How Figma Scaled From $2M to IPO | Kyle Parrish (First Sales Hire)

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Kyle Parrish joined Figma as the first-ever sales hire when the company was doing $2M in ARR and helped scale it to $950M ARR. Figma then went on to IPO (FIG).

But the path there was anything but smooth.

In this episode, Kyle breaks down what it actually took to build Figma’s enterprise sales motion from scratch, including the no-discount rule that made procurement teams furious, the 40-hour interview weeks when hiring felt impossible to keep up with, and what it was like to lead a 300-person team through a failed $20B Adobe acquisition, and then have their best year immediately after.

Discussed in this episode

Why Figma refused to discount, even when Microsoft pushed back
How to hire the right first sales rep as a founder
The PLG to enterprise transition most companies get wrong
What the Adobe deal collapse actually felt like from the inside
How Figma went from 3 products to 8 overnight and launched into an IPO
What great sales looks like in the AI era

Episode highlights

0:00 – Intro

1:02 – Guest intro: Kyle Parrish

1:35 – Joining Figma at $2M ARR in 2018

5:01 – First meeting with Dylan (Figma CEO)

6:13 – How to find your first sales hire

9:05 – Stage alignment in early hiring

11:43 – Early-stage operators need “scar tissue”

13:19 – Northstar metric at Figma

14:13 – Obsessing over customer conversations

16:44 – Building Figma’s brand through community

17:31 – Scaling the “unscalable”

20:08 – In-person GTM vs. digital

22:47 – Was there a moment Figma might not make it?

24:48 – Pivoting after the Adobe deal collapsed

28:10 – Figma’s no-discount rule

31:05 – Enterprise ELAs replacing discounting

34:47 – What makes a great salesperson in the AI era

36:56 – Missionaries vs. mercenaries in AI-era GTM

39:47 – Spotting the next Dropbox or Figma

43:46 – Kyle’s post-Figma investing focus

45:58 – Family, travel & what’s next

Key takeaways

1. Stage alignment is everything when hiring your first sales rep.
Don’t bring in a big-company executive to an early-stage role. You need someone addicted to building, comfortable with ambiguity, and willing to do 15 jobs badly before figuring out which ones matter. The wrong hire at this stage can set your entire GTM culture back by years.

2. Figma’s no-discount rule was a trust play, not a pricing play.
By staying consistent across every customer, Figma built a reputation for transparency that became a competitive advantage. It was painful early, especially with enterprise procurement, but it forced the team to win on value instead of price.

3. PLG only works if your sales team respects the community it’s selling into.
Figma’s early sales motion was built on genuine curiosity, not quotas. Kyle and his team sat on couches with designers for hours, went to meetups, and learned the world they were selling into. That relationship with the community is what made the enterprise motion possible.

4. The Adobe acquisition collapse was Figma’s biggest unlock.
Being under a potential acquisition froze Figma’s ambition. The moment the deal died, the product team was unleashed, Dev Mode launched, and the company went from 3 products to 8 in a single conference. The $1B breakup fee funded the best chapter of Figma’s story.

5. In the AI era, sales fundamentals matter more, not less.
AI removes the excuse for poor preparation, but it puts an even sharper spotlight on how you build trust, do discovery, and show up in person. The sellers thriving right now are leaning into AI as a tool while doubling down on the human skills that no model can replace.

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GTM 187 Episode Transcript

00:00 – 00:01

Sophie: Kyle. What can we teach him now?

00:01 – 00:03

Kyle: Yeah. Thank you for having me.

00:03 – 00:25

Sophie: Absolutely. It’s great to have you here. And, I want to start off here because Figma is now a publicly traded company trading under the ticker name Figg. And you were the first ever sales hire at Figma. So starting with that. Now, you joined in 2018. But Figma had actually existed for about six years prior to joining without making a dollar revenue.

00:25 – 00:35

Sophie: So take us back to the beginning when you actually joined Figma. At that time, what was the state of the company? What were you joining to do? Love to just transport you back to that moment.

00:35 – 00:52

Kyle: Yeah, I mean, it’s interesting, I think for anyone that’s looking for trends and, to be honest, if I knew I was going to be as big as the companies became, I would have been static. But there’s kind of three core trends that drew me to the company in the first place. So when I was, you know, five years plus at Dropbox, starting to think about what I wanted to do next.

00:52 – 01:11

Kyle: There’s a couple things happened in Silicon Valley during that time. Call it, you know, 2013 to 2015. You were seeing massive companies going at these huge markets. And just like growing like crazy with a focus on design. Part of that was brand design, but a big part of it was UI and UX companies like Square and Twitter and Uber and Airbnb.

01:11 – 01:28

Kyle: You know, we all know these companies and we think of how their products are extremely intuitive and allow them to reach users and customers by the masses. And the same thing was happening at Dropbox, like we had these designers that were prolific designers, folks like Silvio, you know, who is a design leader at Facebook and then the like button.

01:28 – 01:49

Kyle: And Rasmus was the first employee at Spotify who later actually went over to Figma as well. But they’re joining Dropbox and kind of creating these, like, headline news. And so everyone in the company knew them. Cloud storage on its own. Right. No one’s saying I love cloud storage. But we would see people in the airport, you know, back in the heyday of Dropbox, and they’d say, see my shirt and say, I love Dropbox, right?

01:49 – 02:03

Kyle: It evoked emotion. And a big part of that was the focus on design. And so that was the first thing was like it was just hard to ignore. I think the second part was I was working with a lot of product leaders and design leaders. They wanted to hear from the sales team, how are we going to customers?

02:03 – 02:25

Kyle: What are the roadblocks we’re hitting? Sales team also want to know what was the roadmap, what are the things that are coming down the line? And even as late as 2015, early 2016 when I left the company, it was crazy how static it was. It was like, here’s a mock up of what we’re building. Let’s go show it to a group of, you know, 100 plus salespeople, get their feedback and then run that same cycle 6 to 8 weeks on the line.

02:25 – 02:46

Kyle: And it was just kind of broken. And the core of what we were selling at Dropbox was really collaboration. And so the last kind of third thing that led me to Figma was I was early enough, I joined as the 50th employee at Dropbox and the third sales hire. So I got to meet a lot of the engineers and you know, really engineers, product design folks, there was all kind of core part of the team is very little commercial people at that time.

02:46 – 03:04

Kyle: Yeah. And some of the new grad engineers were breaking off on Dropbox is still, you know, growing and still a great place to be and work. And they had gone to Brown Wood Dillon and have been the co-founders of Figma. And I was like, that’s interesting. Like these, you know, two engineers that are very respected to Dropbox are like going to this company Figma.

03:04 – 03:19

Kyle: And I’m like design collaborative. But it was like very you didn’t know exactly what they’re building. There was like a healthy amount of buzz, but also a long time of like not making money and kind of being in that stealth period. I think Dylan did a really good job of spending a lot of time with everyone across Silicon Valley.

03:19 – 03:33

Kyle: So he was very well known. And so I actually sent a note to the recruiter. They had one recruit at the time. I was like, this looks really interesting. Let me know when you’re thinking of building out the business team. Didn’t hear back. I ended up taking a sabbatical to travel with my wife for a year. And don’t regret that.

03:33 – 03:51

Kyle: When I came back, I first met Dylan in 2017 via the former head of talent at Greylock. This guy, Dan Porthos, a friend and mentor of mine. And when I first met Dylan, like a lot of companies, I think self-serve. They were probably the first time I met him doing 500 K in revenue, credit card kind of online trade process stuff.

03:51 – 04:07

Kyle: So we’re self-serve or self-serve. I’m not sure if we’re ready for sales. And I was like, totally fair. And we just kind of kept in touch. And then, they called me back in 2018, I came, spent a lot of time with them. The CFO at the time, our head of finance, who I worked with previously, is the CFO now.

04:07 – 04:24

Kyle: Purveyor. And yeah, they had 4 or 5 customers in beta. They were doing, just under 2 million in their hour before I joined, basically 2 million when I joined. And they want to start to build out like a customer facing motion. And they wanted to launch the product in the next kind of 6 to 12 months, more formally.

04:24 – 04:44

Kyle: And so that was it. It was like nobody really customer facing. Support was a huge part of, I think, interactions with customers. And it’s a really important of the business part of the business today. Yeah. From there, I was like, the target was to start to build this kind of enterprise business side of the house.

04:44 – 05:04

Sophie: I love it. Well what a journey to start there. Pretty much at 2 million RR. And I think the first sales hire is one of the most critical but also the most challenging roles to hire for as a founder or as an early stage company. I know we ourselves and fun. We are constantly having these conversations and supporting portfolio companies across not Critical Hire.

05:04 – 05:19

Sophie: So as your advising companies now and at the time, obviously being a first sales hire and a third sales hire at Dropbox to how would you advise founders to find the right for sales hire? Like how do they find the Kyles?

05:19 – 05:56

Kyle: Yeah, it’s a good question. I think partially you have to kind of have conviction on if you want to bring in a leader, someone who’s lead and is going to kind of start to like build and scale the function. You know, Dropbox, I grew up in Dropbox in so many ways. I think I joined the company was 24 and almost six years there. One of the strongest network of people that I’ve met. They’re just remarkable professionally. Like, absolutely brilliant, kind human beings and turn into these amazing friendships and relationships that still last today. And when I joined, it was pre-series B announcement, and little did I know, it was my first startup and we were just going to go in this Hypergrowth journey.

05:56 – 06:15

Kyle: And so you learned a lot about maybe what to do and also what not to do, which I think is really important. And so I think, being one of the kind of OGs of this PG motion, there’s a little different in that it was consumer and enterprise and Sigma’s business is more prosumer like. Everyone’s using it in a professional way and enterprise.

06:15 – 06:36

Kyle: Yeah. There’s just like a lot of playbooks that I was able to kind of come in and apply. And I was the first person promoting the leadership on the team, and by the time I left had led a pretty large team, you know, 100% team at Dropbox. So being able to like, get that exposure, cut my teeth allowed me to come in, but also not be scared and be kind of stage aligned to come in and have no playbook, no resources and built from scratch.

06:37 – 06:54

Kyle: Like I was kind of addicted to the building and, you know, still always am. I may be doing it by way of advising and investing in companies today. But yeah, I met two candidates they were talking to and met them like over a coffee and a beer, respectively. And I hadn’t even joined the company, didn’t fully know the culture, but I was like, sure.

06:54 – 07:12

Kyle: They seemed like, you know, good potential adds to the team. We hired those two people, and it was the three of us for the first six months. And a lot of the core focus was like just really understanding, why people were thinking about like using the product of Figma, how they’d use it in a more kind of scalable enterprise fashion.

07:12 – 07:37

Kyle: And who are the people that are actually driving this behavior? You have a lot of these end users that are really passionate about the tool. Does that mean they’re going to get really large companies to, like, use it and sign up for it? And I think one of the concerns that I had that was a little bit, you know, just unknown at the time, really, was it going to be a little bit more of bring your own tool kind of environment, and you’d have some parts of the organization that were using Sketch and Invision and other tools, and some parts were using Figma.

07:37 – 07:55

Kyle: But I think the way that we, solve problems for really large companies with design systems and distributing that over the browser, it allowed us to start with small teams in that kind of land and expand motion and then expand pretty aggressively from there. So, when you’re looking for someone like that, I think it has to be stage aligned.

07:55 – 08:16

Kyle: I always tell people, like, a lot of people want, you know, when it goes well and you’re part of a company that hopefully goes public or gets acquired and you have this great exit and you’ve built a big team and there’s a lot to be proud of. That looks really appealing. But you have to go back to the early days when it’s not glamorous, when you’re doing one of 15 jobs and kind of failing at a lot of them.

08:16 – 08:42

Kyle: As time goes, you’re paying part enablement, part sales finance. You’re the manager, you’re the rep. You’re doing everything just to kind of learn what is going to define the foundation of the culture, for working with customers. Ultimately driving revenue. And then as you start to really hire and kind of, increase the complexity, you’ve got a decent blueprint of what that looks like.

08:42 – 08:58

Kyle: And so, I think a lot of founders, if they’re not quite ready to bring in a leader and maybe scale to a team of five or greater, they bring in a lot of like, you know, you know, this title, a lot of like founding eight years. Yeah, I think that’s really great. And that’s probably grown a lot more in the last 5 to 7 years.

08:58 – 09:11

Kyle: I don’t think that you want to bring in someone like me or even someone like me in 2018, unless you feel like there’s conviction that we can have a ten person team by the end of the year or early next year. That was what I was most interested in doing. I think that was whereas most valuable as well.

09:11 – 09:27

Kyle: And I think a lot of the like handoff from founder led sales can be bringing in your first 2 or 3 reps. And that’s a lot of research. You know, it’s a lot of selling, a lot of customer facing activity. It’s also a lot of research to try to find product market fit versus we’re pretty confident we found product market fit.

09:27 – 09:35

Kyle: Now let’s bring in the right leader. Give them the opportunity, the responsibility to grow into the role of what this can become.

09:35 – 09:41

Sophie: So match the stage and then match whatever that conviction is or stage or act to.

09:41 – 10:20

Kyle: Yeah. I mean, to this day I think I’ll talk to, you know, one of the things I try and bring is like my lens as a, as an operator who also advises and invest in early stage startups is that, you know, they have a lot of respect for what I’ve been a part of and what I’ve been, you know, I have a chance to help build. And so I think some investors will be like, oh, go get that executive that worked at that big publicly traded company and bring them into your series, A company, you know, you’re doing 3 million or 5 million in revenue. And sometimes that can work out. But more than not, unless that person is shown somewhere on their resumé, in their experience across their track record, that they’ve been in early stage where it’s all about prioritizing and you don’t have all these resources and tools.

10:20 – 10:37

Kyle: It’s not. This goes sit in your command center and twist knobs. Yeah, it’s let’s go do and let’s go figure it out and solve and create these really, really tight feedback loops. And you have to work really close engineering really close with product. Of course, the executive team, the founder, all these people because you’re figuring it out. Yeah.

10:37 – 10:50

Kyle: And they’re building it and they’re shipping and you’re launching and it’s all these things that are happening at such a fast pace that that’s not for everyone. And I think a lot of people have these like, startup dreams and then they go do it and they’re like, Holy shit, you know, that’s hard.

10:50 – 10:56

Sophie: Yeah, yeah. And it’s a lot of juggling. So you find the people with a little bit of scar tissue from having done it before.

10:56 – 11:14

Kyle: Like, I’m not an entrepreneur. I’ll never say that. You know, I am, but I think that the early stage team, these people are builders by nature, and they’re drawn to kind of the messiness. And they’re not scared by ambiguity. They kind of want to come in and build and figure it out. And it’s hard. And some days like, this is sucks and I feel like I’m going to fail.

11:14 – 11:33

Kyle: But when things start to click and things start to work and you bring in people and you share the workload with more incredible people, and you bring in people that have an area of expertise that kind of complements your background and allows you to kind of uplevel think in a longer, more strategic lens. You know, that’s when it gets really fun and really dynamic.

11:33 – 11:51

Sophie: Very, very. And Kristen. Yeah. And he was, the very first sales hire at snowflake. He came on GTM. Now, one of the things that he said was he was obsessed in the early days with talking to customers. So he had this one goal, and it was eight customer conversations per week. That was his Northstar. And he did that every single week.

11:51 – 11:59

Sophie: When he joined as the first sales hire. Did you similarly have some kind of Northstar metric that you were just obsessed with when you first joined Figma?

11:59 – 12:25

Kyle: Yeah, we didn’t have a number, but I think that we were lucky because we had this kind of volume that was growing as we were going and people using the core product. Yeah. So my first year and a half was the pre-COVID era, right? And so we had so many amazing companies. I’m here based in San Francisco. And so we were just like up and down the peninsula doing on sites, flying to New York, you know, with Dylan, we went and, you know, New York Times, we were at the peak of their heyday.

12:25 – 12:48

Kyle: Ido, the design agency, some of the biggest companies world, Google, all these people that, you know, customers of Figma and have been for many, many years. And so I think we were obsessed with talking as many customers we could documenting, because when I came in, there wasn’t a lot of documentation of talking to customers and hearing through more of a sales customer first lens of like, what was the problem you’re looking to solve?

12:48 – 13:02

Kyle: What are the challenges your organization like? How are you thinking about the future of design and thinking? Part of me was for learning. You know, I’ve been around designers and working designers, but I hadn’t, like in the design field, and there wasn’t a lot of people that have sold and been the go to market in the design world.

13:02 – 13:21

Kyle: So for us, we just this relentless focusing on getting in front of people. And I think it was really, really cool and unique. The VP of design is still there today. Noah. Nico, who’s like a legendary designer who was in the early, show who was the first manager. And he’s done a million things. He’s been there for over ten years at Figma.

13:21 – 13:39

Kyle: All these people would join the sales team and had no egos, just wanted to get in front of customers. And it wasn’t just pure like, let’s go sell it. Let’s understand where they’re coming from. And I think that connection and the way that we approached it was really unique. I think when when Dylan hired me, there was a lot of pressure to build in a good way.

13:39 – 14:01

Kyle: And this is what was what excited me as well to build a sales culture that connected with our audience. When you have an amazing plg business and it’s starting to like, you know, take off and have these grass roots, the community is such a big part of that. And so being able to find a go to market motion that leverages that community learns from them and grows with them is really important.

14:01 – 14:20

Kyle: If you come in here and you just try and rinse and repeat the challenger sales model in the design world, it’s probably not going to work. And so it was just a lot of spending time with these people in person. And then we go to lunch and we talk to them. And you know, I felt like at Dropbox I was close to the customers, but nothing like Figma, like I made like, true friends.

14:20 – 14:33

Kyle: Brian Haggerty, one of the leaders at Twitter, you know, he came and just sat on a couch with me for three hours, and it was part like, hey, I’m the new head of sales for this company. And so, like, we’d love to sell your software. Of course. Yeah. But also I’d love to just learn from you.

14:33 – 14:56

Kyle: And they were just so open, so generous with their time and kind of just, like, rooting for someone to go and win in this space. And so, yeah, there was always like, we were pushing really hard, but there was a healthy pull from the community of like, can there be a new company that really understands us, builds for us, and kind of sees the future in the same way that we do?

14:56 – 15:21

Sophie: 100%. And I mean, I think there are a few companies that have the same visceral kind of reaction than customers do around Figma. The admiration for Figma as a brand is tremendous. And you know Sheila Vashi who’s the current CMO and actually I believe Sheila. Yeah. You got that will drop boxes. She was the second marketing hire you were that the marketing hires. You’re really scaling in early stages together now. Yeah. Figma also I.

15:21 – 15:22

Kyle: Didn’t you know.

15:22 – 15:43

Sophie: Then yes. Reunited there and she talks a lot. She talked a lot about brand and just how these, like, really tight feedback loops, like you said, just unscalable things like sitting on a couch for three hours or, you know, Dylan flying to visit customers abroad that were really, like the central tenants to how you scaled information in these feedback loops internally at Figma.

15:43 – 15:50

Sophie: How did you actually scale that long term as a sales team just as you grew? Because that is it’s hard to scale the Unscalable.

15:50 – 01:03:22

Kyle: Yeah. And again, like part of it, we would do a lot of customer on sites like being in person. And the other thing that we did a lot in the first couple of years is, there’s a meetup to design meetups that were really popular. And so they’re pretty popular. But like pre-COVID, it was like a huge thing.

16:04 – 16:26

Kyle: And so there’s an opportunity to go to these meetups, and sometimes we would sponsor them or just be like loosely involved, just come and hang out and kind of be like, I work at Figma, and there’s enough buzz and curiosity around what we were doing to engage these people. But, I mean, there’s this massive community doing events all over the world, and then, like someone from Figma would show up or Dillon would show up and a member of the sales team, members of the community, team marketing team, designer, advocates.

16:27 – 16:45

Kyle: And yeah, it’s just a huge opportunity to, like, tap into this community. And I think if you come with the approach of, like, we’re here to sell you something, right? Like that’s obviously going to be off putting. But I think, everyone from stemming from Dylan Wright, really, and his curiosity and passion for the space, it was all like, we just really want to understand the state of the world as you see it.

16:45 – 17:06

Kyle: We’re building this company. There’s a strong point of view around what the product could look like and should look like, but there’s also going to be a lot of, learning from the audience that we’re spending time with, like who we’re building for. I think they’re going to dictate the roadmap per se. But if you don’t really, really understand the persona and the ICP of the people that you’re selling to in serving, it makes it hard to like have the success that we had.

17:06 – 17:32

Kyle: So I think the Figma brand, kudos to everyone on the marketing team and the community. Team designer advocates huge part of success story. They’re just so, focused and curated around keeping that brand as is. It was small. It was easier right? As it got big and as it got global. And as you lead up to going public and you know, they the an amazing tagline design is everyone’s business in New York and on Wall Street.

17:32 – 17:51

Kyle: And it’s like it’s it’s real. And it’s, it’s a lot of work that goes into that. And so I’m the first person to say, you don’t have all the sales success we had without that focus on brand, that focus on community, and trying to learn to play with it and kind of learn from that community versus, disregard it.

17:51 – 17:56

Kyle: And just like, you know, go straight to, let’s killing revenue as fast as you possibly can.

17:56 – 18:20

Sophie: Totally. And we kind of see that now, particularly with AI, but across our portfolio is a lot of these on site visits, time spent with customers, not necessarily as a metric, but just how people are spending their time. But that is by far what’s most effective right now is just FaceTime in person, being with people, spending time to deeply understand their problems at scale.

18:20 – 18:33

Sophie: I’m curious if you’re seeing any kind of similar patterns across the companies that you’re advising. Or just as I kind of grows on the digital side, what that means for these kind of unscalable in person. Yeah. Connection.

18:33 – 18:52

Kyle: My take from talking to a lot of people that are still you know, in some of the fastest growing companies on the planet, former people on my team and just, you know, my community that have built of 20 years kind of, you know, being in this, this wild race is that in go to market, I don’t think as much is changed as opposed to like if you’re building product.

18:52 – 01:13:04

Kyle: I think a lot has changed. On the go to market side, I think there’s a lot of efficiencies. There’s a lot of things that you shouldn’t have to do. There’s no excuse for lack of preparation. Yeah. Knowing about your customer, there’s no excuse for knowing all the internal things that you need to do. But what it does is puts an even stronger focus on how you show up, how you build trust, how you do discovery.

19:13 – 19:30

Kyle: And I think in today’s age, right, coming out of the Covid era, there was this massive kind of void of spending time with customers, spending time with your colleagues. And so now, as we get back to this in-person world, I think it’s really, really powerful. But you also have a lot of people, especially sellers, that maybe grew up in this area, right, that are fast rising.

19:30 – 19:50

Kyle: They can be SMB, mid-market enterprise reps, and face to face or in person is new to them. You know, for many people of my era, we were fortunate. That’s all we knew for the first parts of our career. And then we did everything virtually. We do it or not. But if you just started out you were one year in in Covid hits, you’re kind of forced to now, in this era, figure out what that looks like.

19:51 – 20:09

Kyle: But I also think that people do it and it makes the job fun. I was just talking to like a crew of one of these companies, and it’s like it breaks up the day and week and you’re out there and you can see the work that you’re doing, you can see the impact the company is having. And when you come back from that trip, whether it’s road trip or you get on a plane or whatever it may be, it’s just really rewarding.

20:09 – 20:30

Kyle: It’s like it’s tangible. You know? And I think that, now there’s a lot more focus on salespeople being really, really good salespeople and not just kind of packing 14 zoom calls into a day and focus on a hyper efficiency. There was, you know, some part of that during Covid for some companies. But now I think it’s a lot of trust building, and there’s more and more startups than ever before.

20:30 – 20:44

Kyle: And so for these enterprise buyers are trying to figure out who are the companies I want to bet on who’s going to be around in 2 or 3 years. Yeah. And who understands me and wants to spend the time building and supporting me. In a way, it feels like a partnership and not just another vendor.

20:44 – 21:07

Sophie: 100%. Yeah. And one thing that a lot of early stage operators speak to, is the tumultuous kind of journey that it takes to go on to actually build and scale a company, as you did at Dropbox and Figma. I’m curious for Figma specifically, were any kind of moments along the journey that you weren’t sure if Figma would make it as a company?

21:07 – 21:52

Kyle: You know? Yeah, there were I mean, I think, for most of the like, let’s call it pre Adobe Growth era. We just didn’t have a lot of relative competition. You know, you have other constraints when you’re growing that fast. And I think being a PG company, you know, we didn’t come out always with the highest compensation when we started really moving up market and selling more in the enterprise. And just, you know, some weeks I do 40 hours of interviews before I even like jumping on one on ones or responding to emails and slack, because that was like the main focus of letting go of the team fast enough. Nothing else mattered. But yeah, I think, the Adobe era was hard. Yeah. People don’t realize you could do an acquisition period.

21:52 – 22:12

Kyle: It was also when there’s kind of this pullback of, of tech. So investing kind of slowed down a really big way. And our business was extremely predictable for so many years. And we would forecast very accurately, you know, across all regions globally. And then contraction started becoming a little bit more of a thing. And so you have to factor into that, which is that post 22 period.

22:12 – 22:36

Kyle: Meanwhile were under this like, you know, period of potential acquisition. Yeah. And there’s so much news and news cycles. My team was 300 plus people at that time. And so you’re trying to lead a team through uncertainty. In reality, we weren’t shipping and launching as ambitious stuff that we probably would have if we weren’t under that Adobe period, and kind of like, dotted line reporting to them and kind of like potentially joining their company.

22:36 – 22:51

Kyle: And so I don’t know that I thought that Figma was going to die was just that, that was tough. And then when you come out, there was a lot of questions on what is Figma go from here. Yeah. You know, what is their future? That deal just did they get $1 billion breakup fee. And you know, kudos to Dylan.

22:51 – 23:27

Kyle: Like we we just kind of pivoted on a dime. There was no time to sit and, kind of feel sad or whether you wanted it to happen or not. You spent all this time, you know, you could say, oh, is that a waste? Time was it not? Of course you get some capital as a part of it. We just put that energy into momentum and we launched one of these new products, Dev Mode, and just had this breakout year that completely inflected the growth rate in a in a great way. And we saw the sales team and the go to market teams kind of rally around that on the marketing side, on the sales side and on our advocate side, engineering and product was kind of unleashed and they were shipping and building.

23:27 – 23:49

Kyle: And then, you know, you were still hearing some of the same rumors leading up to last year’s config, which is the company’s annual conference. And the company basically went from having three products to eight products overnight. Just an absolute mic drop of like a, a ship and kind of, feature launch and of course, the IPO is, you know, magical, but like, it’s just a long road.

23:49 – 24:05

Kyle: And now the world is changing in a lot of ways. And so you just have to bet on Dylan, the executive team, which is phenomenal. All the amazing people that are still Figma and, just how strong the business we have. And I think we’re probably close to 100% of fortune 100 using Figma if not already there.

24:05 – 24:06

Sophie: Yes.

24:06 – 24:24

Kyle: And so I think people just under appreciate the relationships we have, the trust we have, and that the right way right to win. We have given that, you know, we have all the design and product data for what you’ve built in the last 6 or 7 years. But yeah, there’s no none of these journeys are as smooth as they look.

24:24 – 24:43

Kyle: Right? Like there’s always these rollercoaster moments. And that’s what I always tell people when you’re hiring ten years underrated because anyone that sailed any company, you know, and some have better outcomes and others you’ve shown resilience. You didn’t fold in when the going got tough because we had plenty of moments for myself, for folks on my team where the going gets tough.

24:43 – 24:49

Kyle: And that’s when you kind of like see the character of both yourself. And I think the teams you’re a part of as well.

24:49 – 24:59

Sophie: Absolutely. And just context for anyone listening who may not be familiar with the Adobe Deal two is Adobe announced, that they were going to acquire Figma in 2022 for 30 million.

24:59 – 25:00

Kyle: $20 billion.

25:00 – 25:21

Sophie: For $20 billion. And then that deal actually fell through in 2023. And so I can’t imagine that was an easy time to actually keep the team motivated. But it sounds like you guys just powered on ahead. And obviously the outcome was incredible. The IPO was at a high, far higher rate than the actual Adobe acquisition. Yes was intended to be.

25:21 – 25:40

Sophie: So that’s fantastic. And congratulations to you and everyone at Figma on the IPO. Yeah, Kyle Figma had a very unique structure with a no discount rule, which is a sales leader is quite an interesting thing to navigate. And I know you experienced pushback with Microsoft shareholder about this. No discount. Ross. Super curious.

25:40 – 26:23

Kyle: Yeah. It was one of those things where you walk in, and I had never worked at a company that didn’t have a discount kind of. Yeah, framework or policy. And I think a couple of things allowed us to do it. And it was unique. The first was that we have a lot of user types that didn’t monetize in the former kind of pricing model. They’ve changed the pricing model a little bit, in the past year. But we had viewers that got a ton of value, and that was a core part of the Figma platform. I think when people thought about the business of Figma and the market they were going after, there was questions around how big is that market? The reality is that the market of designers grew rapidly, and Figma agree with that, but also that one of my favorite stats early on was that we monetized, less than half of monetized users identified as designers.

26:23 – 26:41

Kyle: So you had people that were UX writers and people and product developers who were using the product and wanted full edit access, but also a lot of viewers that were going to never pay us for their usage, but could come in comment, be part of the digital development process and then, you know, kind of be considered for free.

26:41 – 27:00

Kyle: So I think it all came down to framing like we didn’t discount the perceived price, but then viewers get a lot of value for free. And so that was one part. I think you have to have a certain market in a, in a strong product to kind of do that, but it’s kind of you know, Dylan’s idea originally, we kind of went with it, and I think sales had to take it on the chin many times over.

27:00 – 27:21

Kyle: In those early days, because our whole pricing model with the initial, deal structure, the true ups, all of that, we kind of defined it in many ways. And so, yeah, it was a it was a lot to react to what I will say once the market got through and people started believing us, we only had Dylan join one call.

27:21 – 27:40

Kyle: Won’t say the customer, but, to kind of validate, hey, this is a real thing and we don’t discount our product because to be fair, once you get really high up in the enterprise, these procurement people want to bring back a win. And a big part of that win is the price per unit of what they’re paying for coming down as they invest and start to pay for 10,000 users or whatever it may be.

27:40 – 27:56

Kyle: And so when your structure doesn’t allow for that and they don’t feel like they’re getting, you know, price breaks for kind of investing you in a scaled way, it creates a lot of friction. But, I think is really good learning that comes from it. I think there’s more and more founders that are curious about it and want to try it out.

27:56 – 28:17

Kyle: One, you’re consistent across all of your customers. You know, once that kind of started to like, leak out into the community, ether people knew that we didn’t discount. We were consistent, we were transparent. And there’s kind of some, yeah, some trust that’s like built there. I think the second is that your sales people are less focused on, you know, there’s always the negotiation and trying to structure a deal.

28:17 – 28:46

Kyle: And I’ll kind of talk about how it evolved to where we didn’t discount, but the kind of deals that we did. But yeah, they take that out of their like tool bag a little bit. And so just like less of a focus and like I’m going to come in and discount, it’s more around doing really good discovery, understanding what these companies care about, the challenges you’re trying to problem is trying to trying to solve for the ROI case that you’re trying to build and then ultimately getting them to convert and deliver and like kind of proving true on that value versus like overly focused on like, I can get this deal done this month.

28:46 – 29:02

Kyle: I’m going to cut 30% in it. And so what we did ended up doing for the majority of our enterprise customers, they moved to Ella’s Enterprise level agreements. And so we would try to work with customers and we would work with our CFO and building this framework around. As we got more and more products, it got more complicated.

29:02 – 29:16

Kyle: So we’d have these dotted lines to the products that they were using, but we’d try and come up with a number that felt like, hey, we’re forecasting this amount of growth. Maybe you’ve been a customer for a year, maybe you’re brand new, or maybe you’ve been with us for 3 or 4 years. We came up with a number that they feel good about.

29:17 – 29:38

Kyle: We feel good about the sell side and on the growth side, and we kind of come to this like, you know, middle ground. Right. Last year contractors 300 K. We think you’re going to grow, add new products, use it closer to like 700 K next year. And that way as a buyer hopefully they see that right. If they exceeded their perceived value their kind of price per unit, decreases.

29:39 – 00:04:12

Kyle: And on our side activation engagements only going to fuel platform adoption and hopefully future future growth from there. And so it’s kind of like win win. I think for a lot of these buyers, they want that predictability. They want to be able to forecast their spend and they want to stay under their budget. I think a lot of this is, of course, changing the AI era where you kind of, you know, generally have these two pronged pricing models where it’s either a user base fee or platform fee and then some level of consumption. Yeah, I think procurement people are reacting and they’re starting to figure it out and they’re realizing this isn’t going away. But at first it’s probably an absolute nightmare, right? Because you have no idea how to how to forecast this stuff.

30:16 – 30:42

Sophie: Yeah. And so much is changing too with AI now just the pricing transparency across companies. It’s so easy for customers to actually do their research ahead of time and validate pricing across competitors. So do you think that kind of no discount model, something that applies to founders now, or was that an era of Figma? And it’s not necessarily something that founders are applying now though you said founders are curious about it.

30:42 – 31:00

Kyle: Yeah, I think it still applies. And I think not every company, if you’re in a really, really competitive market, you know, maybe you have to use discounting just to like, you know, have a slight edge, but I think less so that just is like buttoned up in today’s world where it’s like there’s kind of two parts of a pricing strategy and model.

31:00 – 31:20

Kyle: It’s more about coming up with a package that feels like the buyer has some predictability. It feels fair to them, and maybe it’s like a platform fee of, you know, 20% on the contract. And then the rest of it is some kind of consumption credits, API calls, whatever it is that you’re using on the AI side. And of course, there’s some value tied to what you’re doing.

31:20 – 31:44

Kyle: So they’re going to use more and more of the platform, effectively pay you more. And you’re paying one of these model companies more to feel the credits. They want to make sure that the returns there. Yeah. And I think they also want to make sure that’s really important for a lot of these tools, especially the ones that are really hitting scale, that they have some level of admin controls or killswitch, you know, we’ve all heard the stories on yeah, X or Twitter or it’s like engineer who spends $100,000 in one day on, you know.

31:44 – 32:03

Kyle: Yeah. And so I think if you’re in procurement and you’re trying to manage a budget, I mean, maybe there’s a ton of value that was generated from that 100 K day. Maybe, you know, there wasn’t. And so I think it’s less about we don’t discount I think it’s it could be like a, a core fundamental. But it’s about gives and gets with the customer.

32:03 – 32:22

Kyle: Like how do we build, a pricing structure and a pricing strategy that feels like as we go up market and there’s just generally more complexity in the AI era in terms of pricing. Like they feel like it’s a good deal. And for us, you know, we feel like we’re getting, you know, fairly compensated and can kind of run and grow our business sustainably.

32:22 – 32:37

Sophie: And another complexity of the AI era is actually around the individual sales people and the types of hires that you’re making. And you’ve spoken about this and the evolution. I would love to hear more of your thoughts around that, of what makes a good salesperson in the AI era.

32:37 – 32:55

Kyle: Yeah, I think, again, it goes back to a lot of the same fundamentals of what made a great salesperson in the in the SAS era a couple of years ago. I think that the core difference is that if you’re in the SAS era, maybe there is less innovation happening. You know, broadly across the world or in technology that you have to pay attention to.

32:55 – 33:10

Kyle: And I think now if you’re at one of these, forward leaning charging AI companies are starting to do really well as a sales rep, as a sales leader, and you’re not leaning into AI and how it’s going to transform your day to day, what the tools are that the company is adopting, you’re going to get left behind.

33:11 – 33:24

Kyle: And I think generally, you know, I lean on the optimist side of like, I was going to take all of our jobs or at least a lot of these jobs. And some of that may be true, but I think we’ll continue to just kind of as humans and humans in the loop, find where we fit around the tools and around the technology.

33:24 – 33:48

Kyle: And I think, from the companies I’m advising, investing and even the folks that I’ve worked with and hired in the past, the folks that are thriving in some of these, these breakout companies, they’re just leaning all in, like, how can I leverage this to be really, really good? Spend time on the weekends tinkering, building stuff? You know, one of the greatest unlocks in all of this is that now non-technical folks can build things.

33:48 – 33:48

Sophie: Truly.

33:48 – 34:13

Kyle: And they can support their day jobs. They can, you know, build little hobby apps or whatever it may be. Right. And so I think that, that’s the big thing, in addition to everything else you’re looking for, you’re looking for people that are structured and have a plan to their day are extremely resilient. Are able to, kind of understand the rigor that goes into being a really good salesperson, be able to connect with your customers, do discovery without it feeling like an interrogation.

34:13 – 34:31

Kyle: You know, all of those things. But an AI era, people are moving really, really fast. Companies are moving really, really fast, and you’re just not going to be relevant if you’re not spending time understanding what’s happening. And that’s like a full time job in itself. To be fair. Yeah. So I think, you know, people in these roles are just they’re they’re working around the clock.

34:31 – 34:32

Kyle: And that’s a big part of it.

34:33 – 35:00

Sophie: Yeah. People are working around the clock, I mean, for their roles. But I always think of now AI education as your career, not your job. Like if you’re not carving out that time, you might not have a career. Like, you just simply have to totally be on the job itself. And what are you seeing now from our go to market perspective, as I just call this such a disruption, but also not as much of a perhaps disruption like you mentioned before, for all the companies that you’re advising investing.

35:00 – 35:23

Kyle: Yeah, I think, there’s all these promises out of the gates, right? Like it’s always that first hype cycle. It’s going to be, you know, solved or delivered and it’s like, yeah, I SDR and all these promises. And that didn’t really come to fruition. You know, and there’s some questions of like in the AI era and a lot of automation and a lot of intelligence moving around like, you know, do some of these roles exist in the same capacity?

35:23 – 35:43

Kyle: Of course, like the the hottest term is forward deploy. And I’m a forward deployed and deployed GTM person and whatever. And so, you know, I think the, the nomenclatures and the naming of this stuff kind of changes and evolves. But, yeah, I think in the AI era, one thing that I’m seeing pretty consistently is like, it’s a little different than makeup.

35:43 – 36:01

Kyle: And I hear this from people as well. And these teams, I think when I was a part of Dropbox and Figma, we felt very like mission oriented and we kind of felt like missionaries. And at some point of scale, I think you sort of bring in people that are just pure executable mercenaries. I don’t love the name, but like, that’s kind of like this age old playbook, right?

36:01 – 36:20

Kyle: You get to this point. These people are less risk averse. They’re they’re purpose built for that stage. And they want to come in, have all the resources and go and do the job and perform and then do really well. I think now everything’s moving so fast and maybe some companies are like, maybe overshooting that whole what does it mean to be on this company?

36:20 – 36:40

Kyle: What is the culture that we’re defining? And I don’t mean, you know, the fluffy stuff of culture, you know, the free snacks and lunch and all those things. But like, how do you connect with the colleagues around you? How do you learn from these people? How do you make time to establish these real relationships and bonds so that as the going gets tough, which inevitably will for all of these companies?

36:40 – 36:57

Kyle: You know, there’s no perfect path in this world. They they have those kind of connection points, and it feels more of like a team versus we’re all just sprinting. And it may be a marathon, but we’re going to sprint in a sprinter’s pace. And I think there’s a lot of that. And it feels like that’s the way you have to operate.

36:57 – 37:20

Kyle: But at some point we’re going to hit the status quo. I’m not saying you won’t work less necessarily, but we realize that AI is here to stay, and we also want to work in a way that’s sustainable and that’s connected with their colleagues, going to their customers and just investing more in that versus, you know, just AI education and just cranking in your core job and not creating any time for those moments where you just get to spend and learn from those people around you.

37:22 – 37:46

Sophie: That’s that’s brilliant. Interesting. Very interesting to hear what you’re seeing, hearing there. And for a lot of us for a lot of operators, they are constantly looking to better understand the market and join companies that become the next Dropbox, that become the next Figma. And you always say it’s easy to recognize great in hindsight. But when you joined Dropbox when you joined Figma, they were early.

37:46 – 37:59

Sophie: They were super early. Yeah. So what are the patterns that you find and see in companies from Dropbox and Figma? And now how you’re picking companies when you’re investing that actually determines and predicts what great looks like and becomes.

37:59 – 38:17

Kyle: Yeah, I mean, the earlier you go, of course, the founder and the, the magnetism there. You know, that’s a big part of it. It’s like, do you think this is someone that has a strong moral compass? Do you think this person has this kind of compelling story and right to win? Building a company, going after this market?

38:17 – 38:39

Kyle: Like, why are they so fired up to go do this? I mean, you look at, the two companies I spent the majority of my career true house and still running Dropbox, you know, 20 years and Dylan, 13, 14 years into the post. That is a very intense job. And I think there’s this kind of concept of, serious founders and non serious founders in my, you know, almost 20 years of doing this.

38:39 – 38:40

Sophie: I think it goes to operators, to.

38:40 – 38:55

Kyle: Operators as well. Yeah. And I think in my 20 years of doing this, I’ve seen it go from being a founder as like this thing where like this, like burning desire to go do it. It was almost like this hard club to break into if you didn’t have such conviction to. It’s almost a bad thing to do in this day and age.

38:55 – 39:21

Kyle: Yeah, and of course, there’s a lot of fundraising. And so I think that’s a big part of it is like understanding the founder dynamic. Do you believe in this person? Do you want to work for them on their team and help them build, like in the trenches? Is that something that like it draws you in? And the other part, they say I couldn’t test a good or great engineer, but after spending so much of my early part of my career Dropbox, I know when I’m around them and I can kind of sense when it doesn’t feel like it’s top notch or high caliber.

39:21 – 39:43

Kyle: And so, you know, sometimes you’re always going to get that in interview process. But more and more as we’re going back into person going and office, like, you know, ask to meet someone on a technical team, hey, who’s building this products? Like, I think most hiring managers and founders find that interesting and curious. And you get a sense for like the caliber of these people, like what they’re thinking about, why they joined the company, why they’re excited because they come at it from a very different lens.

39:43 – 40:06

Kyle: It could be a technical challenge. It could be the opportunity to go after. It could be, you know, the space in which they’re building is so unique. It could be the team and how they saw it in different way because they’re technical and you have more of a commercial background. And then last but not least, I’ve always said this like, for me, I have to be interested and engage in like the space and the product I talked about, like what drew me to Figma in the early days with Dropbox.

40:06 – 40:23

Kyle: I’m old enough that, you know, I had a thumb drive all of college. Like, if I lost that, there goes my paper cooked. Yeah. And, I was actually in my first sales job. I started working in ADP right out of college. I was faxing in order forms. So, like 2010, I’m like faxing in order for them.

40:23 – 40:42

Kyle: So I’m like, Holy shit, this feels completely archaic. Yeah. So when I first used Dropbox, there’s this wow moment and I was just like, wow. Yeah. So then for me personally and professionally, I’m like, that was innovative. You know, cloud storage and having your data and your content across all of your devices and sync to the cloud, was like a big part of it.

40:42 – 41:04

Kyle: So those are the things you want to do. And then of course, if there is a team, if there’s a go to market team, if there’s a leader, is that person inspiring and motivating? Can you learn from them when you look at their career path, is it something you want to emulate? And I think, probably what I’m most proud of, of the Figma journey is just seeing all these people that came in at varying levels in their lives and careers and, you know, where they come out, whether they’re still Figma today or they’ve moved on.

41:04 – 41:16

Kyle: You know, leadership is not always a cakewalk, but it’s the impact and the influence and just being a part of the journey and learning from these people as well. I’ve learned as much them as they learned from me, and that’s kind of the beauty of it.

41:16 – 41:27

Sophie: That is beautiful. And now you’re advising your investing companies with your time. Post Figma. And what are you most excited about when you’re advising and investing or spaces that you’re looking at?

41:27 – 41:43

Kyle: Yeah, I invest in a lot of like dev tools, creative tooling, ends up being a lot of like infrastructures and GTM systems of record. I think I was talking about this earlier, but it’s almost more when I don’t invest in like I don’t do crypto, I don’t know, area of expertise there. I don’t do fintech or consumer.

41:43 – 42:10

Kyle: And so I think I been really nice with some of my background is because like, it’s opened up even more and more like I think if you’ve helped build sales teams and now as an advisor and investor, you’ve gotten really deep with the founders that you work with. Learn about a ton of different business models. I think just that’s one of the beauties of being in this kind of role right now is that as opposed to going really, really deep on that one company, I’m spending time in a lot of different areas, like different markets.

42:10 – 42:28

Kyle: And, yeah, I don’t know, I’m biased, but I think it’s like just a really interesting time to kind of see the market from this lens and kind of make some sense of it. And then when, you know, get to the advising stuff, it’s a little bit more hands on. I’m spending a lot of times with folks that are heads of sales, VP of revenue, cross these early stage companies.

42:28 – 42:45

Kyle: And, you know, I’ve had some journeys myself and they’re kind of going on one now. And so as it goes and it’s similar in leadership, some days you’re kind of advising them. Some days you’re, you know, therapist and some days you’re helping them kind of connect the dots and decisions they have to make that are hard and critical and time sensitive.

42:45 – 43:05

Kyle: So that’s what I’m excited about. And I think for me, just finding these, like, amazing investors like that or founders or like I said, who are just have this like magnet that’s pulling me towards them. And I believe that they’re going to build an exceptional company. They’re going to grow into an exceptional leader that that, you know, is managing teams and teams and teams.

43:05 – 43:33

Kyle: You know, you look at Dillon leading a 2000 person team, and he famously was an intern, you know, before starting Figma and then yeah. Lastly, like, is it a space where I can be evaluated and for my checks that I write at this angel investor, I joke around these founders like, I greatly try to outweigh the value that I bring to the table, you know, and and that’s the fun part is just getting into the weeds and, helping them kind of, you know, solve problems and grow their business.

43:33 – 43:42

Sophie: Absolutely. You’re also spending a lot of time with your, your family and, traveling lot traveling is one of your passions. Where’s next on the travel card?

43:43 – 44:04

Kyle: Well, well, we’re actually having our third kid this summer, so travel can be pretty light this year. Yeah. But, yeah, I mean, I’m pretty excited to also just kind of write down and spend time with my other two kids and get them all into the outdoors and doing a bunch this summer. If all goes well, you know, maybe we’ll go to Hawaii later this year and yeah, take the new baby out to the beach, do some surfing stuff of that nature.

44:04 – 44:18

Kyle: But, yeah, because of that, you know, a little less travel this year than last year. Last year, after leaving Figma, I was opportunity just, you know, travel with my young kids and get out there. And I’ve, had a little bit more freedom than I had the past seven years.

44:18 – 44:24

Sophie: Some well-deserved freedom. And I’m surprised we haven’t had some sales surfing analogies come out because you’re a pretty big surfer.

44:24 – 44:28

Kyle: Yeah, not a good one. But, you know, I’ve been doing it for a long time, but, that’s.

44:28 – 44:32

Sophie: Awesome for Kyle. This has been fantastic. Really appreciate the conversation. You joining?

44:32 – 44:34

Kyle: Thank you. Yeah. Thank you for having me. It’s a friendly meet.

44:34 – 44:35

Sophie: You, I know. Likewise.

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