November 25, 2025 • 23 mins
This bonus episode dives into how Cristina Cordova (Stripe’s 20th hire, early leader at Notion, now COO at Linear) spots exceptional talent early, and how she pressure-tests whether a team and product are truly worth betting on. It’s a crisp, tactical look at evaluating “spikiness,” finding beloved products (even with limited data), and building GTM the right way from day one.
Cristina Cordova is a seasoned operator who has scaled some of the most iconic companies in tech. At Stripe, she built and led partnerships that became a foundational revenue engine, including the pivotal deal with Shopify. At Notion, she helped turn viral adoption into a durable distribution strategy powered by community. Today, Cristina is the Chief Operating Officer at Linear, where she’s applying her experience building high-velocity GTM engines to the next generation of developer-first tools.
This is a clip from the full episode with Cristina (an inside look at the judgment frameworks behind Stripe, Notion, and now Linear) and the practical filters every GTM leader can use to pick winners early.
Discussed in This Clip
- How to recognize “exceptional” even outside your own domain
- Finding early proof a product is truly beloved (signals > vanity metrics)
- Starting with a sharp market wedge, then earning the right to expand
- Why founders who excel at something—anything—tend to excel at company-building
- What to expect from early operators: founder mode and bias to execute
- Sales hiring for technical buyers (and why quotas can help earlier than you think)
- Aligning tightly with founders as an exec: relationships drive outcomes
- How to assess GTM on day one: ride-alongs, raw customer feedback, ground truth
Highlights
00:00 — The difference between good and great—and how to spot it across functions
00:12 — Why this clip hit: Cristina’s framework for identifying exceptional people early
01:17 — Looking for skills you don’t have—and recognizing greatness outside your lane
03:38 — Evidence a product is beloved (Stripe on Hacker News, Notion on Twitter)
04:49 — Start with a wedge; win big later (why early enterprise skeptics don’t matter)
07:54 — “Spikiness” and unconventional signals of excellence (Minecraft servers to sales)
12:52 — What great early leaders do: see problems, create strategy, then execute
16:45 — Sales at product-led companies: hire technical sellers, set quotas sooner
21:31 — How Cristina assesses GTM on day one: ride-alongs, direct customer observation
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Transcript
Episode Transcript
Available transcripts are automatically generated. Complete accuracy is not guaranteed.
Cristina Cordova (00:00):
You can tell the difference between someone
who's good and someone who'sgreat if you are exceptional at
something yourself.
You are better at kind oftrying to spot that
exceptionalism in other people.
Sophie Buonassisi (00:12):
You've scaled from less than 40 people
to thousands of people inorganizations.
And you've seen billion dollarsgo to market and you've seen it
built from scratch.
Listeners replayed what camenext more than any other moment
in the full episode withChristina Cordova, Strike's 20th
employee early leader atNotion, and now the COO of
Linear.
What you're about to listen tois that segment.
(00:33):
She outlines her framework ofstrategies for identifying
exceptional people early andevaluating the team's worth
betting on.
Hope you enjoy it.
And if you do, could you do mea favor and subscribe if you're
not already?
Thank you.
Appreciate you.
It helps us continue to bringon the guests and cover the
content that you're most excitedto hear about.
All right, let's get into it.
Other things that you look for,other than being whisked away
(01:06):
in a plane up top and anairline, but overall
curiosities, it sounds likeinvesting in long-term durabil
solutions.
Are there other things you lookfor?
Cristina Cordova (01:17):
Um so I would just say like talented in in
lots of ways that I am not.
It's part of it.
Yeah, exactly.
It's like I want a foundingteam to have a lot of skills
that they can bring to thetable, but skills that I can
(01:37):
observe are not my skills, but Ican still understand that it's
exceptional.
There are people that you canobserve and you're just like, oh
yeah, that's an engineer.
And and and and then whenyou've been working in this
industry long enough, you cantell the difference, even if
you're not an engineer betweensomeone who's good and someone
who's great.
And sometimes that might be indomains that are outside of what
(01:59):
you would think, like anengineer interacting with a
customer and try trying tounderstand their technical
feedback and how to fix it.
Sophie Buonassisi (02:06):
Yeah.
Cristina Cordova (02:07):
Um that's an interaction that you can observe
as someone who's notnecessarily technical to
understand if they're trulygreat at what they do.
So there's a lot that I thinkabout when I think about
founders, where it's okay, ifyou're a designer, I want you to
be one of the best designers inthe world.
If you're an engineer, I wantyou to be one of the best
(02:29):
engineers in the world.
And I think it's important thatas founders, you are bringing
the best of the best to thetable because it also helps you
recruit so many other reallyfantastic people too, because
you know what to look for assomeone who's great in whatever
domain that might be.
And then at the same time, Ithink in a lot of ways, you are
(02:52):
looking for exceptional peopleeven in other domains that you
are not familiar with.
So, you know, as an early stagecompany, you do a lot of first
of hiring.
You're hiring your first peopleops person and your first
recruiter and your firstsalesperson.
And as a technical founder, youmay not know a lot about those
domains or understand what's thedifference between good and
(03:14):
great.
But I tend to find that if youare exceptional at something
yourself, you are better at kindof trying to spot that
exceptionalism in other people.
So that's definitely a keycomponent of it.
And then I would say from abusiness standpoint as a whole,
I've generally joined companiesthat are post-having some kind
(03:36):
of product in the market.
Sophie Buonassisi (03:38):
Yeah.
Cristina Cordova (03:38):
So I try to look for a lot of signs that
that product is doing well inthe market.
It doesn't have to be doingamazingly well, right?
And also your interpretation ofthat on the outside is limited
given the data that you have.
But I love products that peoplelove so much that they want to
talk about them somewhere on theinternet, right?
(04:00):
So with Stripe, it was likepeople talking about Stripe on
Hacker News, and I would searchfor people posting about it and
what are people saying, right?
Because I'm also, I was not acustomer of Stripe.
I don't know, is this really agreat product, right?
So I would go talk to peoplethat I knew who were early stage
startup people, and I wouldsay, What are you using for
(04:22):
payments?
Oh, you're using Stripe.
Why did you choose that?
Do you like it?
You know, like those kinds ofthings to try and understand why
they made certain decisions.
Sophie Buonassisi (04:31):
Yeah.
Cristina Cordova (04:32):
And then for Notion, a lot of my perspective
was on Twitter, like, what arepeople saying about this
product, right?
Do they like it?
Do they love it?
Is it controversial?
You know, why?
Linear was very similar.
Like, where can I find thisproduct's audience?
And then what is the audiencesaying about the product?
Sophie Buonassisi (04:49):
Yeah.
Cristina Cordova (04:49):
Um, and I think that can be very helpful
to understand is this a belovedproduct?
Even if the audience is small,right?
And that matters a lot to mebecause, you know, for the most
part, you know, I've I've I'vemanaged literally every type of
function engineering, productmanagement, business, revenue,
all these things, but generallyI am not hands-on building the
(05:13):
product.
And so I would love to see thatthere's evidence that the
people who are hands-on buildingthe product are listening to
customers, know what customerswant, and that whatever they
have built so far is resonatingwith those customers.
And then I think what you tendto see is that people who are
maybe detractors or don'tbelieve in the brand might just
be bigger companies, right?
(05:34):
That are, oh yeah, like Stripe,that's for startups.
You know, that's what peoplewould say in the early days when
they were like, yeah, that'sprobably not going anywhere.
And then you realize that likeevery company starts out with
some kind of wedge in the marketthat they're focused on.
And then eventually over time,if they're successful, they're
(05:56):
able to kind of grow that wedgeand own a bigger share of the
pie.
Um, and for every company I'vebeen part of that's done B2B,
it's been starting with startupsin early stage companies and
then going to gross stagecompanies in mid-market and then
going to enterprise.
Right.
So, yes, the enterprisecompanies really early on are
gonna be like, oh, you're you'resmall, no one's gonna use you,
(06:20):
like that kind of thing.
And then you you're just gonnachange that company's mind.
And it might take you a decade,but you can do it, right?
Yeah.
But you should be resonatingreally well within that wedge
that you have defined is workingreally well.
So those are the things I tryto like suss out.
It's really people and like, isthe product resonating in the
(06:41):
market that you are reallyfocused on at this particular
moment in time?
But sometimes obviously whenyou're looking at a pre-product
company, it's really just theteam.
Yeah.
And that's all you've got,right?
And so figuring out what arethe data points that you do have
and do you find that thecompany is exceptional in one of
team market product areas.
(07:03):
Um and ideally it's all threeand you have a transformational
business in front of you.
Sophie Buonassisi (07:10):
So super cool.
It's really interesting to hearyou actually articulate that
because it mirrors exactly howwe evaluate startups too and
founders.
It really is, you know, two ofthe core areas I heard you stay
was around the person.
We think about that asspikiness.
Yeah.
You know, one of the founderswe invested in was the largest
creator of a Minecraft server.
Super niche and random.
(07:31):
But he was so passionate aboutthis idea that he pursued it.
Same kind of thing of you know,what are people excellent at
and what are they pursuing?
And then similarly with thebeloved customers and just
people being being huge ravingfans of a product.
We look for, you know, peoplethat would essentially be so
unhappy if the product was takenaway from them.
(07:52):
We'd look at that over revenueany day.
Cristina Cordova (07:54):
Yeah.
Sophie Buonassisi (07:54):
Or most days, I shouldn't say any day.
But most days, you know, we'drather have 10 happy design
partners that are paying a tiny,tiny fraction over, you know,
$500,000 in revenue if they'remore disparate logos sometimes.
Yeah.
That's kind of the sameprinciples I heard you say.
Cristina Cordova (08:08):
Yeah, I like what you mentioned around the
Minecraft thing.
It's like, to me, it's like I Iwant to see someone who's
exceptional at something becausethen I know that like when they
make this transition to being afounder, they're gonna want to
be exceptional at that too.
Right.
So whether it's craft or Idon't know, taekwondo, or your
IMO gold, or but those are themore classic, closer to
(08:31):
engineering type things.
Sophie Buonassisi (08:32):
But I didn't know Taekwondo was so
engineering.
Cristina Cordova (08:37):
So that more the IMO gold folks, but or those
people who do like, what is it,like quiz bull or things like
that, right?
Um these like competition mathystyle things, probably closer
to engineering and then maybegood founder, like you know,
you'll see.
But you want people to be goodat something.
That's what we're trying to do.
We're we're trying to buildsomething exceptional.
(08:57):
So having someone who's beenexceptional at something,
whatever it might be, is also areally good sign.
Like you see this even aboutsales leaders.
So many of them are athletes atcollege-level athletes go going
straight into sales.
And it's like, well, yeah, ifyou are someone who's who has
experience trying to get out andlike college athletics, you're
(09:19):
probably gonna be able to pickup the phone, make a lot of
phone calls, yeah, be relativelypersonable, and close some
deals, right?
Uh projection.
Right, exactly.
So things that where you'rejust kind of like, what's the
corollary for what this personhas done historically?
And does that translate to thisnew field?
Whether it's being a founder orbeing an operational leader or
(09:40):
what have you, you know, I thinkthe the interesting thing about
startups is that we're alldoing things that we have no
business doing.
I've never been a COO untilnow.
So, you know, you could arguewhat business do I have doing
this job, right?
I I had never worked at astartup, you know, until I had.
Yeah.
So we're all doing thesethings, I think, for the first
time.
And anyone who's building acompany is building a company in
(10:03):
that specific market for thespecific customer, you know, for
the very first time.
So we're all doing somethingthat we don't necessarily have
experience in.
And it's important to thinkabout A, what are the things
that I do bring to the tablethat are gonna help me adjust to
this problem and and how tosolve it?
And then are there examplesthat exist elsewhere that I can
(10:27):
learn from?
Um, I think the StripeFounders, one of the things
they're really great at, is justbringing in this growth mindset
to everything that they'redoing.
There were times when we weredoing company planning early on,
and they were like, Christina,could you maybe go off and have
some conversations with someother people at bigger companies
(10:47):
about how they do planning andthen bring those learnings back
to us.
Yeah.
Um, and so I went and I didthat and I talked to execs at
Amazon, at Meta, at Google,several places, and tried to
understand how they did planningand then what, if anything,
could translate to Stripe of 500people, I think at the time.
Right.
And at the same time realizingthat Stripe was a very first
(11:09):
principles-oriented company thatwasn't just gonna say, Oh,
well, Google plans this way, sowe should plan this way too.
Because, you know, is that whatmakes Google a great business,
how they do operationalplanning?
I I don't know, but it may notbe, right?
Right.
Or it could be unique to themin a certain way.
Right, yeah.
And so, like, is is the fitthere for your business, like
(11:32):
from this advice that you'regetting, and trying to
understand if it really appliesto you, and then understanding
is what makes this businessgreat, like this particular
thing, or actually, is it theseother things that they're really
good at?
And the operational planningcould be terrible, and it
wouldn't really matter.
Right.
Sophie Buonassisi (11:49):
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(12:32):
Very cool.
And what about the operatorside?
Because you yourself, you'vebeen, I mean, one of the first
business hires for companiesmultiple times.
You assess founders in acertain framework, like we
talked about.
Does the same framework applyto operators when you hire?
Because I've heard you say bethe person that builds without
being asked to.
Cristina Cordova (12:52):
Yeah.
I mean, I think it depends,like if you're if you're talking
about like leadershipspecifically, so some kind of
like operational leader within acompany.
I definitely think I've alwaysappreciated people who have a
more like entrepreneurialmindset.
So founder mode obviously beinga thing, but I I don't think
that solely applies to founders.
(13:14):
I definitely think it appliesto people who are leading in
companies.
And I think that's because themode that it requires of you at
a certain stage in size, whichis a like I have never joined a
company outside of my first jobat straight out of college with
more than 40 people, right?
So I've I've always been veryattracted to companies of a
(13:36):
certain style size and growingwith them over time.
Stripe was 3,000 people when Ileft.
But I think in a lot of ways,starting with companies that are
really small, you're lookingfor people who can see problems
and want to fix them, or see anopportunity and want to go out
and get it.
And I think for a lot ofpeople, maybe in more
(13:57):
traditional environments, arewaiting to be told what to do
and are waiting to be like, oh,what strategy is like, you know,
Christina gonna give me thattells me what I should do this
month.
And it's like, no, no, no, no,I'm hiring you because I think
you can come up with a strategy,right?
Um and you know, the differencebetween a really great
(14:18):
leadership hire and a not sogreat leadership hire is someone
who's coming to you and saying,Hey, you know, Christina, I
think we should change pricingat linear, right?
Or I think we should build outour AMIA team, or I think we
should do this.
And I'm like, this is a greatidea.
Let's have a conversation aboutit, right?
Yeah.
Versus me having to go to themand and necessarily say all of
(14:41):
those things.
Of course, there are going tobe things that I have ideas
about, and that's why I washired, right?
And and bring that to thetable.
But I but I do think I expectthat leaders that I hire are
going to not just think aboutwhat are the things that sh we
should be doing at certainstages or size of business.
Because there are there arethings that are pretty normal.
(15:03):
Like, okay, at this stage weshould start having audited
financials and we should get afinance person and we should,
you know, uh that's veryclassic.
Not necessarily like innovativeor going to transform the
business, though, right?
Yeah.
So if you're gonna spend time,you know, coming up with ideas,
I'd rather it be on the ladderrather than like on the stuff
that yes, we're gonna have to dothat at some point, and
(15:24):
reasonable, like, yes, we can dothat now.
Yeah.
But coming and saying, what arethe things that we're going to
do that can markedly change, youknow, the trajectory of what
we're doing, I think is reallyimportant.
And hiring people that youthink can do that.
But that's not true of allfunctions.
Some functions, like the job isto keep the lights on and keep
things moving and trains runningon time and things like that,
(15:45):
right?
True.
But I would say that for a lotof roles where you can make a
transformative impact for thebusiness, the job of leadership
is to really think through howthat business can transform and
then have the power to go andexecute against it.
Because ideas are great.
We all have lots of ideas, butif you can't execute and get it
(16:08):
done, the ideas don't goanywhere.
And so for me, I've always beena much more execution-oriented
person.
I really like doing things, Ilike getting things done, I like
making progress, but that can'tcome at the cost of thinking
strategically and trying to donew things and being innovative.
Sophie Buonassisi (16:27):
Yeah.
That makes sense.
And I mean, you mentionedyou've scaled from less than 40
people to thousands of peopleand organizations, and you've
seen billion dollar go to marketand you've seen it built from
scratch.
What are you doing now atLanier that you're restarting
that build process?
Cristina Cordova (16:45):
I think there are definitely lessons I've
learned.
Like in at Stripe at the earlydays, I think there was a lot of
fear of salespeople.
Like, as if the salespersonthat we would hire would be the
person who's trying to sell yousomething that you don't need
and all those kinds of things.
And it was like you can findsalespeople who who know sales
(17:07):
and can do it well withoutcoming across in this particular
way.
For sure.
And and so realizing that atearly stage companies the vibes
are important.
And if the founders suss outthat we're hiring salespeople
with the wrong vibes, it's notgoing to work.
Um, but knowing that I'd rathersave us a lot of time.
And instead of hiring peoplewho don't necessarily have sales
(17:27):
experience, hire people who areexperienced in sales, but have
done a lot of technical selling.
So selling to a buyer who is inengineering, product, and
design.
And we almost exclusively hiresalespeople with those
backgrounds, specificallybecause I I know that they have
to come across in a certain wayto not be salesy traditionally.
(17:52):
And that has saved us a lot oftime that I think was wasted,
you know, at at Stripe to kindof figure out, you know, how do
we sell?
What is the strategy here?
What is the approach?
And cut through some of thatinitial work and get straight to
what is the value that we'reproviding and how do we talk
(18:15):
about it, and what is the salesnarrative.
And then finding a team thatunderstands how to operate at
Stripe, we didn't haveindividual quotas until maybe I
left the company.
So and I was yeah.
Yeah.
So I think by the time I left,we had team quotas.
We were we were slowly gettingthere because it wasn't
(18:35):
necessarily a traditional salesteam, right?
And when I joined Linear, wehad our head of sales and one
salesperson.
And when we hired that onesalesperson, he had a quota from
new one.
So just things like that, whereI think having that structure
can be really helpful.
In other businesses where youdon't understand your business
model, you don't understand yourpricing.
(18:56):
And some of those things weretrue of Stripe at the time.
You're like, oh, maybe weshouldn't have a quota because I
don't want to incentivize thewrong behaviors and end up
screwing up the business, right?
Sophie Buonassisi (19:05):
Yeah.
Cristina Cordova (19:05):
But I think when you have a pretty firm
sense of what your costs are andwe're in in some ways
traditional SaaS, right?
Seat-based selling.
So it is a little bit morestructured and easier to
understand and easier to model.
So there are definitely lessonsI've taken away that have been
more of that shape.
But I would say that my biggestlesson historically has been
(19:27):
knowing that at the end of theday you're the the judge on
whether you're doing a good jobis do the founders want to keep
you around?
Like as as an executive leaderwho's hired for by founders and
works for founders.
Yeah.
And there have definitely beenexecutives I've worked with in
my career where I'm just like, Ijust don't think this person's
(19:48):
doing a great job.
And and then you realize thatthe reason they're still there
is because the founders lovethem, you know?
And so the founder will shufflethem around to different parts
of the org and different partsof the company, even though
they're not doing a great job,because they're well liked by
the founders, right?
Sophie Buonassisi (20:05):
Right.
Cristina Cordova (20:05):
And so I hope that I'm doing actually a good
job, right?
Yeah.
Of course, that's the numberone goal.
But in reality, I think youhave to realize that a lot of
these decisions are relationshiporiented.
Um, who stays at a company, whogrows at a company, who gets
the opportunity to kind of seeit through for a long period of
time.
And I think what I've learnedis just like you have to build
(20:26):
those relationships so that youare on the same page and that
your understanding of what theirpriorities are and their
priorities should be yourpriorities.
And I think that's a criticalcomponent of success when you
think about being an executiveleader who's hired by founders.
Like, my job is to make theirlives easier and better.
(20:49):
And I would hope that at anypoint they say, I'm so thankful
we hired Christina because Idon't have to do this anymore,
or because now this is going somuch better, or all of these
things.
I want that to be true, butit's not going to be true unless
I invest in the relationshipand I understand what they want.
Sophie Buonassisi (21:06):
Yeah.
Absolutely.
That makes sense.
And let's say you're droppedinto a company who is very early
stage, similar to how you builtlinear, notion, stripe.
How do you assess thego-to-market?
Like what what would be thefirst things that you'd build
out just objectively,irregardless of the nuances of
the business?
But templates, frameworks,different ways of really
(21:28):
building out the go-to-marketroadmap.
Cristina Cordova (21:31):
I feel like I I would probably start with just
getting in there and being veryhands-on.
Yeah.
So are there are there salescalls I can join?
How do I get in front ofcustomers?
How do I observe what's goingon?
Right.
Yeah.
So really starting tounderstand those things, I
think, is is helpful.
You know, one of the firstthings I did at and one company
(21:53):
I joined was like I did a ridealong with our first
salesperson.
And I was like, can you like Iwasn't in sales, but I was like,
I just want to see the pitchand understand what this is like
and I can have aninterpretation on whether this
is good or bad, right?
Yeah.
And then we can figure out howto kind of make progress.
So I I think a lot of it isjust observational to kind of
understand things.
(22:14):
Like when I came into Linear,we had a head of sales, he was
our one salesperson.
Yeah.
Um, so he was both trying tobuild out the function and and
be an AE at the same time.
And we talked a lot about howhe wanted to build out the team
and hire more people.
But was feeling maybe like in asimilar way to how Stripe was
(22:34):
some resistance to hiringsalespeople from the founders.
Sophie Buonassisi (22:37):
Yeah.
Cristina Cordova (22:37):
Very normal.
And so it's trying tounderstand how does everybody
feel about this, right?
So talking to founders andunderstanding how do you think
it's going.
Sophie Buonassisi (22:46):
Yeah.
Cristina Cordova (22:46):
Right.
You may not actually know,right?
Because you're you're maybepotentially far removed from it,
but what is actually going onhere.
And then being in some of thosemeetings and calls and
understanding how they're goingyourself.
And then trying to match whatis the interpretation that other
people have about thisfunction, and then what is your
interpretation of theperformance at the ground level
(23:08):
with customers.
And I really care about thatfirst and foremost, because I
just I I would never want anyoneto have a bad experience.
And I think as an executive,there are so many times when bad
experiences are escalated toyou.
Oh, there were so many timeswhen I was at other companies
where it would be like, I hadthis terrible experience with
support.
Christina, can you help me?
(23:29):
Or things like that.
And that's probably the mostfrustrating moment operationally
as a leader when thoseescalations are coming to you
and you know that it is yourfault as the company.
So I think trying to understandthat at ground level is like
the first thing that'simportant.
You can tell the difference between someone
who's good and someone who'sgreat if you are exceptional at
something yourself.
You are better at kind oftrying to spot that
exceptionalism in other people.
Sophie Buonassisi (00:12):
You've scaled from less than 40 people
to thousands of people inorganizations.
And you've seen billion dollarsgo to market and you've seen it
built from scratch.
Listeners replayed what camenext more than any other moment
in the full episode withChristina Cordova, Strike's 20th
employee early leader atNotion, and now the COO of
Linear.
What you're about to listen tois that segment.
(00:33):
She outlines her framework ofstrategies for identifying
exceptional people early andevaluating the team's worth
betting on.
Hope you enjoy it.
And if you do, could you do mea favor and subscribe if you're
not already?
Thank you.
Appreciate you.
It helps us continue to bringon the guests and cover the
content that you're most excitedto hear about.
All right, let's get into it.
Other things that you look for,other than being whisked away
(01:06):
in a plane up top and anairline, but overall
curiosities, it sounds likeinvesting in long-term durabil
solutions.
Are there other things you lookfor?
Cristina Cordova (01:17):
Um so I would just say like talented in in
lots of ways that I am not.
It's part of it.
Yeah, exactly.
It's like I want a foundingteam to have a lot of skills
that they can bring to thetable, but skills that I can
(01:37):
observe are not my skills, but Ican still understand that it's
exceptional.
There are people that you canobserve and you're just like, oh
yeah, that's an engineer.
And and and and then whenyou've been working in this
industry long enough, you cantell the difference, even if
you're not an engineer betweensomeone who's good and someone
who's great.
And sometimes that might be indomains that are outside of what
(01:59):
you would think, like anengineer interacting with a
customer and try trying tounderstand their technical
feedback and how to fix it.
Sophie Buonassisi (02:06):
Yeah.
Cristina Cordova (02:07):
Um that's an interaction that you can observe
as someone who's notnecessarily technical to
understand if they're trulygreat at what they do.
So there's a lot that I thinkabout when I think about
founders, where it's okay, ifyou're a designer, I want you to
be one of the best designers inthe world.
If you're an engineer, I wantyou to be one of the best
(02:29):
engineers in the world.
And I think it's important thatas founders, you are bringing
the best of the best to thetable because it also helps you
recruit so many other reallyfantastic people too, because
you know what to look for assomeone who's great in whatever
domain that might be.
And then at the same time, Ithink in a lot of ways, you are
(02:52):
looking for exceptional peopleeven in other domains that you
are not familiar with.
So, you know, as an early stagecompany, you do a lot of first
of hiring.
You're hiring your first peopleops person and your first
recruiter and your firstsalesperson.
And as a technical founder, youmay not know a lot about those
domains or understand what's thedifference between good and
(03:14):
great.
But I tend to find that if youare exceptional at something
yourself, you are better at kindof trying to spot that
exceptionalism in other people.
So that's definitely a keycomponent of it.
And then I would say from abusiness standpoint as a whole,
I've generally joined companiesthat are post-having some kind
(03:36):
of product in the market.
Sophie Buonassisi (03:38):
Yeah.
Cristina Cordova (03:38):
So I try to look for a lot of signs that
that product is doing well inthe market.
It doesn't have to be doingamazingly well, right?
And also your interpretation ofthat on the outside is limited
given the data that you have.
But I love products that peoplelove so much that they want to
talk about them somewhere on theinternet, right?
(04:00):
So with Stripe, it was likepeople talking about Stripe on
Hacker News, and I would searchfor people posting about it and
what are people saying, right?
Because I'm also, I was not acustomer of Stripe.
I don't know, is this really agreat product, right?
So I would go talk to peoplethat I knew who were early stage
startup people, and I wouldsay, What are you using for
(04:22):
payments?
Oh, you're using Stripe.
Why did you choose that?
Do you like it?
You know, like those kinds ofthings to try and understand why
they made certain decisions.
Sophie Buonassisi (04:31):
Yeah.
Cristina Cordova (04:32):
And then for Notion, a lot of my perspective
was on Twitter, like, what arepeople saying about this
product, right?
Do they like it?
Do they love it?
Is it controversial?
You know, why?
Linear was very similar.
Like, where can I find thisproduct's audience?
And then what is the audiencesaying about the product?
Sophie Buonassisi (04:49):
Yeah.
Cristina Cordova (04:49):
Um, and I think that can be very helpful
to understand is this a belovedproduct?
Even if the audience is small,right?
And that matters a lot to mebecause, you know, for the most
part, you know, I've I've I'vemanaged literally every type of
function engineering, productmanagement, business, revenue,
all these things, but generallyI am not hands-on building the
(05:13):
product.
And so I would love to see thatthere's evidence that the
people who are hands-on buildingthe product are listening to
customers, know what customerswant, and that whatever they
have built so far is resonatingwith those customers.
And then I think what you tendto see is that people who are
maybe detractors or don'tbelieve in the brand might just
be bigger companies, right?
(05:34):
That are, oh yeah, like Stripe,that's for startups.
You know, that's what peoplewould say in the early days when
they were like, yeah, that'sprobably not going anywhere.
And then you realize that likeevery company starts out with
some kind of wedge in the marketthat they're focused on.
And then eventually over time,if they're successful, they're
(05:56):
able to kind of grow that wedgeand own a bigger share of the
pie.
Um, and for every company I'vebeen part of that's done B2B,
it's been starting with startupsin early stage companies and
then going to gross stagecompanies in mid-market and then
going to enterprise.
Right.
So, yes, the enterprisecompanies really early on are
gonna be like, oh, you're you'resmall, no one's gonna use you,
(06:20):
like that kind of thing.
And then you you're just gonnachange that company's mind.
And it might take you a decade,but you can do it, right?
Yeah.
But you should be resonatingreally well within that wedge
that you have defined is workingreally well.
So those are the things I tryto like suss out.
It's really people and like, isthe product resonating in the
(06:41):
market that you are reallyfocused on at this particular
moment in time?
But sometimes obviously whenyou're looking at a pre-product
company, it's really just theteam.
Yeah.
And that's all you've got,right?
And so figuring out what arethe data points that you do have
and do you find that thecompany is exceptional in one of
team market product areas.
(07:03):
Um and ideally it's all threeand you have a transformational
business in front of you.
Sophie Buonassisi (07:10):
So super cool.
It's really interesting to hearyou actually articulate that
because it mirrors exactly howwe evaluate startups too and
founders.
It really is, you know, two ofthe core areas I heard you stay
was around the person.
We think about that asspikiness.
Yeah.
You know, one of the founderswe invested in was the largest
creator of a Minecraft server.
Super niche and random.
(07:31):
But he was so passionate aboutthis idea that he pursued it.
Same kind of thing of you know,what are people excellent at
and what are they pursuing?
And then similarly with thebeloved customers and just
people being being huge ravingfans of a product.
We look for, you know, peoplethat would essentially be so
unhappy if the product was takenaway from them.
(07:52):
We'd look at that over revenueany day.
Cristina Cordova (07:54):
Yeah.
Sophie Buonassisi (07:54):
Or most days, I shouldn't say any day.
But most days, you know, we'drather have 10 happy design
partners that are paying a tiny,tiny fraction over, you know,
$500,000 in revenue if they'remore disparate logos sometimes.
Yeah.
That's kind of the sameprinciples I heard you say.
Cristina Cordova (08:08):
Yeah, I like what you mentioned around the
Minecraft thing.
It's like, to me, it's like I Iwant to see someone who's
exceptional at something becausethen I know that like when they
make this transition to being afounder, they're gonna want to
be exceptional at that too.
Right.
So whether it's craft or Idon't know, taekwondo, or your
IMO gold, or but those are themore classic, closer to
(08:31):
engineering type things.
Sophie Buonassisi (08:32):
But I didn't know Taekwondo was so
engineering.
Cristina Cordova (08:37):
So that more the IMO gold folks, but or those
people who do like, what is it,like quiz bull or things like
that, right?
Um these like competition mathystyle things, probably closer
to engineering and then maybegood founder, like you know,
you'll see.
But you want people to be goodat something.
That's what we're trying to do.
We're we're trying to buildsomething exceptional.
(08:57):
So having someone who's beenexceptional at something,
whatever it might be, is also areally good sign.
Like you see this even aboutsales leaders.
So many of them are athletes atcollege-level athletes go going
straight into sales.
And it's like, well, yeah, ifyou are someone who's who has
experience trying to get out andlike college athletics, you're
(09:19):
probably gonna be able to pickup the phone, make a lot of
phone calls, yeah, be relativelypersonable, and close some
deals, right?
Uh projection.
Right, exactly.
So things that where you'rejust kind of like, what's the
corollary for what this personhas done historically?
And does that translate to thisnew field?
Whether it's being a founder orbeing an operational leader or
(09:40):
what have you, you know, I thinkthe the interesting thing about
startups is that we're alldoing things that we have no
business doing.
I've never been a COO untilnow.
So, you know, you could arguewhat business do I have doing
this job, right?
I I had never worked at astartup, you know, until I had.
Yeah.
So we're all doing thesethings, I think, for the first
time.
And anyone who's building acompany is building a company in
(10:03):
that specific market for thespecific customer, you know, for
the very first time.
So we're all doing somethingthat we don't necessarily have
experience in.
And it's important to thinkabout A, what are the things
that I do bring to the tablethat are gonna help me adjust to
this problem and and how tosolve it?
And then are there examplesthat exist elsewhere that I can
(10:27):
learn from?
Um, I think the StripeFounders, one of the things
they're really great at, is justbringing in this growth mindset
to everything that they'redoing.
There were times when we weredoing company planning early on,
and they were like, Christina,could you maybe go off and have
some conversations with someother people at bigger companies
(10:47):
about how they do planning andthen bring those learnings back
to us.
Yeah.
Um, and so I went and I didthat and I talked to execs at
Amazon, at Meta, at Google,several places, and tried to
understand how they did planningand then what, if anything,
could translate to Stripe of 500people, I think at the time.
Right.
And at the same time realizingthat Stripe was a very first
(11:09):
principles-oriented company thatwasn't just gonna say, Oh,
well, Google plans this way, sowe should plan this way too.
Because, you know, is that whatmakes Google a great business,
how they do operationalplanning?
I I don't know, but it may notbe, right?
Right.
Or it could be unique to themin a certain way.
Right, yeah.
And so, like, is is the fitthere for your business, like
(11:32):
from this advice that you'regetting, and trying to
understand if it really appliesto you, and then understanding
is what makes this businessgreat, like this particular
thing, or actually, is it theseother things that they're really
good at?
And the operational planningcould be terrible, and it
wouldn't really matter.
Right.
Sophie Buonassisi (11:49):
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(12:32):
Very cool.
And what about the operatorside?
Because you yourself, you'vebeen, I mean, one of the first
business hires for companiesmultiple times.
You assess founders in acertain framework, like we
talked about.
Does the same framework applyto operators when you hire?
Because I've heard you say bethe person that builds without
being asked to.
Cristina Cordova (12:52):
Yeah.
I mean, I think it depends,like if you're if you're talking
about like leadershipspecifically, so some kind of
like operational leader within acompany.
I definitely think I've alwaysappreciated people who have a
more like entrepreneurialmindset.
So founder mode obviously beinga thing, but I I don't think
that solely applies to founders.
(13:14):
I definitely think it appliesto people who are leading in
companies.
And I think that's because themode that it requires of you at
a certain stage in size, whichis a like I have never joined a
company outside of my first jobat straight out of college with
more than 40 people, right?
So I've I've always been veryattracted to companies of a
(13:36):
certain style size and growingwith them over time.
Stripe was 3,000 people when Ileft.
But I think in a lot of ways,starting with companies that are
really small, you're lookingfor people who can see problems
and want to fix them, or see anopportunity and want to go out
and get it.
And I think for a lot ofpeople, maybe in more
(13:57):
traditional environments, arewaiting to be told what to do
and are waiting to be like, oh,what strategy is like, you know,
Christina gonna give me thattells me what I should do this
month.
And it's like, no, no, no, no,I'm hiring you because I think
you can come up with a strategy,right?
Um and you know, the differencebetween a really great
(14:18):
leadership hire and a not sogreat leadership hire is someone
who's coming to you and saying,Hey, you know, Christina, I
think we should change pricingat linear, right?
Or I think we should build outour AMIA team, or I think we
should do this.
And I'm like, this is a greatidea.
Let's have a conversation aboutit, right?
Yeah.
Versus me having to go to themand and necessarily say all of
(14:41):
those things.
Of course, there are going tobe things that I have ideas
about, and that's why I washired, right?
And and bring that to thetable.
But I but I do think I expectthat leaders that I hire are
going to not just think aboutwhat are the things that sh we
should be doing at certainstages or size of business.
Because there are there arethings that are pretty normal.
(15:03):
Like, okay, at this stage weshould start having audited
financials and we should get afinance person and we should,
you know, uh that's veryclassic.
Not necessarily like innovativeor going to transform the
business, though, right?
Yeah.
So if you're gonna spend time,you know, coming up with ideas,
I'd rather it be on the ladderrather than like on the stuff
that yes, we're gonna have to dothat at some point, and
(15:24):
reasonable, like, yes, we can dothat now.
Yeah.
But coming and saying, what arethe things that we're going to
do that can markedly change, youknow, the trajectory of what
we're doing, I think is reallyimportant.
And hiring people that youthink can do that.
But that's not true of allfunctions.
Some functions, like the job isto keep the lights on and keep
things moving and trains runningon time and things like that,
(15:45):
right?
True.
But I would say that for a lotof roles where you can make a
transformative impact for thebusiness, the job of leadership
is to really think through howthat business can transform and
then have the power to go andexecute against it.
Because ideas are great.
We all have lots of ideas, butif you can't execute and get it
(16:08):
done, the ideas don't goanywhere.
And so for me, I've always beena much more execution-oriented
person.
I really like doing things, Ilike getting things done, I like
making progress, but that can'tcome at the cost of thinking
strategically and trying to donew things and being innovative.
Sophie Buonassisi (16:27):
Yeah.
That makes sense.
And I mean, you mentionedyou've scaled from less than 40
people to thousands of peopleand organizations, and you've
seen billion dollar go to marketand you've seen it built from
scratch.
What are you doing now atLanier that you're restarting
that build process?
Cristina Cordova (16:45):
I think there are definitely lessons I've
learned.
Like in at Stripe at the earlydays, I think there was a lot of
fear of salespeople.
Like, as if the salespersonthat we would hire would be the
person who's trying to sell yousomething that you don't need
and all those kinds of things.
And it was like you can findsalespeople who who know sales
(17:07):
and can do it well withoutcoming across in this particular
way.
For sure.
And and so realizing that atearly stage companies the vibes
are important.
And if the founders suss outthat we're hiring salespeople
with the wrong vibes, it's notgoing to work.
Um, but knowing that I'd rathersave us a lot of time.
And instead of hiring peoplewho don't necessarily have sales
(17:27):
experience, hire people who areexperienced in sales, but have
done a lot of technical selling.
So selling to a buyer who is inengineering, product, and
design.
And we almost exclusively hiresalespeople with those
backgrounds, specificallybecause I I know that they have
to come across in a certain wayto not be salesy traditionally.
(17:52):
And that has saved us a lot oftime that I think was wasted,
you know, at at Stripe to kindof figure out, you know, how do
we sell?
What is the strategy here?
What is the approach?
And cut through some of thatinitial work and get straight to
what is the value that we'reproviding and how do we talk
(18:15):
about it, and what is the salesnarrative.
And then finding a team thatunderstands how to operate at
Stripe, we didn't haveindividual quotas until maybe I
left the company.
So and I was yeah.
Yeah.
So I think by the time I left,we had team quotas.
We were we were slowly gettingthere because it wasn't
(18:35):
necessarily a traditional salesteam, right?
And when I joined Linear, wehad our head of sales and one
salesperson.
And when we hired that onesalesperson, he had a quota from
new one.
So just things like that, whereI think having that structure
can be really helpful.
In other businesses where youdon't understand your business
model, you don't understand yourpricing.
(18:56):
And some of those things weretrue of Stripe at the time.
You're like, oh, maybe weshouldn't have a quota because I
don't want to incentivize thewrong behaviors and end up
screwing up the business, right?
Sophie Buonassisi (19:05):
Yeah.
Cristina Cordova (19:05):
But I think when you have a pretty firm
sense of what your costs are andwe're in in some ways
traditional SaaS, right?
Seat-based selling.
So it is a little bit morestructured and easier to
understand and easier to model.
So there are definitely lessonsI've taken away that have been
more of that shape.
But I would say that my biggestlesson historically has been
(19:27):
knowing that at the end of theday you're the the judge on
whether you're doing a good jobis do the founders want to keep
you around?
Like as as an executive leaderwho's hired for by founders and
works for founders.
Yeah.
And there have definitely beenexecutives I've worked with in
my career where I'm just like, Ijust don't think this person's
(19:48):
doing a great job.
And and then you realize thatthe reason they're still there
is because the founders lovethem, you know?
And so the founder will shufflethem around to different parts
of the org and different partsof the company, even though
they're not doing a great job,because they're well liked by
the founders, right?
Sophie Buonassisi (20:05):
Right.
Cristina Cordova (20:05):
And so I hope that I'm doing actually a good
job, right?
Yeah.
Of course, that's the numberone goal.
But in reality, I think youhave to realize that a lot of
these decisions are relationshiporiented.
Um, who stays at a company, whogrows at a company, who gets
the opportunity to kind of seeit through for a long period of
time.
And I think what I've learnedis just like you have to build
(20:26):
those relationships so that youare on the same page and that
your understanding of what theirpriorities are and their
priorities should be yourpriorities.
And I think that's a criticalcomponent of success when you
think about being an executiveleader who's hired by founders.
Like, my job is to make theirlives easier and better.
(20:49):
And I would hope that at anypoint they say, I'm so thankful
we hired Christina because Idon't have to do this anymore,
or because now this is going somuch better, or all of these
things.
I want that to be true, butit's not going to be true unless
I invest in the relationshipand I understand what they want.
Sophie Buonassisi (21:06):
Yeah.
Absolutely.
That makes sense.
And let's say you're droppedinto a company who is very early
stage, similar to how you builtlinear, notion, stripe.
How do you assess thego-to-market?
Like what what would be thefirst things that you'd build
out just objectively,irregardless of the nuances of
the business?
But templates, frameworks,different ways of really
(21:28):
building out the go-to-marketroadmap.
Cristina Cordova (21:31):
I feel like I I would probably start with just
getting in there and being veryhands-on.
Yeah.
So are there are there salescalls I can join?
How do I get in front ofcustomers?
How do I observe what's goingon?
Right.
Yeah.
So really starting tounderstand those things, I
think, is is helpful.
You know, one of the firstthings I did at and one company
(21:53):
I joined was like I did a ridealong with our first
salesperson.
And I was like, can you like Iwasn't in sales, but I was like,
I just want to see the pitchand understand what this is like
and I can have aninterpretation on whether this
is good or bad, right?
Yeah.
And then we can figure out howto kind of make progress.
So I I think a lot of it isjust observational to kind of
understand things.
(22:14):
Like when I came into Linear,we had a head of sales, he was
our one salesperson.
Yeah.
Um, so he was both trying tobuild out the function and and
be an AE at the same time.
And we talked a lot about howhe wanted to build out the team
and hire more people.
But was feeling maybe like in asimilar way to how Stripe was
(22:34):
some resistance to hiringsalespeople from the founders.
Sophie Buonassisi (22:37):
Yeah.
Cristina Cordova (22:37):
Very normal.
And so it's trying tounderstand how does everybody
feel about this, right?
So talking to founders andunderstanding how do you think
it's going.
Sophie Buonassisi (22:46):
Yeah.
Cristina Cordova (22:46):
Right.
You may not actually know,right?
Because you're you're maybepotentially far removed from it,
but what is actually going onhere.
And then being in some of thosemeetings and calls and
understanding how they're goingyourself.
And then trying to match whatis the interpretation that other
people have about thisfunction, and then what is your
interpretation of theperformance at the ground level
(23:08):
with customers.
And I really care about thatfirst and foremost, because I
just I I would never want anyoneto have a bad experience.
And I think as an executive,there are so many times when bad
experiences are escalated toyou.
Oh, there were so many timeswhen I was at other companies
where it would be like, I hadthis terrible experience with
support.
Christina, can you help me?
(23:29):
Or things like that.
And that's probably the mostfrustrating moment operationally
as a leader when thoseescalations are coming to you
and you know that it is yourfault as the company.
So I think trying to understandthat at ground level is like
the first thing that'simportant.
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