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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 episode
- 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
Episode highlights
00:00 — The difference between good and great—and how to spot it across functions
Watch: https://www.youtube.com/watch?v=HhOBzo0AlOk&t=0
00:12 — Why this clip hit: Cristina’s framework for identifying exceptional people early
Watch: https://www.youtube.com/watch?v=HhOBzo0AlOk&t=12
01:17 — Looking for skills you don’t have—and recognizing greatness outside your lane
Watch: https://www.youtube.com/watch?v=HhOBzo0AlOk&t=77
03:38 — Evidence a product is beloved (Stripe on Hacker News, Notion on Twitter)
Watch: https://www.youtube.com/watch?v=HhOBzo0AlOk&t=218
04:49 — Start with a wedge; win big later (why early enterprise skeptics don’t matter)
Watch: https://www.youtube.com/watch?v=HhOBzo0AlOk&t=289
07:54 — “Spikiness” and unconventional signals of excellence (Minecraft servers to sales)
Watch: https://www.youtube.com/watch?v=HhOBzo0AlOk&t=474
12:52 — What great early leaders do: see problems, create strategy, then execute
Watch: https://www.youtube.com/watch?v=HhOBzo0AlOk&t=772
16:45 — Sales at product-led companies: hire technical sellers, set quotas sooner
Watch: https://www.youtube.com/watch?v=HhOBzo0AlOk&t=1005
21:31 — How Cristina assesses GTM on day one: ride-alongs, direct customer observation
Watch: https://www.youtube.com/watch?v=HhOBzo0AlOk&t=1291
Key Takeaways
1. Be great at one thing first.
Exceptional founders usually have a prior spike (athletics, engineering, community building) that predicts how they’ll attack company-building with the same intensity.
2. Evidence beats opinions.
Early on you won’t have clean metrics, so hunt for proof of love in the wild (forums, social, user threads) and pressure-test it with customer calls.
3. Hire for complementary spikes.
World-class teams stack non-overlapping strengths; founders should deliberately recruit excellence in areas they don’t personally excel in.
4. Start with a wedge.
Don’t fear being “for startups” or a niche: own one beachhead deeply, then expand methodically into mid-market and enterprise.
5. Look for founder-mode operators.
Great early leaders don’t wait for a strategy memo; they propose it, get buy-in, and run – then bring back learnings fast.
6. Technical buyers need technical sellers.
If your users are EPD, prioritize salespeople fluent in product value, not just process; you’ll shorten cycles and keep “the right vibes.”
7. Quotas can clarify earlier than you think.
In clearer SaaS models, quota discipline from day one sets expectations and reveals gaps faster than vague team goals.
8. Relationships drive exec outcomes.
Founders decide who stays and scales: align on priorities, remove burdens for them, and invest in trust to earn the right to keep building.
9. Observe before you optimize.
Ride-alongs, raw call reviews, and escalations reveal reality faster than dashboards; fix the worst user experiences first.
10. Borrow, then adapt.
Steal planning patterns from bigger companies, but run them through first-principles: only keep what fits your stage, culture, and model.
This episode is brought to you by our sponsor: BoomPop
We’re deep in event planning right now, as no doubt many of you are.
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They handle everything from venues to experiences, so you can focus on the delights of meeting in person, not the logistics.
Being part of GTMnow, you’re eligible for full-service event planning for just $99 per person (terms apply). Head to boompop.com/gtmfund to explore seamless support for your events.
Follow Cristina Cordova
- LinkedIn: https://www.linkedin.com/in/cristinajcordova
- X (Twitter): https://x.com/cjC
Referenced
- Linear: https://linear.app/Linear
- Linear About: https://linear.app/aboutLinear
- Notion:https://www.notion.com/Notion
- Stripe:https://stripe.com/Stripe
- BoomPop:https://boompop.com/BoomPop
Host links
- LinkedIn: https://www.linkedin.com/in/sophiebuonassisi
- Website: https://gtmnow.com/
- Newsletter: https://thegtmnewsletter.substack.com
Where to Find GTMnow
- Website: https://gtmnow.com
- LinkedIn: https://www.linkedin.com/company/gtmnow
- X (Twitter): https://x.com/GTMnow_
- YouTube: https://www.youtube.com/@GTM_now
- Podcast Directory: https://gtmnow.com/tag/podcast
GTMnow Bonus Episode Transcript
Cristina Cordova: 0:00
You can tell the difference between someone who’s good and someone who’s great if you are exceptional at something yourself. You are better at kind of trying to spot that exceptionalism in other people.
Sophie Buonassisi: 0:12
You’ve scaled from less than 40 people to thousands of people in organizations. And you’ve seen billion dollars go to market and you’ve seen it built from scratch. Listeners replayed what came next more than any other moment in the full episode with Christina Cordova, Strike’s 20th employee early leader at Notion, and now the COO of Linear. What you’re about to listen to is that segment. She outlines her framework of strategies for identifying exceptional people early and evaluating the team’s worth betting on. Hope you enjoy it. And if you do, could you do me a favor and subscribe if you’re not already? Thank you. Appreciate you. It helps us continue to bring on the guests and cover the content that you’re most excited to hear about. All right, let’s get into it. Other things that you look for, other than being whisked away in a plane up top and an airline, but overall curiosities, it sounds like investing in long-term durabil solutions. Are there other things you look for?
Cristina Cordova: 1:17
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 founding team to have a lot of skills that they can bring to the table, but skills that I can observe are not my skills, but I can still understand that it’s exceptional. There are people that you can observe and you’re just like, oh yeah, that’s an engineer. And and and and then when you’ve been working in this industry long enough, you can tell the difference, even if you’re not an engineer between someone who’s good and someone who’s great. And sometimes that might be in domains that are outside of what you would think, like an engineer interacting with a customer and try trying to understand their technical feedback and how to fix it.
Sophie Buonassisi: 2:06
Yeah.
Cristina Cordova: 2:07
Um that’s an interaction that you can observe as someone who’s not necessarily technical to understand if they’re truly great at what they do. So there’s a lot that I think about when I think about founders, where it’s okay, if you’re a designer, I want you to be one of the best designers in the world. If you’re an engineer, I want you to be one of the best engineers in the world. And I think it’s important that as founders, you are bringing the best of the best to the table because it also helps you recruit so many other really fantastic people too, because you know what to look for as someone who’s great in whatever domain that might be. And then at the same time, I think in a lot of ways, you are looking for exceptional people even in other domains that you are not familiar with. So, you know, as an early stage company, you do a lot of first of hiring. You’re hiring your first people ops person and your first recruiter and your first salesperson. And as a technical founder, you may not know a lot about those domains or understand what’s the difference between good and great. But I tend to find that if you are exceptional at something yourself, you are better at kind of trying to spot that exceptionalism in other people. So that’s definitely a key component of it. And then I would say from a business standpoint as a whole, I’ve generally joined companies that are post-having some kind of product in the market.
Sophie Buonassisi: 3:38
Yeah.
Cristina Cordova: 3:38
So I try to look for a lot of signs that that product is doing well in the market. It doesn’t have to be doing amazingly well, right? And also your interpretation of that on the outside is limited given the data that you have. But I love products that people love so much that they want to talk about them somewhere on the internet, right? So with Stripe, it was like people talking about Stripe on Hacker News, and I would search for people posting about it and what are people saying, right? Because I’m also, I was not a customer of Stripe. I don’t know, is this really a great product, right? So I would go talk to people that I knew who were early stage startup people, and I would say, What are you using for payments? Oh, you’re using Stripe. Why did you choose that? Do you like it? You know, like those kinds of things to try and understand why they made certain decisions.
Sophie Buonassisi: 4:31
Yeah.
Cristina Cordova: 4:32
And then for Notion, a lot of my perspective was on Twitter, like, what are people 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 this product’s audience? And then what is the audience saying about the product?
Sophie Buonassisi: 4:49
Yeah.
Cristina Cordova: 4:49
Um, and I think that can be very helpful to understand is this a beloved product? Even if the audience is small, right? And that matters a lot to me because, you know, for the most part, you know, I’ve I’ve I’ve managed literally every type of function engineering, product management, business, revenue, all these things, but generally I am not hands-on building the product. And so I would love to see that there’s evidence that the people who are hands-on building the product are listening to customers, know what customers want, and that whatever they have built so far is resonating with those customers. And then I think what you tend to see is that people who are maybe detractors or don’t believe in the brand might just be bigger companies, right? That are, oh yeah, like Stripe, that’s for startups. You know, that’s what people would say in the early days when they were like, yeah, that’s probably not going anywhere. And then you realize that like every company starts out with some kind of wedge in the market that they’re focused on. And then eventually over time, if they’re successful, they’re able to kind of grow that wedge and own a bigger share of the pie. Um, and for every company I’ve been part of that’s done B2B, it’s been starting with startups in early stage companies and then going to gross stage companies in mid-market and then going to enterprise. Right. So, yes, the enterprise companies really early on are gonna be like, oh, you’re you’re small, no one’s gonna use you, like that kind of thing. And then you you’re just gonna change that company’s mind. And it might take you a decade, but you can do it, right? Yeah. But you should be resonating really well within that wedge that you have defined is working really well. So those are the things I try to like suss out. It’s really people and like, is the product resonating in the market that you are really focused on at this particular moment in time? But sometimes obviously when you’re looking at a pre-product company, it’s really just the team. Yeah. And that’s all you’ve got, right? And so figuring out what are the data points that you do have and do you find that the company is exceptional in one of team market product areas. Um and ideally it’s all three and you have a transformational business in front of you.
Sophie Buonassisi: 7:10
So super cool. It’s really interesting to hear you actually articulate that because it mirrors exactly how we evaluate startups too and founders. It really is, you know, two of the core areas I heard you stay was around the person. We think about that as spikiness. Yeah. You know, one of the founders we invested in was the largest creator of a Minecraft server. Super niche and random. But he was so passionate about this 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 the beloved customers and just people being being huge raving fans of a product. We look for, you know, people that would essentially be so unhappy if the product was taken away from them. We’d look at that over revenue any day.
Cristina Cordova: 7:54
Yeah.
Sophie Buonassisi: 7:54
Or most days, I shouldn’t say any day. But most days, you know, we’d rather have 10 happy design partners that are paying a tiny, tiny fraction over, you know, $500,000 in revenue if they’re more disparate logos sometimes. Yeah. That’s kind of the same principles I heard you say.
Cristina Cordova: 8:08
Yeah, I like what you mentioned around the Minecraft thing. It’s like, to me, it’s like I I want to see someone who’s exceptional at something because then I know that like when they make this transition to being a founder, they’re gonna want to be exceptional at that too. Right. So whether it’s craft or I don’t know, taekwondo, or your IMO gold, or but those are the more classic, closer to engineering type things.
Sophie Buonassisi: 8:32
But I didn’t know Taekwondo was so engineering.
Cristina Cordova: 8:37
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 mathy style things, probably closer to engineering and then maybe good founder, like you know, you’ll see. But you want people to be good at something. That’s what we’re trying to do. We’re we’re trying to build something exceptional. So having someone who’s been exceptional at something, whatever it might be, is also a really good sign. Like you see this even about sales leaders. So many of them are athletes at college-level athletes go going straight into sales. And it’s like, well, yeah, if you are someone who’s who has experience trying to get out and like college athletics, you’re probably gonna be able to pick up the phone, make a lot of phone calls, yeah, be relatively personable, and close some deals, right? Uh projection. Right, exactly. So things that where you’re just kind of like, what’s the corollary for what this person has done historically? And does that translate to this new field? Whether it’s being a founder or being an operational leader or what have you, you know, I think the the interesting thing about startups is that we’re all doing things that we have no business doing. I’ve never been a COO until now. So, you know, you could argue what business do I have doing this job, right? I I had never worked at a startup, you know, until I had. Yeah. So we’re all doing these things, I think, for the first time. And anyone who’s building a company is building a company in that specific market for the specific customer, you know, for the very first time. So we’re all doing something that we don’t necessarily have experience in. And it’s important to think about A, what are the things that I do bring to the table that are gonna help me adjust to this problem and and how to solve it? And then are there examples that exist elsewhere that I can learn from? Um, I think the Stripe Founders, one of the things they’re really great at, is just bringing in this growth mindset to everything that they’re doing. There were times when we were doing company planning early on, and they were like, Christina, could you maybe go off and have some conversations with some other people at bigger companies about how they do planning and then bring those learnings back to us. Yeah. Um, and so I went and I did that and I talked to execs at Amazon, at Meta, at Google, several places, and tried to understand how they did planning and then what, if anything, could translate to Stripe of 500 people, I think at the time. Right. And at the same time realizing that Stripe was a very first principles-oriented company that wasn’t just gonna say, Oh, well, Google plans this way, so we should plan this way too. Because, you know, is that what makes Google a great business, how they do operational planning? I I don’t know, but it may not be, right? Right. Or it could be unique to them in a certain way. Right, yeah. And so, like, is is the fit there for your business, like from this advice that you’re getting, and trying to understand if it really applies to you, and then understanding is what makes this business great, like this particular thing, or actually, is it these other things that they’re really good at? And the operational planning could be terrible, and it wouldn’t really matter. Right.
Sophie Buonassisi: 11:49
So quick pause because it’s event season and this is a game changer. At GTM Fund, our portfolio companies, our LP operators companies, we’re all planning events right now, as I’m sure you are. Sales kickoffs for next year, company retreats, conferences, you name it. It’s a lot of work. Planning these company events has been made simple though, with Boom Pop’s AI powered platform and event planners. They handle everything from venues to experiences, so you can create an incredible event without being bogged down by the planning process itself. And as a listener of GTM Now, you’re eligible for an exclusive discount, full service event planning for just $99 per person. Terms and details are on the webpage in the show notes, which is boompop.com forward slash GTM fund. Head there to start planning your next offset. Very cool. And what about the operator side? Because you yourself, you’ve been, I mean, one of the first business hires for companies multiple times. You assess founders in a certain framework, like we talked about. Does the same framework apply to operators when you hire? Because I’ve heard you say be the 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 leadership specifically, so some kind of like operational leader within a company. I definitely think I’ve always appreciated people who have a more like entrepreneurial mindset. So founder mode obviously being a thing, but I I don’t think that solely applies to founders. I definitely think it applies to people who are leading in companies. And I think that’s because the mode that it requires of you at a certain stage in size, which is a like I have never joined a company outside of my first job at straight out of college with more than 40 people, right? So I’ve I’ve always been very attracted to companies of a certain style size and growing with them over time. Stripe was 3,000 people when I left. But I think in a lot of ways, starting with companies that are really small, you’re looking for people who can see problems and want to fix them, or see an opportunity and want to go out and get it. And I think for a lot of people, maybe in more traditional environments, are waiting to be told what to do and are waiting to be like, oh, what strategy is like, you know, Christina gonna give me that tells 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 difference between a really great leadership hire and a not so great leadership hire is someone who’s coming to you and saying, Hey, you know, Christina, I think we should change pricing at linear, right? Or I think we should build out our AMIA team, or I think we should do this. And I’m like, this is a great idea. Let’s have a conversation about it, right? Yeah. Versus me having to go to them and and necessarily say all of those things. Of course, there are going to be things that I have ideas about, and that’s why I was hired, right? And and bring that to the table. But I but I do think I expect that leaders that I hire are going to not just think about what are the things that sh we should be doing at certain stages or size of business. Because there are there are things that are pretty normal. Like, okay, at this stage we should start having audited financials and we should get a finance person and we should, you know, uh that’s very classic. Not necessarily like innovative or 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 ladder rather than like on the stuff that yes, we’re gonna have to do that at some point, and reasonable, like, yes, we can do that now. Yeah. But coming and saying, what are the things that we’re going to do that can markedly change, you know, the trajectory of what we’re doing, I think is really important. And hiring people that you think can do that. But that’s not true of all functions. Some functions, like the job is to keep the lights on and keep things moving and trains running on time and things like that, right? True. But I would say that for a lot of roles where you can make a transformative impact for the business, the job of leadership is to really think through how that business can transform and then have the power to go and execute against it. Because ideas are great. We all have lots of ideas, but if you can’t execute and get it done, the ideas don’t go anywhere. And so for me, I’ve always been a much more execution-oriented person. I really like doing things, I like getting things done, I like making progress, but that can’t come at the cost of thinking strategically and trying to do new things and being innovative.
Sophie Buonassisi: 16:27
Yeah. That makes sense. And I mean, you mentioned you’ve scaled from less than 40 people to thousands of people and organizations, and you’ve seen billion dollar go to market and you’ve seen it built from scratch. What are you doing now at Lanier 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 early days, I think there was a lot of fear of salespeople. Like, as if the salesperson that we would hire would be the person who’s trying to sell you something that you don’t need and all those kinds of things. And it was like you can find salespeople who who know sales and can do it well without coming across in this particular way. For sure. And and so realizing that at early stage companies the vibes are important. And if the founders suss out that we’re hiring salespeople with the wrong vibes, it’s not going to work. Um, but knowing that I’d rather save us a lot of time. And instead of hiring people who don’t necessarily have sales experience, hire people who are experienced in sales, but have done a lot of technical selling. So selling to a buyer who is in engineering, product, and design. And we almost exclusively hire salespeople with those backgrounds, specifically because I I know that they have to come across in a certain way to not be salesy traditionally. And that has saved us a lot of time that I think was wasted, you know, at at Stripe to kind of figure out, you know, how do we sell? What is the strategy here? What is the approach? And cut through some of that initial work and get straight to what is the value that we’re providing and how do we talk about it, and what is the sales narrative. And then finding a team that understands how to operate at Stripe, we didn’t have individual 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 getting there because it wasn’t necessarily a traditional sales team, right? And when I joined Linear, we had our head of sales and one salesperson. And when we hired that one salesperson, he had a quota from new one. So just things like that, where I think having that structure can be really helpful. In other businesses where you don’t understand your business model, you don’t understand your pricing. And some of those things were true of Stripe at the time. You’re like, oh, maybe we shouldn’t have a quota because I don’t want to incentivize the wrong 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 and we’re in in some ways traditional SaaS, right? Seat-based selling. So it is a little bit more structured and easier to understand and easier to model. So there are definitely lessons I’ve taken away that have been more of that shape. But I would say that my biggest lesson historically has been knowing that at the end of the day you’re the the judge on whether you’re doing a good job is do the founders want to keep you around? Like as as an executive leader who’s hired for by founders and works for founders. Yeah. And there have definitely been executives I’ve worked with in my career where I’m just like, I just don’t think this person’s doing a great job. And and then you realize that the reason they’re still there is because the founders love them, you know? And so the founder will shuffle them around to different parts of the org and different parts of 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 number one goal. But in reality, I think you have to realize that a lot of these decisions are relationship oriented. Um, who stays at a company, who grows at a company, who gets the opportunity to kind of see it through for a long period of time. And I think what I’ve learned is just like you have to build those relationships so that you are on the same page and that your understanding of what their priorities are and their priorities should be your priorities. And I think that’s a critical component of success when you think about being an executive leader who’s hired by founders. Like, my job is to make their lives easier and better. And I would hope that at any point they say, I’m so thankful we hired Christina because I don’t have to do this anymore, or because now this is going so much better, or all of these things. I want that to be true, but it’s not going to be true unless I invest in the relationship and I understand what they want.
Sophie Buonassisi: 21:06
Yeah. Absolutely. That makes sense. And let’s say you’re dropped into a company who is very early stage, similar to how you built linear, notion, stripe. How do you assess the go-to-market? Like what what would be the first things that you’d build out just objectively, irregardless of the nuances of the business? But templates, frameworks, different ways of really building out the go-to-market roadmap.
Cristina Cordova: 21:31
I feel like I I would probably start with just getting in there and being very hands-on. Yeah. So are there are there sales calls I can join? How do I get in front of customers? How do I observe what’s going on? Right. Yeah. So really starting to understand those things, I think, is is helpful. You know, one of the first things I did at and one company I joined was like I did a ride along with our first salesperson. And I was like, can you like I wasn’t in sales, but I was like, I just want to see the pitch and understand what this is like and I can have an interpretation on whether this is good or bad, right? Yeah. And then we can figure out how to kind of make progress. So I I think a lot of it is just observational to kind of understand things. Like when I came into Linear, we had a head of sales, he was our one salesperson. Yeah. Um, so he was both trying to build out the function and and be an AE at the same time. And we talked a lot about how he wanted to build out the team and hire more people. But was feeling maybe like in a similar way to how Stripe was some resistance to hiring salespeople from the founders.
Sophie Buonassisi: 22:37
Yeah.
Cristina Cordova: 22:37
Very normal. And so it’s trying to understand how does everybody feel about this, right? So talking to founders and understanding 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 maybe potentially far removed from it, but what is actually going on here. And then being in some of those meetings and calls and understanding how they’re going yourself. And then trying to match what is the interpretation that other people have about this function, and then what is your interpretation of the performance at the ground level with customers. And I really care about that first and foremost, because I just I I would never want anyone to have a bad experience. And I think as an executive, there are so many times when bad experiences are escalated to you. Oh, there were so many times when I was at other companies where it would be like, I had this terrible experience with support. Christina, can you help me? Or things like that. And that’s probably the most frustrating moment operationally as a leader when those escalations are coming to you and you know that it is your fault as the company. So I think trying to understand that at ground level is like the first thing that’s important.
