led themselves out of
this very dire situation wherethey were shipwrecked in a very
bad situation Book that wasgiven to me by Varun, the COO
(56:13):
and founder over at Clay Greatcrew.
So that's what I'm enjoyingright now.
I do a lot of business books aswell, as you can imagine.
So it's kind of nice to get alittle respite from the business
books.
And there, you know, you got todo all the classics, the like.
You know the, the Slootmanbooks, you know the qualified
(56:33):
revenue leader, always a fan ofthe classic challenger sale,
like I still think that lands.
I still go back to thatstructure.
So, yeah, all all of those aregreat, but I'm trying to take a
break it's summer and readsomething a little more off the
beaten path.
Sophie Buonassisi (56:50):
Yeah, yeah, fair enough.
And where can people find youif they want to get in touch or
follow your journey?
Stevie Case (56:57):
Yeah, they can find me on LinkedIn, so I am posting
on LinkedIn super active, loveto connect there, so come find
me Awesome.
Sophie Buonassisi (57:05):
We'll pop it into the show notes, Stevie.
Thank you so much for joining.
Congratulations again on theSeries D, and we can't wait to
see the continuing progress thatyou and Benta have.
Stevie Case (57:13):
Thank you so much.
It's been great being here.
Sophie Buonassisi (57:16):
Awesome To everyone listening.
Thank you for joining us andwe'll see you next week.
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