Revenue Culture That Survives the Boom/Jeff Perry - Carta, Cap Tables, Private Capital ~ Spark of Ages Ep 49 - Spark of Ages

Episode Transcript
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Jeff Perry (00:00):
The landscape is totally different now.
I mean, back then, companieswere on a chase to get to 100
million ARR, and that meant ifyou do that, you can IPO.
And now we're in a totallydifferent world now.
And so, like, what is a IPOready company?
And then more importantly, whatis a IPO ready and can be
successful beyond that is themore important thread to pull
there, too.

Rajiv Parikh (00:24):
Welcome to the Spark of Ages podcast.
Today we're joined by JeffPerry, the Chief Revenue Officer
at Carta, whose journey fromprocessing paper stock
certificates in the most analogway possible to leading one of
the fintech's biggesthyper-growth stories.
It's an absolute wild, wildstory.
Jeff is a proven revenuesuperstar whose career journey

(00:47):
spans decades across largeenterprise software giants like
Oracle and high-growth staffstartups like Docus.
He is recognized as an iconicrevenue leader who knows how to
build sophisticated revenuemachines that scale with
purpose.
Under his leadership as CRO atCarta, Jeff has orchestrated a
phase of intense hypergrowth,scaling Carta's annual recurring

(01:09):
revenue from approximately $20million ARR to a remarkable $450
million ARR.
That's a 22X increase whilemanaging everything from new
business and upsell to customersuccess across Carta's multiple
business lines.
Jeff attended Santa ClaraUniversity where he received a
BS in political science andwhere he also played NCAA

(01:30):
baseball.
And you can see that teammentality and how he leads.
Focus on maximizing yourcurrent role, master your craft,
and the opportunities willcome.
Some of the key takeaways youcan expect from this episode.
How Carta is monetizing itsbellware status as it further
drives into enterprise sales.
What the new definition of fastgrowth is for startups ahead in

(01:54):
2026.
And finally, why Jeff valuesperformance under pressure and
those who operate from a fear offailure.
Jeff, welcome to the Spark ofAges.

Jeff Perry (02:03):
Rajiv, uh pleasure to be with you.
Thank you for having me.
Look forward to the discussiontoday.

So, Jeff, it was so great to meet you at the Go
to Market Leadership Societyevent.
You were speaking there aboutthe CRO and CFO relationship,
and I love the story.
Of course, I'm a fan of Carta.
My company uses the software,and it's you know, as an
entrepreneur, it hits one of theproblems I deal with, which is
dealing with cap tables and allthe misery around.
So great to have you on.

Jeff Perry (02:26):
Well, thank you for being a user.
We have you know thousands,millions of fans, Carta fans out
there now.
Everyone loves getting theirsting email with confetti,
letting them know they have uhnew vested shares.
So we take the same enjoymentand excitement with all of our
customers, too.

That's right.
So just let everyone know,Carta is a leading equity
management platform that helpsstartups, private companies,
investors, and employees trackand manage ownership, stock
options, and fundraising withease.
So the platform digitizes andautomates the complexities of
equity management, such as cattable calculations, which is the
biggest pain in the butt,regulatory compliance, an even
bigger pain in the butt,employee stock plans and

(03:00):
valuations, giving allstakeholders real-time
transparency and a streamlinedexperience.
So if you are running acompany, this is something you
deal with.
And that's how you guys made aname for yourself, right?
Was in that initial pain.

Jeff Perry (03:12):
It definitely is, yeah.
I actually was reminded byHenry, our CEO, uh, last week in
a discussion.
The original problem statementto solve was actually reducing
or eliminating the shipping costof sending an actual stock
certificate to an employee or aninvestor.
So it was literally trying tolike save the cost of UPS or
FedEx bills to ship the actualcertificate.

(03:32):
But what WCARTA really hasbecome is taking a spreadsheet
problem or a service problem andputting into software and into
the cloud.
Uh and we've done that, youknow, that's how CARDA got
started on the cap table sidewith stock certificates and then
became 409A valuations.
And then we've also done thesame problem solving on the fund
administration side for VC andPE firms, where you have a
spreadsheet or accountingpractice in a service model.

(03:54):
And we've taken that and putthat into software and in the
cloud as well.
And so we built our fundadministration general ledger
that now serves 2,500 plus uh VCand PE firms too.

That's where the real revenue is, right?
I mean, that's not where youstarted, but that's what's
become the main source ofrevenue for the for the company,
growth for.

Jeff Perry (04:12):
That's right.
Yeah.
The cap table business is stillroughly two-thirds uh of the
revenue.
But as the other businesseshave been growing, you know, we
we internally joke that at somepoint the captable business
becomes the side hustle forCarta and it's the connectivity
of stakeholders and founderswith investors.
But over time, you know, thethe larger opportunities and the
future of new products that wecontinue to add will be around

(04:33):
the fund administration platformand this concept of an ERP for
the office of a private capitalCFO.
And that's what we're buildingtowards.
So captable will always be apart of it.
It's on the front end of theERP.
But the reality is the biggeropportunity is to continue to do
fund administration andadditional products around that
to help serve the office of theCFO.

In a way, it's how people get to know you through
a captable product, right?
It definitely is.

Jeff Perry (04:55):
Yeah.
I mean, most people know ofCARTA as you know, originally
eShares because, you know,whether they were an employee or
an investor of some kind,received a CARTA account and
received some shares and equity.
That is evolving and changinginto that's something that we do
and will always do and do verywell.
But we continue to expand whowe work with and broaden that
network.
You know, we did an acquisitionabout two weeks ago, uh company

(05:16):
called Excelix, which werebasically helping extract very
complex fragmented data pointsof LPs and pull that into one
seamless report for them.
So we're working with foundersand captables, CFOs for venture
capital and private equityfirms, and now the LP community
as well.

That's great.
So it's you're you're buildingoff that network base, right?
As you have thisinterconnection.
So Carter CEO Henry Ward, asyou mentioned earlier, has noted
that founders often make themistake of spending heavily on
sales too soon, which can maskbad product market fit.
So when you were reorientingyour revenue teams after the
2021 boom and facing potentiallyvolatile macro environment, how

(05:54):
did you decide what wasnecessary go-to-market expense
versus an expense that mighthide underlying friction?
And what non-revenue metric waskey to ensuring your sales reps
were focused on must-have valuerather than just closing deals?

Jeff Perry (06:08):
Yeah, it's such a great question.
You know, and you know, whetherit's CARTA or any of the stops
I've been along the way, there'sthis old adage of like, if you
just add more capacity, thenthat will equate to more
revenue.
And we subscribed to thatmethodology in my first couple
of years here because there wasproduct market fit and the
inbound flow was wassignificantly high.
Reality is like there's only somany companies being created
and only so many companies beingfunded, which are the

(06:31):
time-bound opportunities forthem to consider a captable
solution.
So there's not a lot I can doto help influence that aside
from the network effect that wehave with law firms and venture
capital firms.
So we had to change sort of howwe think about the business.
And it's not just to add morecapacity equates to more
revenue.
It's how do you get moreefficient?
How do you get smarter?
How do you leverage some of thedifferent avenues to source
inbound?

(06:51):
And so we started workingobviously with incubators and
accelerators.
We deepened the breadth of thelong tail of law firms that we
work with to solidify thatpartnership.
And so, you know, it's classicCarta, like we adapt, we evolve.
So as we're doing that, we'rebuilding the fund admin product,
we're adding products to that.
A perfect example is like, youknow, we found that there was a
problem with distributing K1s ina timely manner.

(07:12):
So we said, you know what, wehave all the information inside
of our platform as is.
Why don't we create a K1product and do taxes for our
firms?
And so for us and the team,that's great.
It allows an upsell, cross-sellopportunity to existing
customers.
It allows us to add somethingnew to new business customers as
well, as far as the completeoffering that we have.
And that allows us to expandrevenue.

(07:33):
And like it's one of the thingsI love about Carta is we're
constantly looking at sort ofthe three main businesses of
companies, cap tables, venturecapital, and private equity, and
then figuring out whatadditional products we can add
to the offering to add morevalue to our end user customer.

When you got into that situation of like, so
things are flying in 2021.
And after that, the market kindof tipped, right?
For startups, funding fell,especially with software
companies.
They were exploding and theywere getting amazing valuations,
and it kind of cut it all.
Everyone, you know, there was abig drop in it.
So did you have to cutgo-to-market expense, or was
this where the new productsenabled you to supersede that

(08:09):
situation?

Jeff Perry (08:09):
So a little of both, right?
So we went through COVID wherewe did a reduction and then we
started to build the sales teamback up.
And then you realize, like,wow, we can do this maybe a
little bit leaner than we haddone before, and how efficient
can we get in the model?
At that point, I think we hadum sort of an overlay team
selling our total compensationproduct because we experimented.
We thought specialization forthat product would be the best
way to take it to market as faras the sales organization

(08:32):
structure.
After probably two and a halfquarters or so, we learned that
like we can actually have thesame account executive sell all
the products that we offer to anewbound customer base.
And so we got more efficient inthe number of headcount that we
needed and more efficient inoverall resource spend to make
sure that we're optimized forthe customer experience.
And then also think about theinvestment businesses that we're

(08:54):
building simultaneously thatbecome the future growth and the
future cap table businesses forus along the way.

That's really interesting.

Jeff Perry (09:00):
You know, and you mentioned uh, you know, a metric
that's sort of outside ofrevenue to measure.
One of the things that we'vebeen watching closely over the
last several quarters is just aproductivity metric around
number of meetings had or numberof chorus calls we have, Zoom
calls by AE per month.
And sometimes it's not the bestindicator.
Other times it's very clear oflike productivity.

(09:21):
Obviously, like the folks thatare exceeding quotas and getting
into accelerators and making alot of money are the ones that
have more meetings.
And so, like, that hasn'tchanged in the 20 plus years
I've been doing sales at Oracle,DockySign, and Carta.
The busier you are, the morecustomers you're talking to, the
more opportunities you have tosell and be more successful.
And that formula hasn'tchanged.

(09:41):
So we're watching thoseactivity metrics too.

That's your leading indicator.
Like, if you're it is you know,because by the time you get to
the end of a cycle, your time tomake a change is you know,
you're getting stuff way, waylater.
So this is your leadingindicator.

Jeff Perry (09:52):
It is, yeah, because you can track the traditional
like number of calls, number ofemails, but frankly, like
everyone is doing that.
And the the sophistication ofthe buyer has changed with like
the introduction of AI and allthe information that people can
gather prior to getting on acall with with Carta, the
customer is prepared.
And so doing a cold call mightnot necessarily be the best way

(10:13):
to connect with them, but makingsure that you're doing all the
things that are within yourcontrol to get as many meetings
as you can to make sure yourcalendar is as populated as it
can possibly be to give you thebest chance to be successful.

That's great.
So are you finding the dataindicates nowadays that like you
were saying, people find youbefore you find them, right?
As uh more Gen Z folks arebuyers, they're even more so
than Gen X folks, right?
And then are you finding thatAI is helping you with that as
well?
Like, are they educatingthemselves with AI or using AI
tools, or maybe it's both?

Jeff Perry (10:43):
It's a combination, not to dodge the question, but
it's always a little bit ofsomewhere in between, right?
And uh typical with Carta, Ican't always answer one question
with just the simple answerbecause the three businesses are
very unique.
They're at different stages ofmaturity as well.
So, as far as like captableinformation and it being readily
available, yes, it's a newergeneration of founders typically
on the forefront of cuttingedge technology.

(11:04):
And so they've done theirresearch.
They typically are working witha law firm or a VC firm that
has hopefully recommended CARDAto them as well.
Typically, they've worked withCARDA before.
So, from a captable standpoint,you're getting a warmer lead or
an introduction with someonethat is actually understanding
CARTA to and what we do.
That's also coming true in theventure capital business for

(11:24):
fund administration.
In private equity, we've spenta lot of time over the last year
and a half in educating amarket of what CARTA's offering
is.
And so you sort of meet peoplewhere they're at with their
familiarity with Carta and whatwe offer.
And I would say almost 100% ofthe time, people that we talk
with, it doesn't matter if it'sa founder of a cat table
business or a CFO of a privateequity firm, they don't fully

(11:46):
understand the full breadth ofeverything that Carta does and
offers.
So it's an opportunity for usto be a trusted advisor, educate
a prospect on all the thingsthat we have to offer and add
ultimately add value for them.

So now CARDA successfully utilized a velocity
model to win early stagefounders and emerging fund
managers.
However, the current marketdemands a focus on capital
efficiency.
As you know, growth rates havegenerally declined across the
SaaS industry in 2024 and 2025.
And not sure if you're seeingthat as well on your side, but
how did the CRO organizationpivot its primary efficiency

(12:19):
focus from optimizing customeracquisition cost or CAC payback
based on a high volume startupdeals towards demonstrating
long-term growth endurancewithin the nascent high value
private equity segment where alot of future growth is expected
to originate?

Jeff Perry (12:32):
Yeah, well, you nailed it.
Cardo was started off ofworking with early stage
founders.
And you know, we even created alaunch product, which is free
for founders that have raisedless than a million dollars or
have less than 25 stakeholderson their cap table.
So we offer that at no costbecause the idea is we get them
on the platform early.
If they grow and they're asuccessful company, they'll
convert to a paid plan at somepoint.
And we want to kind of meetthem where they are in their

(12:54):
journey of growth, help advisethem along the way, have you
know a decade plus longrelationship with them on their
journey to potentially IPO, andwe can do all the things for
them along the way.
We took the same formula withwinning early stage venture
firms when we started this backin 2018-19.
We didn't go after the largestfirms in the world that were
hundreds of billions of dollarsof AUM.

(13:15):
We started with first-time fundmanagers and emerging managers
and made sure we won thatmarket, take that cap table
formula, apply it to what we didin venture.
That's why we have 2,500 plusfirms using the Carta uh
platform now.
Ultimately, though, you'reright.
Like we have far greateraspirations as a company to be
much larger than we are now andto reach those aggressive growth
targets.

(13:35):
You can't do that solely off ofemerging managers or smaller
funds.
And so you naturally, like mostcompanies, go through this
inflection point of I did theSMB thing, now I need to evolve
into mid-market, enterprise, andcross-market as well.
And so for us, it was workingwith larger, more established
firms, which we're doing now andhave been for the last several
years, and then working across-market in making sure that

(13:58):
the offering that we have isalso uh applicable and relevant
to private equity firms too.
So it allowed us to move up andover to continue to earn higher
ACVs that help us achieve thehigher growth targets that we're
we're looking to do as athriving business.

Yeah.
So did you end up getting adifferent kind of Salesforce or
is it the same Salesforce?
And then I'm sure yourmarketing changed as well for
it.

Jeff Perry (14:17):
All of the above, yes.
Different Salesforce.
The profile of an accountexecutive for our captable
business is an SMB type profile,very different than an
individual that we bring onboard to work with CFOs of you
know, multi-billion dollarprivate equity or venture
capital firm.
So there just takes a differentexperience set, a different
background set to be able to dothat.
So the profile of the salesorganization has evolved over

(14:39):
the years to where now I feellike we're optimized to be able
to have the right conversationswith the right prospects and
where they're at.

That's great.
So you're borrowing off yourexperience from you know, you're
doing enterprise at Oracle,right?
So it's kind of like me in myearly days.
I was selling computer systemsat Sun Microsystems and at ATP.
So you had the enterprise salethere, then you have the
DocuSign SMB sale.

Jeff Perry (14:59):
Yeah, there's so many things.
I guess you don't realize itwhile you're you're sort of
growing up in your career, butso many lessons learned from my
time at Oracle and DocuSign thatI apply now to, you know, going
from SMB to enterprise or doingcross-sell and upsell motions,
multi-product, customer success.
There's so many things that,you know, I was learning at the
time that I didn't realize wouldbe so valuable and beneficial

(15:19):
in the role that I'm in now.

Just like you're talking about, you have a
simultaneous go-to-marketmotions with high velocity
14-day cap table sales cycles,right?
To 90 plus day enterprise VCfunded administration motions.
So, what do you find to be thesingle biggest organizational
tension point that thisstandardization paradox creates
outside the sales team?
So, like you have RevOps,enablement, marketing, product

(15:42):
teams.
How do you prevent thatinternal friction from
negatively impacting thecustomer experience for your
largest enterprise clients?

Jeff Perry (15:49):
It's not easy, but I would say that you know, the
key to the success of all thisis the transparency and the
relationships that I've createdover seven years now with my
peers as part of the exec team.
And, you know, I work veryclosely with Henry and Charlie,
our CFO, and Nicole, our CMO,and the product team and
Rushali, you know, to make surethat like everyone is an
understanding of where we arefrom a pipeline perspective and

(16:10):
the opportunities that are partof it, and also understanding
that each of those businessesthat I've described, they're at
different maturity levels of thepipeline and the consistency
for which they they perform.
And so, yes, we expect the captable business to move very
quickly and it's veryconsistent.
We have more enterprise-likedeals on the venture capital and
fund admin side and in privateequity that are longer sales

(16:31):
cycled and oftentimes very muchtime bound by a firm either not
having a great experience withthe current provider and or
raising a new fund.
And so I can't always controlthose two time variables.
But what I do need to make sureis that the team is in the best
position to createrelationships over a period of
time for when one of those twothings likely happens, and we're

(16:52):
there to be able to share whatCarter can do to help make a
better experience for them.

This is the kind of stuff I love.
Like you, you know, if you'rein marketing, we are always
looking for that moment thatmatters, like what takes someone
from their current state towanting to switch, right?
So, in many ways, you're not ina nascent market anymore where
they're just you're justeducating them.
In some places, they have othersolutions and now you're trying
to switch them over.
So, like, how's thatinteraction with marketing where

(17:17):
they're helping you find thatintent, the intent of that
person to switch, and thenturning you on to it?
Or you're probably looking atit together, right?
You probably look at yourcalls, you're probably looking
at we review everythingtogether, which is wonderful.

Jeff Perry (17:29):
I uh, you know, I feel very fortunate that I have
a great partnership with ourCMO, Nicole Bayer, and her team
because we look at thistogether.
And it and from our mindset,it's a shared number.
It's not just Jeff's revenuenumber, it's our collective
number to hit together.
But again, the businesses areat different stages.
So typically, uh, you know, acap table lead will come in and
the current incumbent is like donothing or doing it in a

(17:49):
spreadsheet.
So there's an opportunity forus to insert like what Carta
does and how we make that moreefficient for the founder.
Very different than like thewarming of a lead and the
educating of a prospect inventure fund admin or private
equity that creates that longersales cycle.
We've also, you know, there'sSF Tech Week has just happened,
LA Tech Week.
We try and leverage some ofthese broader events to do some

(18:11):
of our own, what I would callmore curated specific events for
Carta customers and prospects.
And we've been doing a lot ofthat in the last couple of weeks
here, bringing togethercustomers that we know have had
a great experience once they'vemoved from another provider to
Carta and have them help sharetheir story about their
experience and why it'sdifferent and better since
they've started working with us.
And there's no one better tosell your product than an

(18:33):
existing customer to a prospect.
Like so them hearing like thetruth and the accuracy of their
experience has been really,really helpful.
Those things don't happenwithout the support of the
marketing team that we've we'venow have in place.
That's interesting.

In one of our previous podcasts, you know, we
were talking about these, youknow, the B2B marketing
practices.
What folks are talking abouttoday is that many of the
digital metrics that we're usingbefore, many of the digital
methods we're using to reachfolks have become a bit
saturated, or you need you knowyou've hit a point of
optimization.
So now intimate events areactually more valuable than they

(19:06):
used to be.
Are you finding the same kindof thing?

Jeff Perry (19:08):
Or without a doubt.
Uh just got back from an uhintimate event that we did last
week with all it 10 customersand 15 prospects.
And we brought in the majorityof the C-suite, you know,
product, marketing, sales, totalk about how we work with
customers.
We actually, which was Ithought brilliant, was we did
breakout sessions and actuallylike work through some vignettes
of scenarios that we think aCFO might go through in

(19:30):
reporting and ask them to likebreak into groups facilitated by
people from Carta to help withthe conversation of like, does
this resonate and what would youwant to see built into our
product?
And this is legitimate.
Like, we take the productfeedback.
And later that evening, I waswith our CPO and she was already
talking to her team aboutbuilding the stuff that we had
heard about just hours beforefrom prospects of what they

(19:51):
would need.
So it's like moving andhappening that fast, and we're
able to be that nimble still,even though we've become a
bigger company, to say this iswhat the market is telling us is
needed from prospects.
Let's go build into the productfor them, which is phenomenal.

When you get that kind of cycle time, that's just
incredible.

Jeff Perry (20:07):
It's incredible, yeah.
But you know, this is alsolike, you know, Rashali's also
been at Carta for I think nineyears now.
I've been seven plus.
So we we have a cadence ofworking together and
understanding, like, we'rehearing this, we need your help,
and we need involvement fromthe entire team.
This isn't just a sales thingto get you know revenue over the
line.

That's great.
So you've also at Carta made asubstantial strategic move into
private credit.
Given the general marketsentiment that direct lending
and private credit offersattractive yields and are set to
grow.
What specific market saturationor operational thresholds do
you anticipate private credithitting by the end of 2026?
And how will that influence theCRO organization and
go-to-market resource allocationbetween VC, private equity,

(20:47):
private credit verticals?

Jeff Perry (20:48):
For us, it just became a no-brainer once we
started working with all thesePE firms and understanding that
they have a credit arm as well.
And so we've started workingwith many firms, doing the fund
administration for the firm andthen also servicing the credit
loan component of it.
We were doing that through apartnership uh that we had with
another provider.
Just last week, we announced anacquisition of Cervatis, the
company that will now be part ofCarta, that will help us

(21:10):
service these loans as well.
So, from a resource standpoint,like we're putting our money
and resource behind making thisa great experience for private
equity firms that come to Cartafor both fund admin and for loan
servicing.
Now we have the software andthe services to be able to do
that to answer the go-to-marketpiece.
As I'm doing that, I'm alsobuilding out the sales team and
the marketing functions withNicole's help to make sure that

(21:31):
we're prepared to go capturethis market because we do
believe it becomes the biggestopportunity for us, especially
over the next three years.

That's amazing.

Jeff Perry (21:39):
We're really excited about it.
Yeah, just in the last twoweeks, we've done two
acquisitions, Celex andCervatis.
So all things helping, youknow, the LP community and loan
servicing.
So all the things that we'rebanking on for the future and
the growth of the company, we'rewe're doubling down and leaning
into.

That's amazing.
And so you're not necessarilypulling from one to the next,
you're just taking the growthand you're channeling what
should be next.

Jeff Perry (22:00):
Yes, we believe so.
It's like find the signal inthe market and then figure out
what do we build to go make itbetter.
And then are there things thatwe can buy to help supplement
our offering to?
That's great.

So we're gonna get into a little bit more about
like what you see now.
You have such a breadth of datathat you're seeing from
multiple places in the wholeinvestor venture, now private
equity ecosystem.
So at CARTA, you're trackingessential metrics for your
customers, like ARR per dollarof capital raised, right?
Capital efficiency to increaseproductivity, right?
It's one of the cool partsabout your product.
And however, in the AI, withthe AI revolution, there's uh

(22:32):
massive non-traditionalinfrastructure investment energy
consumption, custom silicon toreduce dependence on
hyperscalers.
So, as the CRO, do you observethe financial models of AI
native private companies whichCarter serves as shifting?
Do you see that shifting?
Is there a requirement forheavy infrastructure investment
leading to like a bifurcation ofcapital efficiency metrics?
So different, you're initiatingapplication layer SaaS startups

(22:55):
from true AI native deep techcompanies that bear high compute
costs.
So are you seeing that in someof the data that you see?

Jeff Perry (23:02):
Yeah, we do.
If you haven't or don't followPeter Walker, he's our our data
analytics specialist in-househere at Carta.
He is hands down the best asfar as all the information that
we have, taking that data andputting it out into consumable
reporting, both on the cap tablestartup side for founders and
then also on the venture side.
So, you know, what we're seeingis like a bit more time in

(23:24):
rounds right now.
The rounds being raised arelarger, obviously, probably not
sharing any like shocking newsto you, but that's what the data
does, but does show.
We also, you know, if on thecap table side, we're seeing an
influx right now of companiesbeing created.
No surprise, large in part dueto all the AI companies being
created.
How many of those become thenext generational companies?

(23:44):
Time will tell on that.
But you know, we're here tosupport that growth.
There's not a VC firm that Italked to.
I was at dinner last night,have another one tonight with
different firms and founderswhere everyone in these venture
funds is talking about likeinvestment in AI companies and
what you're doing to use AI tobe more efficient and maximize
what you can do.
So all of those things that youhear and feel in the market as

(24:06):
you're out talking to people allresonate true in the data that
we gather from all the companieson the platform too.

Yeah.
So I would think like, sobefore when you were investing,
right, the RD expense was of acertain size, but then a lot of
money for SaaS companies wouldgo into go to market.
But now when you're looking atthese companies that just have
massive compute that they haveto invest in, they're just like
putting so much intoinfrastructure.
So your model is going tochange in terms of you're
putting so much intoinfrastructure, you're probably
putting less into go to market.

(24:33):
And so the whole return onequity model shifts, right?
Because before you didn't haveas many assets, now you have
massive assets.
So I wonder how you see that interms of valuations and how
folks look at things.
Because one dollar here is notone dollar there.
Although right now everythingseems to be rising for AI.

Jeff Perry (24:50):
Yeah, it's interesting.
You know, I had someone mentionto me last night that, you
know, through the use of AI,they've gone from 45 SDRs to 15
SDRs.
And so interesting thought.
Like I'm in a differentposition and stance on that
right now, where to me, usingand leveraging AI is less about
how do you reduce cost and likereduce your headcount.
If anything, it's how do youlearn how to use AI to make

(25:12):
everyone more efficient and makewhat you're doing 10x better
than you already are, not reducecosts.
Now, earlier stage smallercompanies clearly looking to be
more cost efficient.
And so do you spend a dollarless there, put that dollar into
RD instead, and do you maximizein a different way?
I think that to me is justdifference in size and stage of
company and where they're at ongrowth trajectory.

(25:32):
And neither is like a right ora wrong.
It's just where they're at andwhere they need to head.
Yeah, one thing I findinteresting too, the more people
I'm I'm out talking to inmeetings, like everyone kind of
gathers, feeling each other outof like, what are you doing with
AI?
How about you?
And like everyone wants to hearall the ideas.
No one has the like, here's thefull stack of AI tools that,
you know, if you do 150 millionin ARR and you have 300 people

(25:53):
in your company and here's kindof what your organization looks
like, here's the stack that youshould be considering for AI.
No one has those answers yet.
So everyone's kind of phishing,right?

Yeah, it's too uncertain.

Jeff Perry (26:02):
It's too uncertain and it's moving too quickly.

I give my team, I have a 200-person team, and I
give my folks a lot of freereign on the operation side to
go play with a whole bunch oftools, right?
And every quarter when I talkto them, they're using new
tools.

Jeff Perry (26:17):
Yes, yeah.

I'm kind of blown away by that.
They're using new tools.
I did force, not force, but Ipushed the answer on well, we
have to pick one agenticplatform because I want them to
unify what they're getting fromthose tools and turn it into
organization-wide processes.
So there is this whole thing ofthere's uncertainty, but you
got to choose at some pointsomething.

Jeff Perry (26:36):
That's definitely true.
We experience the same thing.
And I, you know, it's one ofthe things I love about Carta.
There's such an entrepreneur uhspirit here that people just
want to go learn and experimentand try different things.
That can also get us intolittle trouble where everyone is
doing all these differentthings.
And so that was starting tohappen with AI in a good way,
people experimenting.
But I love what Henry did andbasically said, like, hey, if

(26:57):
there's something that you wantto use AI, you need to submit a
less than three minute videodemo of what it is, why it's
important, why it'll help us.
And then kind of filtering,deciding, okay, is that
something we should do?
And then if so, is it somethingwe would buy or something we
can just build on our own?
And so it helped us sort oflike streamline a bit of the

(27:18):
chaoticness of okay, all this AIstuff and everyone
experimenting everywhere.

Because you want to get to a point of reuse,
right?
If everybody keeps buildingthese agents to do all kinds of
things, if they're not lookingat it from a reusability point
of view, you'll end up buildingmultiple streams of the same
thing, which is fun and it'sinteresting.
You want to let that play out,but you also want it to come
together and be leverageable.

Jeff Perry (27:38):
So that's right.
And most of my visibility tothings was sort of the the GTM
usage of this.
But then you think about therest of the company, and there's
all these other use cases forit that we're being experimented
with.
But obviously, like, you know,we're embracing it here.
And you know, frankly, there'sso many ways we're benefiting
from it already.
My SDR leader has done aphenomenal job and using some
tools to help us be moreefficient and sort of coverage

(28:00):
models and things like that.
We talked about earlier movingup market, you get more
complicated sales cycles.
Oftentimes, those come withRFPs.
We have some tools now to toleverage populating RFPs through
AI.
We launched our own agent tohelp with performance reviews as
well.
So there's a lot that we'redoing that just wasn't even on
the table six months ago.

I literally can come into a meeting and have the
whole workup on who the personis, what the company's doing,
just a full audit in minutes.
It's amazing.
So let me ask you about sowe've seen, as we know, this
massive growth in AI investment.
It's like the hype cycles of 99in many ways, or maybe more
recently with the wholeblockchain NFT boom.
So, from the perspective ofwhat you folks see in your

(28:41):
proprietary data, what signal doyou look at in the private
market to distinguish afinancially successful
investment or sustainableinvestment in genuine structural
AI innovation from short-termmomentum-driven speculation that
risks creating a financialbubble amongst AI startups?
So, are you looking for abubble?

Jeff Perry (28:57):
So I you know, I don't know that that's like
Carter's role in this lookingfor the bubble.

Yeah.

Jeff Perry (29:02):
Yeah.
I mean, so here's where we feelit.
I don't know that it's likeit's our role to predict the
bubble piece, but like when weknow that there are X new
companies being created everymonth and coming onto the
platform, like that tells yousomething is happening out there
in the market that isgenerating more companies being
created.
And then you see more fundsbeing raised.
So we have, you know, repeatfund admin customers that are

(29:22):
raising new funds.
And the purpose of the raise ofthe new funds is to invest in
AI companies, then that tellsyou from both sides, the the
founder side and the investorside, that there's signal out
there that this pocket is beingcreated.
Whether it's a bubble thatbursts or not is for others to
kind of figure out how thatplays out and like the actual
productivity or you know,success of those companies and

(29:44):
the longevity of it moreimportantly.

That's great.
It's interesting to know.
And I'm sure that your dataanalytics group is just looking
at the macro data over differenttimes.
It must be an interestingstudy.

Jeff Perry (29:53):
So yes, follow Peter Walker.
He's phenomenal.
He's got all the data insightsfor you.

All right, that's awesome.
Well, Jeff now comes.
Fun part, we're gonna play thegame.
This is where you get to have alot of fun with me.
Welcome to the Spark Tank,where entrepreneurial excellence
meets athletic excellence.
And today we're discoveringwhat happens when you combine
hyper-growth revenue leadershipwith hardball heroics.
We're thrilled to have JeffPerry join us at a revenue
powerhouse who scaled Carta from20 million to 450 million

(30:20):
dollars in ARR and knows a thingor two about clutch performance
under pressure.
So, Jeff, you played NCAbaseball at Santa Clara
University from the diamond tothe boardroom.
You've always understood thatgreat teams win championships,
whether that's a World Seriesring or crushing a revenue
target.
So with the World Series nowupon us, we're putting both
sides of your expertise to thetest with a stat or fiction.

Jeff Perry (30:43):
Okay.

Baseball and business records challenge.
We're gonna alternate betweeniconic World Series moments and
jaw-driving private companygrowth stories.
Each question presents aremarkable statistic and
achievement.
Your job is to figure out whomade history, whether it's a
legendary player stepping up inOctober or a visionary founder
building a unicorn.
Let's see if your ability tospot a winner is as sharp on the

(31:06):
baseball field as it is in therevenue trenches.
So you ready, Jeff?

Jeff Perry (31:10):
I'm ready.

All right, this is gonna be fun.
And as I told you before, Ifound this hard.
So it doesn't matter how manyget right, we're gonna have fun
with this.
So round one, World Seriesedition, uh the business
connection.
All right, here's the stat in1919.
This team became the firstfranchise to sell World Series
radio broadcasting rights,pioneering the concept of media
monetization in sports.

(31:31):
What makes it unique?
This deal laid the foundationfor the multi-billion dollar
sports broadcasting industry weknow today, transforming
baseball from gate revenue intoa media empire, a business
tie-in.
Just like early tech companiesfiguring out digital
advertising, this team inventeda revenue stream that didn't
exist before.
All right, which team uhachieved this feat?

(31:53):
Remember, this is 1919.
Okay, A Chicago White Sox, BCincinnati Reds, C, Boston Red
Sox, or D, New York Yankees.

Jeff Perry (32:04):
D, New York Yankees.

Sure about that.

Jeff Perry (32:06):
No, but that's my answer.

You said it with such certainty.

Jeff Perry (32:11):
I didn't know if you I think I might be right, but
we'll see.

All right.
Actually, the answer, and I wassurprised about this.
I would have picked the samething as you.
B Cincinnati Reds.

Jeff Perry (32:19):
Oh, wow.
Interesting.

Yeah, the Cincinnati Reds were pioneers in
sports media monetization,understanding that broadcasting
games could create new revenuestreams beyond ticket sales,
kind of like how modern SaaScompanies discovered recurring
revenue models.
So who knew was the CincinnatiReds, the big red machine of
they won those World Series inthe mid-70s.
I used to root for them becauseI was born in Ohio.

Jeff Perry (32:40):
Yeah, good for them.
It's been a little bit of adrought recently, but yeah.

Back then they were good.

Jeff Perry (32:45):
That's right.
Yeah.
And the red machine for sure.
The big red machine wasexcellent.
Yeah.

Okay, round two.
Private company growth edition.
Here's the stat.
This fintech company reachedone billion dollars in valuation
in just two years fromfounding.
One of the fastest paths tounicorn status in fintech
history.
They achieved this byeliminating traditional banking
infrastructure and building amobile first challenger bank
that resonated with millennials.

(33:10):
Which company achieved thisfeat?
We're gonna give you fourfintech companies.
A affirm, which is buy and I'llpay later.
B Robinhood and Trading.
CHIME, low-fee digital bankingthat just went public recently.
D Coinbase, which was in thecrypto brokerage market.
This is a tough one.
So A, B, C, or so affirm, RobinHood, Chime, or Coinbase.

Jeff Perry (33:30):
Uh Robinhood.

Why do you say Robinhood?

Jeff Perry (33:33):
Because if you mentioned it took on a younger
generation, motivated them to beinvesting, and that's where I
went with the answer.

I would have thought so too, because I
thought, yeah, Robinhoodexploded during that time,
especially in what 2021, 2022.
Actually was Chime.

Jeff Perry (33:49):
Wow.
Okay.

Yeah.
I mean, who knew?
They hit unicorn statusdemonstrating how fintech
startups could leverage mobiletechnology and simplified user
experience to capture marketshare from traditional banks at
unprecedented speed.

Jeff Perry (34:01):
Wow.
Amazing.

I frankly I could have picked any one of these
four.

Jeff Perry (34:03):
Like all very successful stories.

Super fast growth.
So that was a tough one.
Round three, World Seriesedition, the pitcher power play.
You're gonna go back in historyon this.
So the stat, only 15 home runshave been hit by pitchers in
World Series history.
But these two pitchers haveeach hit at two home runs in
World Series play.
So they account for four of the15.

(34:27):
Since pitchers are notoriouslyweak hitters, as you know,
having two World Series homeruns represents an extremely
rare combination of pitchingexcellence and hitting ability.
Here's the business tie-in.
Like a founder who excels atboth product development and
sales.
Imagine that rare dual threatcapability that creates
competitive advantage.
Which pitchers achieved thisfeat?

(34:47):
A Bob Gibson and Dave McNally.
B uh Sandy Colfax and WhiteyFord.
C, Joe Blanton and KurtChilling.
D, uh Babe Ruth and WalterJohnson.

Jeff Perry (34:59):
D.

Yeah, I would think so too.
Freaking Babe Ruth was one ofthe best hitters and pickers
ever, you'd think.

Jeff Perry (35:05):
Yeah.

But it's it's A, Bob Gibson and Dave McNally.

Jeff Perry (35:09):
Oh, really?
Okay.

I can't I couldn't believe it.
I was gonna tell you like,don't say Joe Blanton and Joe
Kurt Chilling.
Those were AL, like KurtChilling was an AL pitcher.

Jeff Perry (35:17):
Well, until he was with the diamondback.
That's true.
That's right.

But I don't think he was much of a hitter.

Jeff Perry (35:21):
Or the Phillies.
Yeah, yeah, you're right.
Actually, no, when he was inthe World Series, he was Red
Sox.
So yeah, that's right.
He really wouldn't have been,he would have been DH4 then.
Yeah.
I like the game.
I'm just not very good at yourgame, Rajiv.

I think the game is great, and I'm sorry you're
not getting, but it is fun, andI'm learning a lot because I
frankly, like you, would havegotten all three wrong.
So Bob Gibson and Dave McNallywere the only pitchers to hit
two World Series home runs each,demonstrating rare versatility.
They were the shoheotani oftheir time.
Like business leaders whomaster both technical execution

(35:51):
and commercial success, thesepitchers proved that elite
performers can excel acrossmultiple domains, a valuable
lesson for today's modern fullstack executive.
All right, here's number fourprivate company growth edition.
And again, this one's reallyhard too.
So they didn't give me anylayups.
Here it goes.
The stat.
This company grew from zero toone billion dollars in ARR in

(36:12):
approximately five years throughpure product-led growth with no
traditional sales team for mostof that period.
They proved that exceptionalproduct design and viral
adoption could replacetraditional enterprise sales
motions.
Which company achieved thisfeat?
And you have four choices.
Zero to a billion AR in fiveyears.

(36:35):
A was it Slack?
B Figma.
C Notion D Canva.
As a hint, I've had BillMesitis on my show, if you know
who he is.

Jeff Perry (36:48):
I don't know Bill.
I'm gonna say B.

B, Figma.
You would think it would beFigma.

Jeff Perry (36:53):
Someone tells me I'm wrong again.
Yeah.

That's what I was trying to idea with that one.
Bill Mesitus was at Slack.

Jeff Perry (36:58):
Oh, okay.

And at DocuSign, I think it was at was he?
No, not DocuSign.
He was at Zendesk.
So yes.
He was a CMO and CRO there atSlack.
And that was one of the bigthings that they did is it was a
pure product left growthstrategy.
I was surprised actually thatthey went from zero to a billion
ARR without a traditional salesteam.
I I don't know how you do it,but you know, if you have an
amazing product, it can happen.

(37:20):
And it proves that viraladoption and exceptional UX or
user experience can driveenterprise sales.
It's the most amazing thing.
Definitely.

Jeff Perry (37:28):
And and drives the network referral effect as well.

I mean, I think that's what you're living in,
right?
It's that's right.
It's that you you guys are socleverly going after like you
know you have the cap tableoffering and it just allows this
network effect that happens.
That's just uh I think it's aflywheel that everybody wants.

Jeff Perry (37:44):
That's right.
That's right.
Yeah.

Somehow Slack did it.
Well, I think the way that youwould think about the way they
did it was because they focusedon productivity.
And it if you're only workingwith one person in the company,
it's not of any value.
And so you give it to two orthree, and you have a free
version.
Before you know it, you have adepartment, before you know it,
you have the whole companyjumping in.

Jeff Perry (38:03):
Yeah, interestingly, when I joined Carta back in
late 2018, as they were thefirst year or so, Slack was our
largest customer.
And there was a point wherethey were headed toward IPO and
wanted to remain on Cartaplatform uh through IPO and
become a public company.
We wisely decided to work withthem.
Henry worked with their execteam to decline the opportunity

(38:24):
to do that, which had to havebeen really difficult for us to
decide to do at that timebecause it would have been such
a headline uh win as takingsomeone from private to public.
The reality is, had weattempted to do that, we likely
would have failed miserably atthat time and created a terrible
experience for them, whichwould have set us back
tremendously.
And so sometimes that like theshiny object right in front of

(38:45):
you, like it's best to say,like, is this the right thing
for us at this size and stagenow?
And so we ended up not, wehelped transition them off of
Carta to another provider to dothe public piece of it.
But we had we we worked withthem for many years.

I gotta say, that is so ballsy.

Jeff Perry (38:59):
Totally.

It must just hit you during that time.
Like, here's a hugeopportunity.
It takes us into a whole newdimension.
We open up that whole market,it's a natural outflow of what
we're already doing.

Jeff Perry (39:08):
Exactly.
Yeah, and there was, you know,they were the the darling of you
know, private to become publicand IPO.
So to have to respectfullydecline and and then sort of
admit where we were at from thepublic offering at that time.
I thought was pretty cool.
But Henry's done some really,you know, amazing things from
that perspective of justunderstanding like what needs to
be done to make the product andthe experience better for
customers, even if it meanssacrificing like revenue or or

(39:31):
different opportunities.
Another example is about a yearbefore I got to Carta, they had
signed so many customers thatthe implementations team had
gotten behind and couldn't keepup with getting the cap tables
implemented.
So he literally paused salesfor, I believe it was about two
months, and said, everysalesperson is now becoming an
implementation person, effectiveimmediately, and helping us get

(39:53):
through the backlog to makesure everyone that we had signed
up had been properlyimplemented.
It did a couple things.
Number one, it cleared thebacklog and got us caught up,
and then we resumed sales, butit also taught all the
salespeople at that timeactually what a company goes
through to get implemented onCarta.
So they were that much betterprepared for the call they were
doing with prospects in thefuture because they knew the

(40:13):
experience that they were gonnago through.

Yeah, I mean, they gain empathy.
It's so powerful.
Totally.

Jeff Perry (40:17):
Yeah, I find it such a remarkable move at that time
when like the pressures offundraising and showing, you
know, rep posting revenuenumbers and saying, like, we're
gonna pause revenue right now tomake sure we get this part of
the business right.
Like, talk about a bold move.
That that definitely was, andthat that was 2017.

Wow.
So, Jeff, if you were the CRO inthat spot, what would you have
said?

Jeff Perry (40:38):
I would have said, Henry, can we maybe go grab a
beer and talk about this?
Because I'm not sure you'regonna change my quota and target
for the team for that timeperiod.
So actually he would haveextremely reasonable and like
always pushes us to always thinkabout doing the right thing.
It's one of the things I I loveabout my experience here is you
know, it's not always about thenumber.

(40:58):
Of course, the number isimportant, but it's about like
he calls it inputs.
Are you doing the right inputsto make the business better?
And that was a perfect exampleof like do the right input to
get the business right.

That's amazing.

Jeff Perry (41:09):
But yeah, we would have had an interesting
conversation for sure.

It would have been it'd be great, what?
You want to do what?

Jeff Perry (41:14):
Yeah.

And and he even talks about it in some of his
conversation betweenmissionaries and mercenaries,
right?
This is where you have toreally go into yourself and say,
why am I here?

Jeff Perry (41:25):
And that's a that's a missionary moment right there,
right?
Like, do you believe in thecause?
Are you behind it?
Help support it, do whatever ittakes to make a great customer
experience, and then we'llfigure out the next thing from
there.

It's a tough test, yeah.
And it's a great one.
So, Jeff, did you always knowyou wanted to work in
technology?
Was there like a specificmoment or project that sparked
your passion?
How'd you discover it?
What got you sparked?

Jeff Perry (41:45):
You know, I as you mentioned, I played baseball at
Santa Clara University and I wasmaybe the kid in the category
of like don't know exactly whatyou want to do after college.
And so I had an opportunity tostart working at Merrill Lynch
through a connection that I had.
And it was entry level to theSeries 7, Series 63, get
license, help do trading.
I got paired up with a seniorbroker on the team at that point

(42:06):
that I learned a ton from.
And that's where I startedworking the cashier window in
the evenings.
And we actually had clientsthat would come deposit cash
checks and stock certificates.
And I vividly remember one ofthem being an eBay stock
certificate that was, you know,ended up being, I did the
calculation worth hundreds ofthousands of dollars that I was
depositing into this client'saccount.
And I remember this vipablemoment of like, do I want to be

(42:27):
the person that's trying to helpreinvest those shares
somewhere?
Or do I want to go to one ofthese tech companies and
actually receive equity likethat individual did?
And so, you know, look, Ilearned a ton in my time, my
short time at Merrill Lynch, andI was I was younger and
impressionable at that time incareer.
But that got me an opportunityto knock on some doors and you
know, had a door opened atOracle.

(42:48):
And that's that's where Istarted kind of in the tech
space.
And I actually did sales, butfor the marketing team, so
exhibits, sponsorships for theopen world conference, which
ended up becoming the DreamForce Conference over time.
The, you know, and so that wasmy first sort of entry into the
tech world.
I saw this massive partnerecosystem around Oracle and
thought, wow, there's all theseother companies out there.

(43:08):
I then got into the productsales team and I did a little
bit of everything from databaseto middleware products.
I moved into the hardwareorganization when we acquired
some microsystems.
I always just kind of said,like, keep the doors open and
I'll raise my hand to help doand contribute wherever I could.
And that always led to whateverthe next opportunity was.
And, you know, here we are, youfast forward all these years

(43:29):
later, and I come to Carta, thecompany that has eliminated the
stock certificate that I waslike chasing, you know, 25 years
earlier.
So amazing story.
Yeah, it's funny how it comesfull circle, but I've been
fortunate to have, you know,great stops along the way, great
mentors and people that liketook a little bit of a leap of
faith and believing in me totake the next opportunity or
next responsibility.
I had that many times over atOracle, had an opportunity, you

(43:51):
know, with Lauren Al Hadiff andhis team at DocuSign to be
there, you know, and help growand scale the SB teams and some
of the verticals, and was therethrough the IPO and then had an
opportunity to say, I want tostart even earlier and smaller
at and Carta found me and Ifound Carta kind of
simultaneously.
And one thing led to another,and we're roughly 20 million in
ARR and you know, healthybusiness.
But it's like, who would havethought it could, you know,

(44:13):
evolve into multiple businessesand multiple products inside of
each business?
And now the 20 million is 500million and beyond, and we're
we're headed to a billion plus.

Did you know that when you first got in?

Jeff Perry (44:23):
I mean, does anyone know?
Like, are you are you hopeful?
I remember like sort of lastmeeting with Henry prior to to
signing was at that Dutch Goosein Menlo Park.
You know, we we had a beer anda burger and talked about like
the potential of the company,and a lot of that has come true,
but I would say it's come truedifferently than like we would
have thought in that booth atthat time having that burger.
It just, you know, it wouldhave been like the cap table

(44:45):
business and how that continuesto expand and grow and what that
leads to.
It wasn't as much about, youknow, the vent the fund admin
business and private equity andLPs and all these things that
seven years later we're now,we're now doing.

I don't think any of us would have anticipated,
even those who are into tech,that private equity or companies
staying private longer would beuh such a big trend.
How many, you know, trillionsof dollars are now in private
markets, not in public markets.
We wouldn't have forecast that.
I mean, Dodd Frank, that wasprobably one of the contributing
reasons, but it's also thatit's easier to get done or stay
private when there's pools ofcapital there for you.

(45:19):
So yeah.

Jeff Perry (45:19):
So, you know, when I back in those days when I was
meeting with Henry and Charlie,and you know, it felt like Cardo
was onto something.
This could be, you know, agreat opportunity.
As it turned out, it evolvedover time.
And you're right, like the thelandscape is totally different
now.
I mean, back then companieswere on a chase to get to a
hundred million ARR, and thatmeant if you do that, you can
IPO.
And now we're in a totallydifferent world now.

(45:39):
And so, like, what is an IPOready company?
And then more importantly, whatis a IPO ready and can be
successful beyond that is themore important thread to pull
there too.
Which is one of the things, youknow, most proud about is what
we built here is being likethoughtful and methodical in how
we do it and being at a growthtrajectory that you know we we
aspire to be, and also you know,at a level of profitability

(46:01):
too, so that we've hit both endsof the metrics.

That's awesome.
So we always ask our guests toname a historical event or
person or movement that inspiresyou.
And you answered, quote, peoplethat perform under pressure,
like Tom Brady.
I think go to high school withthem, and people who are
motivated by fear or failure,like Larry Ellison.
You didn't go to high schoolwith him.
What in particular about themlights you up?

Jeff Perry (46:24):
Well, thank you.
Yeah.
So yeah, I did go to highschool with Tom Tommy back in
the day.
That's many years ago now.
And so it's actually been funto follow someone that you you
feel like you kind of knew as ayounger kid and watch progress,
and then all of a sudden,life-changing experience, and
then you know, uh, you know, thethe folks that you know we knew
him growing up and you knew hewas uh, you know, a great
athlete and all these things,but then to watch it happen on

(46:44):
that stage and how he handled itis like all of us have taken
some pride in as well.
And you you just be you can'thelp but become a fan of sort of
the pressure and the microscopethat you're under on that
stage, and then the ability tolike not just do it once, but
like multiple times repeatedlydemonstrate that consistency in
performance.
And you know, I've watchedenough and I've seen enough on

(47:05):
it.
Like sometimes he's got to bethe guy that had to be probably
tougher on teammates and be theguy that's motivating and
driving.
Sometimes he's the raw-rah guy.
And so, sort of knowing yourplace in this, and I feel like
you try to take a lot of thatinto what we do as sales leaders
too, is like you know, you ridekind of the highs and lows, but
you also keep this sort oftemperament of like you've been
there before, you know whatsuccess looks like.
You know that it's not alwayseasy to be successful, and

(47:27):
sometimes you're gonna have somefailures, and so you learn from
that and you pick up the piecesand you move on.
So I think there's a lot I'vetaken from just watching Tom uh
over the years, and obviouslyit's just fun to root for
someone that you you you kind ofknew when you were younger.

It's incredible.
Yeah, I yeah, I grew up in NewEngland, so I'm a Pats fan, and
so I studied yeah everything Tomand Billy Belly Jack have done.
So it's amazing.
But then you mentioned fear offailure, like Larry Ellison.

Jeff Perry (47:50):
So you know, I actually feel like fear of
failure.
I've always operated that way.
Like I've, you know, I went toSanta Clara University, pitched
there.
I had a fear of failing becauseI would let my team down.
And if I let my team down, Iprobably at some point would
like lose my role in and and myopportunity for playing time or
or time to contribute.
And so I always wore thislittle chip on the shoulder of

(48:12):
fear of failure.
I actually think that was ataboo statement.
There was a time where it'slike, if you say that, that's a
weakness and like you shouldn'tsay that.
I have since heard more people.
I recently read something aboutLarry Ellison operating that
way too.
And having worked at Oracle,that resonated with me.
So I've always like tried tojust embrace it versus like hide
that like I I've operated thatway and just say, like, yeah,

(48:33):
like I don't want to fail.
I don't want Carter to fail.
I like I want to be successfulboth personally and I want my
teams and my people under me tobe successful.
So operating with a little bitof that fear of failure, I think
keeps you sharp, it keeps youmotivated, it keeps some edge to
you.
For me, it keeps me likeenergized and excited about what
we do and who we do it with.
So I'm not letting go of thefear of failure.
I'll always operate that way.

(48:54):
Yeah.

I think that's a great way of putting it.
I it's unique and interesting.
And you know, we all wake up asentrepreneurs or business
leaders.
You know, we have impostersyndrome, right?
We wonder, can we keep thisgoing?
And what keeps us going?
And I promise this, can Ideliver it?
Right.
And every day you have to wakeyourself up and say, I can do
it.
But that fear of failure is oneof the motivators.

Jeff Perry (49:13):
Totally.
And one of the things I lovemost about sales leadership is
to me, is very much likepitching in baseball.
Like there's such an individualcomponent to being the pitcher
of the team, yet you're stillpart of this incredible team
sport, and it takes everyonelike pulling their own, you
know, part of the weight to besuccessful.
But a lot of the onus is on thepitcher to perform and the
pressure is on because that theycan have a significant outcome,

(49:35):
both positive or negative, orinfluence of the outcome to that
positively or negatively.
So I've kind of thrived in thepressure of that, which I feel
like has translated really wellto the business side.
But it also I I love the teamthat I work with and the team
that I'm surrounded with.
And we celebrate the successestogether and you know, we work
through the challenges togethertoo.
And that's the beauty of theteam sport aspect.

So, Jeff, if you could magically make one daily
task take zero time, what wouldyou choose?
And what would you do withthose extra minutes?

Jeff Perry (50:03):
I would say it's probably some of just the like
the operational roadblocks thatcome up.
It's not like one specificthing, but like I'll start my
day and I'll get some slacksfrom someone that, like, hey, we
have this issue with, you know,someone's comp was not correct,
or an offer letter didn't gooutright, or the levels the same
between this business unit andthat business unit for a level

(50:24):
four AE.
And it's like some of thatstuff, it just like it, it's
roadblocks, it's it's timesucks.
It doesn't just, you know, takemy time.
I then have to go triage and itloops everyone else in.
Also, like we just spent like20 business hours on this
ridiculous thing that franklyshould have just been solved
really quickly or should havenever been an issue.
So if I could eliminate some ofthose things, which I don't

(50:45):
really know how to do, they'realways going to come up.
I think that's a sign of likegrowing, evolving business.
But with that, I would takethat and do, I'd like to do two
things.
I'd split that time.
As you get bigger, it getsharder and harder to stay super
connected with folks that aremaybe a couple levels below.
I feel like I used to bereally, really good at that.
And then as things evolve, itjust gets harder.

(51:05):
So I'd spend some time there.
And then, you know, what we'vereally learned over the last
couple of years is the more timeI and the rest of the exec team
can be in front of customers, Iwould use the time that way
instead.
Yeah, it's cool.
It's how you create greatexperiences, it's how you create
raving fans that tell the nextprospect that they should work
with us.
So I would use the time thatway.

All right, that's a great answer.
If you could swap lives withsomeone for just one week to see
what it's really like, whowould you choose?

Jeff Perry (51:31):
Maybe the president.
That'd be an interesting seat.
I don't think it's you knowsomething you'd want like full
time, but a window into thatworld would be really
interesting.

That would be interesting.
I think there's something like30 plus people that arrange
president's calendar.
Really highly scriptedsituation where the situation is
scripted yet extremely dynamic.

Jeff Perry (51:50):
Definitely.

From subject to subject.
So it's it's a it'd be veryinteresting to sit through that.

Jeff Perry (51:54):
I recently went to the Ryder Cup and I thought it
would be fun to like switchspots with a golfer.
Then you realize like theamount of eyeballs on you just
hitting that one shot would bepretty nerve-wracking.
So that could be interestingtoo.

That is that is very interesting, kind of like a
picture, right?

Jeff Perry (52:12):
Definitely very much like that.
Yeah.

Okay.
What's a social situation thatyou used to dread, but now you
actually enjoy?
And what changed?

Jeff Perry (52:19):
I I would say it's probably public speaking.
I think, you know, most peoplekind of dread that, I think.
And for me, I now like I reallyenjoy it.
Like I one of my favorite daysof the year, a couple days, is
our sales kickoff.
And I, you know, I look back atmy early days, you know, I
shared Merrill Lynch and eventhe early Oracle days where I
just hadn't had opportunities todo that.
And I would have thought ofmyself as less confident or the

(52:41):
ability to like stand in frontof an audience of 500 people and
you know, do sort of MC and runof show and do you know, state
of state of the businesses andall those things, like that
would have been high pressurefor me.
And now I feel like that's mymoment.
I love it.
It's my chance to like connectwith our team and our people and
share what we've done andcelebrate the successes, and
then sort of put a bow on thatand talk about like the next

(53:02):
year and the targets that we'regoing after and how we're gonna
do it and the resources we havebehind it, like kind of thrive
in that stuff now.
Yeah, if you asked me that 20years ago, I'd be like, there's
no way I would do that, youknow?
And now I love it.
It's one of the things I reallyenjoy about the job.

That is amazing.
I think it's that thing whenyou walk in, you might be really
nervous about it because you'relike, Did I miss something?
Or something some magical thingI need to say.
And then the minute you start,you start to connect with people
and you start to look in theireyes and you feel that
connection with them.
That's when things change.

Jeff Perry (53:32):
So to me, I'm so glad you said that.
It's very much to me like whenI was in the bullpen warming up
to start a game, the 15, 20minutes before is very much like
when you're before you're goingout on stage to to kick off an
event like that.
And you have a little bit oflike the rehearsal going on in
your head and thinking about thethings you want to, the message

(53:52):
you want to, you know,communicate.
There's a little bit of likeanxious energy.
There's a little bit of likebutterflies, there's a little
bit of like keep the chip onyour shoulder we talked about.
And then all of a sudden, likegame starts and you throw the
first pitch and you go, orlights go on on the stage and
like you take over themicrophone and like you start
your messaging, and then youhave that connection of like
channel focus.
Like it's you know, when I waspitching, it was like laser

(54:14):
focus on the catcher and gettingthat hitter out.
And like you get on stage andit's like, okay, I don't even
need the slides.
I know my message, I know whatI'm talking about, and like
you're just because you'reprepared and all the practice
you put in to make it feel likeit's natural in what you do.
And so there's a there's somany similarities to to all
these things that that cometogether.

It is amazing.
Jeff, how about this one?
What's something you'reembarrassingly competitive about
that doesn't matter at all?

Jeff Perry (54:37):
I don't know.
I I I'm pretty competitive.
I think about everything.
Like I'm playing golf uh thisweekend with about 30 dads from
my kids' schools that we've beenfriends with for you know
better part of 15, 20 years, andthere's two teams set up, and
it's like I'm my team, I want myteam to win, you know.
And does it really matter?
No, because we're all gonna gohave a great time and it's gonna
be like, how's this kid doing?

(54:58):
Tell me about you know, whereuh how many of them have started
college now, so does it matter?
No, but it's like later thatnight when we're at the dinner
together, we want to be on thewinning team, you know.

Again, give the other guy a lot of crap for of
course, yeah, exactly.

Jeff Perry (55:11):
Yeah.
So I think you know, it's it'sthose type of things you learn
along the way.
Some of us are just wired thatway.
Like, and you know, I actuallythink a lot of people that have
maybe met me, they didn't know alot about me.
I think a lot of people likeIcarta early on thought I was a
bit more quiet, maybe a littlebit less like competitive.
But then once they got to knowme, they realized like you don't
always have to be the loudest,most outgoing competitive

(55:31):
person.
You can have like the innerfire, the chip on the shoulders,
say like, I'm gonna fight likehell to win every single
interaction that we have.
And some people are just madethat way and others are not.

Yeah, I think you totally nailed it.
It's not the one that'snecessarily so outwardly
boisterous or so outwardlycompetitive.
There are folks that are quietthat are just ridiculously
intense.
It's not until you get intobusiness for a while.
I think even in sales, there'sthat mental thinking that a
salesperson needs to be acertain way.

(56:02):
And I find that's just not thecase.

Jeff Perry (56:05):
And I, you know, the thing I think I've learned
along the way too is like thethe best of the sales leaders, I
think, are the ones that like,or just people leaders, are the
ones that can find the balancein that, right?
Like you have the competitive,whether it's louder or it's the
more internal one.
But then, like, how do youbalance that with being like
genuine and compassionate anddriving and having to give the

(56:26):
difficult feedback or giving therah-rah feedback?
And how do you balance thatwith all the individuals that
you work with or even your peersand counterparts and business
counterparts that you work with?

Yeah, you you see this in coaching of any sport,
right?
You see it right in front ofyou.
Some people are just out thereand they win, and some people
are super quiet and they win,and and vice versa.
So it's really interesting.
So, do you have a favorite lifemotto that you come back to and
share with friends, work, orlife?

Jeff Perry (56:53):
So I grew up in you know private Catholic grammar
schools and high school, that'show you know with with Tom.
I've always just tried tooperate by like the golden rule,
like do unto others as thouwould like to have done to you.
And I feel like that's how I'vetried to live and operate.
And it also like resonates, Ithink, very well in the business
world.
Like, doesn't mean like youhave to always agree with
everyone, doesn't mean likeyou're you're always in friction

(57:15):
with everyone, but you do treatpeople like respectfully.
You give people an opportunityto share their perspective and
and their minds.
And if you treat people fairlyand respectfully, I think you
gain the respect from them alongthe way that earns you the
right to like ask them to go theextra mile for you as well.
And so to me, it's like, yeah,we're selling software and some
services here, but like I'm inthe people business now, like

(57:38):
and have been for decades now.
And it's like, how do you workwith people, whether they're
customers or prospects or yourinternal team?

You have investors, you have board
members, all of it, yeah.

Jeff Perry (57:47):
And so it's like, how do you communicate with
people?
How do you treat people so thatthey want to be part of what
you're doing and building andand they feel like you know, I I
the other motto I use is like,does everyone have an oar on the
boat?
And is everyone paddling theiroar?
Not just paddling it, like, butpaddling in sequence together.
So we're we're you knowsteadying the boat in the same
direction.

It's all about alignment, yeah.
What's your personal moonshot?

Jeff Perry (58:09):
Well, uh right now it's Carta.
You know, I've never thoughtabout it that way.
I really haven't.
Maybe I should, uh, but I justthink about it as someone that
kind of grew up in a modestworld and I was fortunate to
have a great family around meand sort of had the things that
I needed and the support that Ineeded.
I try and like pay that back asbest I possibly can.
And, you know, my hope is thatlike good things happen to good

(58:30):
people.
And so I've tried to do rightby people in my other stops
along my career and hopefullymade a bigger impact in doing
that at Carta.
And hopefully Carta becomes areally big thing.
And then that provides someopportunities to figure out what
the next thing is to do to makean even bigger impact.
And whether that's in like asimilar role or a different type
of role, but what we can do tolike continue to give back and

(58:51):
help.
Like I'm wired that way.
Like, I'll spare you the names,but I can give you the names of
people along each of the stopsof the way that gave me an
opportunity to do things that Iprobably didn't deserve at the
time or had an opportunity toopen a door here or there.
In a lot of ways, the things Iget to do now and will get to do
a lot more of in the future isto pay that back by creating

(59:12):
opportunities for for otherpeople as well.

I think that's one of the most amazing parts about
hitting a certain level ofseniority in your role is that
you're actually paid to giveback.
You're actually paid to coachpeople to lift them up, help
them be successful.
It's a it's a wonderful system.

Jeff Perry (59:26):
Yeah, like one of the most satisfying things I
have now is just seeing people,you know, people that I started
at Carta with that were inentry-level roles at the time
and now are like leading largeorganizations and have a major,
major impact on the current andfuture of the company.
How rewarding is that to watchthe progression that happens.
And then that's the businessside.
You also get to see thesepeople get married, have kids,

(59:47):
like have other adversity inlife, and you deal with all
those things together.
And so, for the amount of timeand effort that we we give to
the workplace and what we dotogether, you also can't help
but like become connected topeople and understand that like
there's more.
To all of it than just like thework aspect to it.

Rajiv Parikh (01:00:02):
Well, Jeff, that's an amazing perspective.
Thank you so much for spendingyour time with me today and
sharing with our listeners uhyour experience and what what
you guys have accomplished atCarta and many stops along the
way.
It was so much fun to learnabout you and your life and
really what makes what buildsgreat success and what builds
great growth.
There's always challenges, butthere's that way of getting
through it.
And I appreciate your timetoday for that.

Jeff Perry (01:00:24):
Vajdeev, thank you so much for having me.
I had a great time with you aswell.
Really enjoyed it andappreciate you uh having me on
the show.

Rajiv Parikh (01:00:35):
That was a really great episode.
You have a proven winner likeJeff, who was walking through
this really amazing backgroundwhere life came full circle to
him from delivering stockcertificates to delivering
options electronically andeverything in between.
I think what Jeff has smartlydone in his life is focus on

(01:00:56):
network-oriented businesses andput himself out there in tough
situations, but he's alsopatient in how he gets to where
he is.
A lot of what he does comes outof his experience playing
sports and being a pitcher,being on the mound, having
everyone watching you,delivering in key moments, but
also knowing that once that ballleaves his hand, that's when

(01:01:18):
anything can happen.
And it is really about the teamand it's about the next pitch,
and it's about how you adjust.
And you can sense that.
He's in a company with manydifferent business lines, but
coming from a core capabilitythat now keeps expanding.
And I appreciate his insightabout his CEO and what
situations work, his drive aboutwhat got him into technology
and what he thinks about when itcomes to leadership.

(01:01:39):
And you can sense thathumility, that sense of purpose,
that drive, and that care forthe people on his team, his
peers, as well as all the peoplearound him.
So it was a really amazingepisode, at least for me.
I learned a lot.
So I hope you did as well.
So thanks for listening.
If you enjoyed this pod, pleasetake a moment to rate it and
comment.
You can find us on Apple,Spotify, and YouTube, and

(01:02:01):
everywhere podcasts can befound.
This show is produced by AnandShah and edited by Laura Balant.
They do a fantastic job atthis.
I'm your host, Rajiv Parit fromPosition Squared.
We're a leading growthmarketing company based in
Silicon Valley.
Come visit us at position2.com.
This has been an F Funnyproduction, and we'll catch you
next time.
And remember, folks, be evercurious.

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Revenue Culture That Survives the Boom/Jeff Perry - Carta, Cap Tables, Private Capital ~ Spark of Ages Ep 49

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.css-14f5ked{margin:0;word-break:break-word;display:-webkit-box;-webkit-box-orient:vertical;box-orient:vertical;-webkit-line-clamp:2;overflow:hidden;}Revenue Culture That Survives the Boom/Jeff Perry - Carta, Cap Tables, Private Capital ~ Spark of Ages Ep 49