Inside Figma’s early days: How to build a world-class sales org | Kyle Parrish (VP of Sales)

Brett: What do you think a founder should have figured out on their own before they're willing to start to bring in sales folks?

Kyle: I've always believed and I think in the last 12 months it has been really top of mind for a lot of founders and something that I'm seeing out in my network as well is the founder needs to prove, you know, product market fit, I think is a nebulous thing. It means different things to different people. What we've seen in 2023, and even part of 2022 is if it's software that's additive, the forward looking road map is really promising, but serving value today and something that people are saying, hey, this either solves a massive problem I have it helps consolidate a bunch of other products that may be using,

maybe it's in the new wave of AI, whatever it may be. If you don't have that conviction, and you're just building something really cool and, um, maybe the stickiness of the product or the usage that you're seeing under the hood is not there. It's going to be really hard to bring in a sales team because maybe you'll bring in a sales team and maybe they'll be great at conversion.

But the long tail of the business is just not going to be sustainable. And I think this is something that everyone's facing in this day and age. You want to be business critical software, not something that's nice to have. Nice to have has been thrown out in the last couple quarters.

Brett: Going back to what you were saying a second ago, how should someone figure out if they should go the IC salesperson first hire versus somebody who can build a small team underneath them?

Kyle: Yeah, I think the way that I've kind of had this conversation with founders, if you're a little bit earlier on in the journey, but you're kind of hitting that point where you are facing more opportunity costs, just in terms of how you spend your time as a founder. But maybe you don't feel like you have that conviction.

You're not quite business critical in terms of the problems you're solving the ROI that you're providing for these customers. It is somewhat a band aid solution, I think, and that doesn't mean to say negative, but to bring in a salesperson and have them take some of the load of calls and hopefully converting of customers.

It could be someone on more of the CS lens. I've seen it where a founder is successful early on, and they're not ready for sales leaders where they do a lot of the initial sales call and kind of conversion of customers. And then someone takes the, customer journey and the handoff process from there. Ultimately, the same founder that maybe doesn't have formal experience selling,

they don't have formal experience managing salespeople and leading and building sales teams. That's something that will get you maybe another 6 months, maybe another 12 months. But ultimately you're looking for that signal to say, hey, we've got an opportunity to add 3, 4 or 5 salespeople and we know that we can increase the business and the revenue run rate by X.

And when you have that conviction, then it's time start searching for a sales leader that can build that initial team and ultimately hopefully get you the next 18 months, 2 years. I think a lot of founders over complicate things trying to think. Think of someone that worked at a big name company, say Google, Salesforce, whatever it may be, and not really someone who has the right experience, whether it's working in the industry and kind of segment that they're going after, or if it's just working in early stage startups and proven that they've had long tenure in early stage companies, they had to be strategic and balance that with also being tactical.

You can't just live in the strategy as an early stage sales leader, but you also can't just live in the tactical because either one will lead to your demise.

Brett: Do you think the founder should have figured out some level of repeatability where even if they don't have an end to end baked sales process, they should have signs of repeatability that they can hand off to someone? Or do you think sales folks can come in and build the repeatability and the founder doesn't need to have done that before?

Kyle: I think that some level of repeatability needs to exist. And if you're doing sales, and you're doing that founder led motion, you've understood what are the questions that you're asking these customers that will ultimately expose some pain or opportunity. To then bring up the solution, your company, your product, how you solve that, why it's innovative and why they should care.

And really, why now, I mean, there's a lot of companies that can get people excited about their product, but it just maybe isn't a priority and it doesn't have to be today, but it has to be on the near term versus like, hey, this is cool. Come back to me when you have customers a little bit more traction and the products a little bit further down the maturity curve.

Getting to that threshold of certain number of customers. ARR, you should have an idea of what it looks like to do good discovery. What it looks like to convert those customers. And what you're really driving towards in that kind of pitch on the conversion and closing of deals and then how do you make them successful?

If you can't get them successful after the whole pre sales process, then it's all kind of for nothing. So, I think the founders should have some notes. They may not be perfect. I think what the sales leader or the sales person's job is from there is 

 to take what they've learned and go build on that, and hopefully they have experience doing that in the past and understand what the next phases of the journey might look like.

Brett: Can you share some advice on how to think about structuring that interview process? Let's assume the founder has done this work, they're starting to see repeatability, they feel like they can hand this off to someone. What do you think an interview process should look like for this person? 

Kyle: Yeah, it's a really great question. I think the first thing honestly is, are they really interested in what you're doing and what you're building? Do they care about the product? Do they care about the problem you're trying to solve? And that doesn't mean it has to be their passion and they sort of think about it on the weekends and every night.

But is it someone who's curious and put in the time. They have a meeting with the founder CEO in most cases, do they spend a couple hours before that meeting, before that formal interview, really getting to know your company, your product, what it is that you're looking to do, because if they can't do that, and they just come in and they say, Hey, I worked at this company or that company, or I helped scale this business, they're, they're not interested in what you're doing enough for me.

I think that's really, really important because these people really are more missionaries than mercenaries in terms of, building and scaling these go to market teams. I think the other thing is that you want to bring in someone who is going to be able to work with all types of, folks in the organization, you know, for me early on, coming in as the 1st head of sales at Figma, I met our co founder and at the time CTO, evan, you know and he

probably never interviewed a salesperson before, but I think it was really important and I learned all about, like, engineering's value system and what he cared about. And I think for the most part, he was testing is this someone who I think can work with my team, other engineers in the company, other engineering managers and leaders, because early on, you spend almost more of your time

with engineers, designers, product leaders as you do customers, because everything that you do is so iterative is so tight knit in this closed loop that if you can't work well with other parts of the business, and you've only worked at companies where sales is on the 5th floor engineering is on the 3rd floor, you're completely different campuses.

You're going to struggle to flourish in the startup world where there isn't a sales team. There isn't sales culture. You can't just hang out in in your organizations And I think I've seen a lot of, people that get excited and they've only worked in large companies coming to startups with that kind of mentality.

And they don't invest enough in those relationships. I think that's another thing that, you want to look out for as a founder as someone who can work well with the teams that exist today, and then start to evolve your culture. Culture is not stagnant and you don't want your culture to stay what it was from seed to series A to series B.

And when you bring in salespeople, you know that the culture is going to change, but is it going to change in a direction that everyone's excited about and encouraged by?

Brett: I assume the advice is, is it's not just, here's the 7 question playbook founder. Now you're off to the races. But let's say you were forced to sort of come up with something like, here's the 5 or 10 questions or

here's a little draft of the outline of the interview that I would recommend you consider doing. What are some of the things that would be in there?

Kyle: Yeah, I think one of the things that you can do is just almost have like a brainstorm. It's um, it's almost like bring them into your environment and let's just start jamming on ideas. What would you do next?

How would you think about it? Here's the customers that we're focused on. We're going after the SMB segment. We're going after enterprise. Here's the kind of contracts that we're able to convert today. Here's the feedback we get when customers don't convert and just get their real time reactions and have a discussion.

Of course, the founder has been thinking about this day and night building the product, building the team and so if you're not getting a good signal that a, this is someone that I can work with B they're intelligent and they can balance the strategic and the tactical and then c, they're actually you know, a really, really strong candidate.

You almost feel like you're getting feedback. This is a mentor. This is someone who can really guide strategy and someone who you want in your camp. Because if they were to come on board, it's a small group of people that's thinking about the go to market side of the house. And I don't think it has to be formal

here's these 5 or 10 questions. There are some good questions that you can ask. I think it's really like, you want to get to the meat of the interview and that, in my mind, is a discussion, a brainstorm where you can kind of get a sample size of what's it like to be in a room with this person solving problems?

Because so much of the job is problem solving again. Like I said earlier, but you have to be ruthless with your prioritization. You have minimal resources. And you can't do it all and you can't even do more than in my mind, you know, 3 to 5 things early on successfully. And so you have to limit the things that you do and be really vocal, communicating to that CEO and founder on what you are doing and why.

Brett: You mentioned a second ago, but if you were forced to give a couple questions, are there any that come to mind for you?

Kyle: Yeah, I think situational questions are probably really important. So tell me about a time where you worked with cross functional teams on solving, you know, maybe a challenge, whether it was like a bug or a deal, not closing. Talk to me about how you, think about hiring salespeople if you're hiring a sales leader.

So, what are you looking for in your 1st cohort of reps? If you were to get this job, talk to me about how you think about ultimately sales process and coming in as an early sales hire. What is the 1st thing that your mind goes to? What would you do in that 1st 30 to 60 days? An example of an answer that I'd want to hear is, like, if they come in and they're like, I'm just going to get in start closing deals.

I've got 5 AEs lined up I worked with at the last company. We're going to go hire those people. You're coming in and the 1st, 30 to 60 days is observing, talking to customers, talking to the people that are building this product that are marketing this product that are designing this product and really understanding how does this business tick what's working and starting to make, you know, some opinions on what's working? What's not? And then where am I going to spend my time and focus

so I think a lot of it really would be situational. You want to test out not just their experience, you can, anyone can do those boilerplate questions around past experience. The company I've worked for. I want to understand how they're thinking about coming into this environment with what they know this product, this customer, and see how they react.

Brett: Do you think founders should care about domain experience? 

Kyle: Sales motion experience is probably more relevant than domain experience. Domain experience is great. If you can get someone that has more of a sales motion that you're looking for in your current business, if you're building more of a product led growth business, someone who's seen product led growth businesses go from selling and building the early sales team and infrastructure to eventually every great PLG business has to have this top down sales motion. You want to see someone who's kind of been through that journey. If your motion is purely top down and in the market you're going after, you don't want to bring someone who knows 0 to 1 PLG per se, that may be less relevant to you.

I think domain expertise is kind of like tier 2. If you can find someone that has domain expertise, you know, whether it's worked for a competitor or works for an incumbent, that's always nice to have. I think it's more important to bring in someone that truly understands your motion.

 Are there things you've kind of figured out that are these kind of attributes of the top 1 percent of salespeople versus the top 10 or 20 or 50%?

Kyle: Yeah, I think that, you know, you mentioned a few, but I think 1 of the ones that I'm always looking for is resiliency. I think in this year, more than ever, especially for sales, it's been critical to see how people show up and show resiliency, but I'm finding ways in the interview to talk about past experiences. Some professional and some, you know, it ends up kind of talking about a personal story.

Not that I'm necessarily asking about that in the interview, but sometimes that's the way the conversation will go and you'll hear stories about where people hit a rough patch, how they got into the field that they're in, why they want this job, why they've been grinding to get to the place that they are today. Work ethic and resiliency, there's just no replacement for that.

And so I think you want people that have high IQ, you want people that have high EQ and you think they're going to come into this business and help evolve that sales culture in a really positive way. But at the end of the day, you want someone that you can trust is putting in the work and able to be there when the going gets tougher, because that's, predictable, you know, that there's going to be challenges along the road.

And I think the best hires that I've made and the best people that I've seen grow their careers exponentially from being IC salesperson to director of sales, VPs of sales, those are the folks that had all of those intangibles. But then when it came down to being resilient and being a team player and being collaborative, that's where they really shined.

Brett: And you normally get at that through having them share stories about how resilient they were in the past.

Kyle: It could be an example of like, so what happened here? You know, when, when COVID hit, there was a lot of stories where people got laid off. I think As someone who does a lot of hiring and a lot of interviewing, I value tenure, but I think more so than ever, and I'm always open to hearing the stories like what happened?

You left early, got cut short. I don't think anyone joins a job looking to work there for 12 months, 18 you know, they're hoping to be there for years, hoping to make an impact, grow their career. And when they leave, really use as a stepping stone to continue their career trajectory. But I heard a bunch of stories post-COVID of, like, hey, this happened, I got laid off or, we went remote and that didn't work for me.

I wanted to be in an office or whatever the story is. So I would really just probe and dig deep. And so I'd ask probing questions on, okay. So that happened. Tell me, you know, what was hard about that? How did you react? I'll also DO situation, uh, examples around deals or working and taking feedback. One of the things we've been on this journey of in the last few years.

Is just really understanding the importance of feedback in the sales organization. And making sure that people feel confident and empowered to speak up and share feedback and that's your feedback. That's upward feedback. If you're in a management position, that's downward feedback. And so having them walk through a scenario

where they got critical feedback and had to incorporate it. How do they handle that? And were they able to, you know, use that and get better and put it into their, their day to day kind of plan and how they go about doing their job? Or was it a setback? Because I think that what we find is a lot of people initially don't react great to feedback it's something you have to learn to kind of handle and expect.

Brett: Do you think being resilient is something that tends to be deeply built into somebody, maybe kind of related to how they grew up? Or do you think resilience is kind of like that muscle that can be exercised and grown over time?

Kyle: I think certain people are forced to be resilient earlier on in their lives, depending on their circumstances. That's for sure. But I do think that it's something that you can build on. And if it's something that, you know, maybe you haven't had to show as much resiliency in your life. I think that it is like a muscle that you can build and develop.

And the reality is that, you know, whatever it is, When you're interviewing someone, you don't know their life story. You don't know the career story. You have a lot of empathy for where they're at today, meeting them the journey that they've been on. We all know that life isn't easy and everyone has some level of resiliency.

For me it's about understanding how they've taken these moments, these setbacks, these journeys, these opportunities it can even be positive things and how they've internalized that and built it into how to think about you know, in this case, going to work every day and seeing the kind of light at the end of the tunnel.

Sometimes it's easy to get caught in kind of what I call chicken little syndrome, where there's stuff happening in the macro environment. There's something happening internally and it's really easy to get spun out of control and think everything's screwed. Nothing's working. Everything is doomed and those are the kind of people that generally, you know, get labeled as toxic and start telling everyone else, like, this place isn't a great environment.

We can't be successful here. We can't be successful here. And I think that you want people sharing feedback around where you can improve as a leadership team as a business. But resiliency is when you're sharing feedback, but also believing in, like, the mission and the longer term strategy and execution plan.

All those little ups and downs along the way smooth out over time, you know, I see a lot of people that make hasty decisions. And then I think that, leads to leaving a company too early under performance, getting managed out of the business, whatever it may be. And so it is a hard thing to test for, but I think you develop a gut and an instinct for it.

And you find ways to kind of suss that out of people in interviews.

Brett: You joined Figma in the early days, you were the first salesperson, sales leader. And I'd be really interested to hear about what the first few months looked like.

And would love you to sort of share in as much detail, even if it feels mundane or boring, in terms of, what are the things that you did when you showed up for the first day?

Kyle: When I joined the company, it just raised our series B a few months earlier. I think there was about 40 to 45 employees, give or take. No sales team. We had this product that was in a beta. So, when I joined, the 1st thing I wanted to do was meet customers get closer to the product and understand, like, how people were using it.

There wasn't any really formal documentation notes. So Dylan and Claire, who was on your show in the past and a few other folks have been talking to customers and working with customers and converting customers over the years. So, even though they didn't have a sales team founder led sales community led sales was kind of happening in some ways, but there was no documentation.

I couldn't come in and read the notes on working with Microsoft and what that relationship looked like, so that was a challenge and very limited information on what was happening in the field. And the other thing that Dylan asked me actually to do in the 1st, month of joining, was to join the support team.

He asked me to not do anything on the sales side, spend 4 months with the support team in the support queue, working on bugs, understanding the ins and outs of the product. And at first I was a little taken aback. I was just hired to help this team build their business, drive revenue, hire a sales team and now I'm going to go hang out with the support team and work in support queue.

But it was a test of patience I think in a lot of ways, and it ended up being this amazing turn of events. I spent time with our support team, which is awesome and still a huge part of Figmas success and business today. I got on all these ins and outs of the product. I got to learn the product at a level that I probably never would have.

if I didn't spend that time there, and I think most importantly, I got the opportunity to develop a relationship with the support team and show them that I really wanted to understand how this company operated, what our customers cared about, that allowed me to have this kind of strong relationship out of the gates that we're going to build a different sales team here at Figma

and so when I got to back to the job, if you will, after that 4 weeks, then I had a lot of information and context, I just couldn't get anywhere else. It ended up being 1 of the best starting points.

You know, sometimes you have to take 2 steps back and ultimately I think moved us 4 steps forward in that 1st, 90 days.

Brett: When you were trying to build context and talking to Dylan and Claire and others, do you remember the types of things that you were asking? It seems like there's an unending amount of context. I mean, they had been working on the product for years at that point. They had early customers.

What was the type of information you were trying to get from them?

Kyle: It's a great question. And it's pretty daunting. I mean, for those that maybe don't know Figma super well. You can do a 5 minute overview demo of Figma or an hour and a half demo of Figma. I mean, there's so much depth to the product and that was before we had FigJam or whiteboarding product or or dev mode or product for developers.

But at the time, you know, there was a lot of depth to it and so I think it was daunting in the sense of I spent time with support, I was trying to learn the product as best I could, balancing again with other things that I had to do, to get the sales team kind of off the ground. But early on, I was trying to understand, hey, why did you use Figma? I mean when I joined, there's still this fear of, like, hey, it's creepy to jump into a file and see Brett, my manager, or Brett, the developer that I work with when I'm not ready to share my design work, that kind of concept was scarier than it was again, in terms of workflows. And so Sketch was the kind of dominant design. Tool of that era and InVision was, was like a fast growing, kind of dominant business for sharing prototypes and had a little bit more of a collaborative arc. Early on

I was just understanding like, hey, why did you even give Figma shop? Why did you give them the time of day? And then once customers have been on the platform for a while, I was understanding the value they were getting for from it. And I was understanding all the different personas that were using it. Early on, even myself included.

I can't say that I saw the full picture of all of the different people that spend time in our platform. And in that 1st, few months, then I started realizing that, you know, more than half of our user base on any given customer account was not the designer, so you have all these different folks from, product managers to developers to, UX writers to all of these people that are collaborating as part of the digital product development process. And so, for me, that was just eye opening. I was just trying to learn how are you using this product? Why? And then, of course, there was a commercial side to it, too, for the customers that were on the enterprise beta.

I was trying to understand, was that differentiation strong enough? You know, we were working through what is the price point that we're going to ultimately charge these customers and trying to make sure that that felt like something that was palatable, but also was was pretty bold in what we launched.

But yeah, it was just really, I felt like a researcher in a lot of ways that we were just asking a lot of questions, developing relationships. And I think 1 of the saving graces was just how warm the design community was. And that was a huge testament to the community that already existed. And I think Figma's go to market approach early on, even before my time in being able to understand those people connect with them and then doing discovery

calls with the folks, it's like, you better bring a notepad because as opposed to selling IT which was a lot of my experience Dropbox I would just get paragraphs of notes. So much detail, but early on, you want that verse the opposite where you're trying to talk to a customer and they're very tight lipped about sharing anything about how they use the product or why they would use a product or or why they would care at all.

Brett: Can you say a little bit more about what those first few months looked like? The direction you could go was so broad. You could go do IC deals. If you did that, you could focus on mid market accounts or up market accounts or growing accounts organically.

You could go start to build quote, you know, sales process, and so interested to learn about that pivot to actual execution. 

Kyle: It was probably around the 2 to 3 month mark. Like I said, we hired a couple of AEs that they'd already been interviewing before I joined. And so it was the 3 of us for the 1st, 6 months. So I had 2 AEs working with customers along with myself and we were kind of fast moving on all those fronts.

1 of the things we had to do was literally build an order form. We had all these customers that started using the beta. We were going out and taking more customers and trying to convert them onto a beta. At 1 point, we had this engineering script that required, basically this 1 customer at a time. I think it took around 30 minutes to convert from our pro tier to our organization tier, which is our kind of business enterprise tier at the time and we started successfully as a sales team, getting a bunch of pipeline built up, but we have this massive bottleneck bandwidth constriction and I think 1 of the things I had to do as a sales leader was understand what

the engineering team was dealing with, what were the parameters that they had to work through? Because I was like, hopefully you can see where I'm coming from. Like, this, can't be a blocker to converting customers to beta that ultimately become paid customers. So, that's 1 of the things that we did, I think the other thing was, we started setting up the sales force process and infrastructure.

I had a great partner in crime in a Praveer who's our CFO now at Figma. And we did a lot of the things that I wished we had a Dropbox. So, this is where, again, for me, and I think, you know, big part of probably Dylan bringing me in was, hoping that experience would be relevant. Dropbox is 1 of the, you know, kind of OG companies around PLG building this top down sales motion.

And so we got to build things from the ground up with our Salesforce instance, using a reverse ETL and all of these products that were kind of merging in that time, 2018, 2019, so that we could actually pipe product data into Salesforce. So, as we started building the buzz, getting more leads, our focus is on conversion.

We were able to able to actually prioritize who we're spending time with based on usage you know, number of design editors in the platform. We were also able to layer on the Clearbit data and look at external data and enrich it. So, we can see if it was a larger company and their internal usage stats were strong

that's where I'm going to spend my time with that's who I'm going to direct those 1st, couple of salespeople to go jump on a call with 1st and we're going to get to everybody. But again, the name of the game is prioritization. So, a lot of it was balancing in the field, talking directly to customers, understanding where they were at and trying to convert them to get onto this beta.

It was going to go live back in January, I joined in July and January, we're going to, come out of beta and start charging these customers building the process and infrastructure. So then when 2019 came, we launched the product. We could hire salespeople. We could scale this kind of playbook and go to market strategy and plan

we had to many more reps and segments, et cetera. And I think the last part of it was, the, you know, less sexy stuff, building order forms and working with our counterparts in the finance team. Like, there's no infrastructure built when you're that small and you just haven't really gone into a commercial model that requires customers signing documents and then legal reviews.

We didn't have internal counsel so customers want to do red lines. We're working with external law firms. I think 3 or 4 of them at the time. So you just don't have a lot of these built out swim lanes that you do once the business matures and so you have to be scrappy 

and pull it all together, so, 

some of the best days of my career but you know, there's a head on a swivel 6 months. Uh, I did not know what that day was gonna bring like, I tried to plan and come with with ideas and what we're going to do, but everything was so dynamic and changing that we just kind of had to, you know, prioritize day to day on what we're going to do and what we're going to get done. 

Brett: Were most of those early months in terms of execution really oriented around existing pilot or beta customers, getting them to convert to sort of normal ARR generating customers?

Kyle: It was a blend of 2 things. So, in a freemium kind of PLG model, we have people that are signing up for the free product of Figma. And then we also had people that were paying via credit card for our pro plan. So, that was a self serve business that can go on to Figma. You hit a paywall, you jump into pro.

And so it was usually someone who'd been just started out and free. Sometimes we would get engaged with people earlier or they were using pro. I think the other thing that we had was kind of the beauty of the PLG model. And I think the timing of bringing on myself and starting to scale the sales team was that we had a lot of hand raisers, people that were going to contact sales

filling out their form and saying hey, I'd love to hear about the business tier of that product. We want to understand how we can use this and maybe it's more of a secure manner. What are the other features and functionality that you guys are building for businesses that we're bumping up against? and then we would, you know, have the conversations with them focused on at the time

it was this I think the beauty is that we were able to focus the sales motion and all the early enablement efforts on taking people from anywhere from 3 to 6 products into 1, all in 1 design platform collaboration built in. And if we got them to do that, and they're already doing a little bit in pro, we were able to convert them to enterprise.

Because I think that the team did a good job early on in pressing and packaging building features and functionality that people care. And I think there's generally 3 pillars can you impact the end users and converting to enterprise security. Um, Um, you know, that's a very large bucket and I think the admin experience, whether it's managing users or managing content.

And we had thoughtful, kind of features and functionality across all of those 3 pillars. And so the execution was signing basically 0 deal contracts that would go live in January, and then that revenue would start converting.

Brett: Did you think a lot about either sector or company size, or it was all over the map? Meaning did you spend as much time thinking about and caring about Microsoft being a potential early customer as it was kind of a 250 person venture backed tech startup. I often sort of see companies being quite focused on, on sort of somewhat narrow of an ICP or a persona and then they expand over time.

Did you focus in that way or was it kind of inbound oriented and if there was an interesting company who was excited about the product you would go spend time there?

Kyle: It was inbound oriented and I think. The answer is that we tried to focus on both, no doubt our largest customers and we were fortunate to have some early in the early beta, uh, you know, Google and Microsoft and square Uber, Airbnb, you know, they were very vocal about 

Figma 

I think early on in, within the, the niche design community, they of course were, were very close to our engineering product and design teams, like we were building the product, getting their feedback,

whether it was via support channels, via direct relationships, via the sales team. We were talking to those customers almost daily. But one thing that I wanted to make sure that we didn't do was neglect smaller customers or customers that weren't as, engaged or as far down the process in migrating to Figma.

And so what we did when we went live in January and really started to scale hiring was just simply drew the line at 1000 employees. 1000 employees and below was SMB mid market. 1000 employees and greater was enterprise. it was easy to do because that's how Clearbit also cut the data. It wasn't necessarily scientific.

But I think that it allowed us to hire folks that were focused on just a different segment of customers. I think that's really, really important. The other thing is to your point for some companies, maybe it makes more sense to just be maniacally focused on serving SMBs because, you know, your product falls down if it goes up to larger enterprises.

That I think is 1 of the unique things about Figma was that we were solving problems around distributing your design system and really unlocking collaboration in the design and digital product development process that also serve to Microsoft. There was things that Microsoft wanted in the security bucket and the admin bucket, you know, and a bunch of things that we, that we had to go build.

We solved enough of a problem for them that you had 1 of the biggest companies in the world building their digital products on Figma and it wasn't their entire team on day 1 of course, we were knocking down large swaths of the Microsoft team. and so, for me, yeah, it was making sure that we had the right people and we were balancing both of those notions because I didn't want to give up, you know, the opportunity.

Brett: How did the messaging evolve those, I don't know, first two or four or six months, if it did in any way?

Kyle: We kind of fell into and, um, you know, I'll take full responsibility in the sales team. what designers have always talked about the tool, the design tool, you know, it's a little bit of a pet peeve for me now, but I think we'd always talk about Figma as a design tool. And like, I told you, the deeper we got into it, and the more

you know, we're just understanding the pains and challenges that customers have how broken collaboration was and working with all these different parties that aren't just designers. And I think outside looking in, they're like, oh, there's that design tool, you know, that's a pretty small Tam, like, that's not going to be that big of a company.

And then when you start working in my job, and you see how customers using the product, all the different types of people in product, how engaged they are, how much it's speeding up the ability to build your products faster and ultimately, you know, drive the business forward. That's when it got really powerful.

And so we shifted probably that, like, 6 to 12 months mark from calling it a design tool to calling it a design platform. And it may sound small, but that really got customers thinking. I think that's what you'd see at that time, from a marketing standpoint, from a scaled outreach, we call them, live demos, not webinars because webinars is not seen as cool in the design community.

But we really started making this intentional pivot to being a platform and that's really what we are, what we were and what customers are seeing us as because they were going from a bunch of different tools that did small parts of the process to 1 all in 1 platform that lives in the browser that's collaborative.

I think that was a big breakthrough because I think we're really pidgeon-holing ourselves and just not, doing enough storytelling and like, leaning into that narrative with customers.

Brett: For most of the, 12 or 24, 36 months after you joined, for most of that time, was everything just inbound oriented? Just engaging with customers who are already in the product, converting them over? Was there some outbound or more traditional enterprise orientation or sort of, what did that look like?

Kyle: You know, we were fortunate to have probably 18 months to 2 years of healthy inbound business. And even that we had plenty of inbound and opportunity just as the platform and and user base grew. But at some point, I think you want your sale leader pushing that fine line of okay. Great.

You've proved that you can convert in on interest, because that's kind of P0. You want to come in and make sure that customers are excited. You're jumping on calls with them. You're working with them directly and they're converting to your business or enterprise tiers. Once we staffed up the team, and you start giving people territories, and we were segmenting, and we brought in managers and frontline leaders, you have people that have territories,

and we were basically saying, okay, we're going to round Robin leads and that's 1 part of the business, but we're also going to give AE's books of business based on usage, so all this stuff we did early on working with census, which is a reverse detail company and that's stuff that Praveer and I, and a handful of other people kind of built early 

on.

It really, you know, it's still live today, but the 1st, 3 years, that was our big bet, and it ended up paying off because we were focusing on the companies where we were seeing we could actually put in who's most active in the Figma platform, and it would put in an email. Kyle at Figma. Who's shared Figma the most, which means that they're kind of part of that flywheel and driving the collaboration.

Then we would see all of 

the 

analytics across the domain. How many files, how many components, which is an element of a design system. All of these were triggering this kind of homegrown account based model that we built and then we go put that in reps territories. So, the 1st iteration of going outbound wasn't just knocking on cold doors.

We had this whole usage model. People weren't coming to us maybe. But they were using free or Pro Figma in some way, and we were trying to get to them as soon as we possibly could so that we can guide that experience and show them that you know, those are great products and it's kind of how you get started.

And for small groups of people, that's awesome. But if you really want to scale this to your entire business, to your entire design team to multiple design teams, you know, you should be working with us on the business tier.

Brett: What was pricing and packaging like in the early days? I think this is a question that everyone struggles with and debates all the time, what did you sort of land on and how much was it this just directionally seems correct versus a little bit more sort of science behind it?

Kyle: Yeah, so for, Figma pro, it was 15 dollars a month, if you wanted to pay monthly. You can do it annual and that was 12 dollars a month for the year. And then our enterprise tier was 540 dollars for a design editor. It felt at the time where it was, it was aggressive in a good way, but customers were not balking at the price either.

And it was almost a 3x jump. You know, it wasn't 3x jump basically going from if you were like a monthly customer to our organization tier. I think some of the unique things about Figma that help this drive that is going into the space that we were working in some of the incumbents charged for viewer seats as well.

So, for Figma, if I'm editing, I'm building something in the Figma canvas. I'm sharing it with Brett. Brett comes in, he's commenting, he's viewing the files, but you're not making any edit actions. You're actually a free user. And so we were able to go into companies that were, using sketch using InVision, maybe paying for both of those products for all of their user base and say, yes, this is the price that we landed on with conviction and talk about the kind of ROI behind Figma.

But also, you've got maybe 60%, 50%, 40 percent of your user base that will be free non paid users. So, when we actually package together proposals for customers, we wouldn't just say you're going to pay for 100 licenses. That's going to cost you $54,000 for the year. We would actually talk about the total value of the contract based on how many people they either anticipated to have in the platform already had in the platform.

If they were on a trial, or had been using it previously. The other wrinkle, I'll say with Figma that was interesting. This is the 1st in my career was that early on, Dylan said, we don't discount. We're not discounting the product. You know, it was the right call and I think it was something that made it really simple.

Once we got the team scaled up in terms of negotiating, but there was a lot of friction, you know, early on, specifically for me and, you know, even 1 point had to bring in Dylan to let one of our largest customers know that, you know, this isn't just coming from the head of sales, the VP of sales, the CRO, we don't discount our products and, um, we're fair and consistent with every customer around them that pricing strategy.

Brett: How did you end up on that idea of maybe charging more for the active users who are editing and creating and then not charging at all for the consumer users, sort of bifurcating the pricing.

Kyle: Yeah, and that actually predated my time, but I think just hearing about a lot of those conversations early on, we know that the value provided to a designer is immense. We're asking these designers early on and every day that they stay in Figma thereafter to spend 8 hours, 10 hours, 12 hours in the product almost every day that they're working.

This is something that you know, is there a core tool, I mean, it's their home base. They're coming in building, collaborating, sharing their work, all of it. And I think the value that we provide those editing and Figma is events and felt justified for the price point that we landed on and charging for. I think 1 of the things that we wanted to do was just unlock collaboration.

And so Figma was really good at building this collaboration model that felt seamless. I mean, people get in there, like, it's so easy. I just sent you a link. I either hit the share button, copy pasted the URL, dropped it in slack, dropped it in our zoom call. All of a sudden you're in the file. You're seeing work previously

that was completely blocked off. You do work in sketch or designer. Let me move it over to a slides tool and then jump on a call with you and I'll walk you through it. Let me email you a static PDF of the work I've been doing. It was not real time and collaborative. And so I think 1 thing that we wanted to do was just make it so that price point wasn't sticking point for anyone coming in.

That maybe wasn't like, I'm going to be spending 8 hours a day in this tool or 4 hours a day, whatever it is. And I think that was, you know, 1 of the best decisions they made early on was opening up this value. And like I said, it's 1 of the most critical things I learned in those 1st 90 days. I came in and I was like, wow.

This is so much more than just designers building products. It's all of these people collaborating, communicating. I'll never forget. I was working with Twitter. They were 1 of our 1st, 20, 25 customers and 1 of the design leaders I went and met with them at the old Twitter HQ, and he was just kind of walking me through the previous way of working and then now working in Figma and how like

all of the people that they have to work with are now in the product can see what's going on working around the same kind of contextual work, uh, not having to share side notes about what's happening. Why does that exist? They were seeing the actual work being done and how it would not drop off of a cliff.

They were a global business at that moment. And he would talk about when he logged off, you know, someone in APAC would come online and they'd just be totally lost. Where do I go from here? Brett made some changes to the file, but it's not documented anywhere being this browser based tool. We had version history that people can go in and see.

And so I think that we got more people in the product, which just made it more powerful and, kind of added to the overall ROI that we bring businesses.

Brett: Did you end up over time adding different types of users at different price points?

Kyle: We never did, so it's still editors and viewers, but we did launch a whiteboarding product and that same kind of model carries over to that. And then most recently, we just announced our big conference this past summer dev mode, which is a product. Uh, specifically focused for developers, so a lot of that was built off of feedback and just opportunity that we saw over the years.

We already had a ton of developers in the product, but a lot of the experience that we built in the Figma design platform was not specific to the developer experience. And so I think that's a big opportunity for us and something that we're really excited to go from beta to release, in January of next year.

Brett: I'm super curious to hear more about what did you end up figuring out 

existed 

in terms of differences between your experience at Dropbox and your experience at Figma?

And I would assume that you spent a meaningful percentage of your career prior to Figma at Dropbox. And particularly at the time that you were there, those were sort of the biggest years of the company. And I would assume it would have been easy to say, listen, I've been there, done that at Dropbox, an enormous revenue base, I'm going to kind of go and redo that.

And I'm curious, what did you find out ended up being very similar in terms of this topic of sales and PLG? And what are the things that you found, you had to kind of go back to first principles or unlearn or, or start over on?

Kyle: The 1st thing I'd say is that, you know, Dropbox was a life changing experience for me as my 1st tech company with my 1st startup. I mean, I always say I grew up at Dropbox and so I learned so much. The network of Dropbox and I think you know many of the folks from the Dropbox network that I know, I mean, it's just everyone's spread out doing incredible 

things and it's continuing to pay dividends. You know, knowing these people, having an opportunity to then work with them and seeing them shine in, in the companies they're, leading as founders, as as leaders, as ics, whatever it may be.

But I think some of the things that Dropbox didn't do well was a big learning. I think it was a big learning for companies like Slack and they've even said publicly, like they, a lot of blueprint of kind of the PLG motion, but hunkering down and being like, we are a B2B company. Dropbox always had a bit of an identity crisis.

We were this consumer company that was just, you know, printing money and a large portion of the revenue base came from that. And then we built this really great B2B business that got into the hundreds of millions of ARR. I don't know where it's at today. But there was constantly this struggle that people were building features, functionalities, and really like experiences and solving problems

for the consumers and trying to get people that were excited about doing that for the businesses. You know, we're B2B, we're enterprise and I think we waffled on that for too long.

And then, you know, long after I left, they kind of double down on enterprise and that was the move, but they miss a bunch of different areas that could have been interesting to launch new products to grow market and continue to increase the market cap of the company, which has kind of held sturdy since the IPO 5, 6 years ago at this point or 7 years, Figma.

Is not. B2C in any way, I like to say it's almost B2IC in a lot of ways, everything that Claire and Dylan and all of those folks that were involved in building the community nailed was really understanding what makes designers tick. What do they care about? And if we're going to go build a product that makes their lives better, ultimately is the future of working.

What does that look like? And so we have this B2IC motion, but anyone that's using Figma, whether you're an individual designer and building a consultancy shop, you work at an SMB, you work in an agency, or you work in Microsoft, Google, or any of these large companies, you're using it in a business capacity and that kind of culture around

we are solving problems for people that are using this in the workplace for a professional role came from Dylan and Evan, our founders all the way down. And so there was never this identity crisis. So when we started going and building the product feedback loop at Dropbox, it existed, I learned how to operate really well with engineering and product design teams, but they were never going to go build what sales was asking a Dropbox.

You can ask anyone that worked there in my time, they would, you know, be very cordial, very friendly. We'd have good debate, but they weren't going to go build those things in the product. It wasn't going to be on the roadmap. And we missed a lot of opportunity. At Figma, I've never seen a tighter, especially in those early days, product feedback kind of loop and relationship.

And so when we were giving feedback, we were all completely aligned around what we're doing as a company, what we're doing as a business and how to go forward. So I think that was a big part of it. The other things I learned, I mentioned, you know, like, we learned way later we wanted to use usage that we were seeing in the product, have it at the fingertips of the sales reps.

I want it to be in Salesforce. If that's our rule of record, I want it so they don't have to go into some kind of internal tools, which is what we did at Dropbox. Which was great and very innovative at the time, but it was basically this internal admin tool and I had to type in a domain and, you know, query for anywhere from 3 to 20 minutes.

It wasn't, snappy ready to go. What we've built at Figma. It's those tables are being updated every 30 minutes. I can go look at an account right now and see how many active users? How many licenses are they paying for? What tier are they on? All of this stuff that is just so powerful, especially for people that have multi tiers of their products and are looking to convert people from, you know, no Figma or free, pro, et cetera.

The last thing I will say is that in a PLG business, like a Dropbox, like a Figma, you always want to lead, whether it's doing sales outreach, whether it's working with marketing on events, or just the overall marketing narrative, you want to lead with the value you provide the business case invited by bringing in your products, not in a fear tactic way.

And I think Dropbox didn't know better at the time, and we kind of iterated and realized what didn't work, but we had this kind of motion that was like, hey right, you're the CIO of NBC universal let's say. Did, you know, all these people are using your product and I think informing that person's not a bad thing, but sometimes, depending on the sales rep, you know, it felt like it was teetering a little bit more on the, poke the beehive and that didn't always go well.

Some people would look to just drop block Dropbox out of the gates and they didn't want to kick off a conversation in that way. So, what I learned at Figma is like, hey, we do reach out to people that are using the product. We do know that you're using the product. Of course, we work on the sales team and we're going to kind of connect with you and drive that relationship, but we're going to do it around the value of what we provide and why you should take a conversation with us. And what else we have to offer, not, hey, you're not using a secure version of Figma. Talk to me and let's get you upgraded.

Brett: How did you approach creating the right dynamic and culture between the early sales org and everyone else in the company? There's always this challenge. I think it was probably particularly accentuated with Figma because the company had been building for so many years, where you have design product and engineering centric company and you have your first sellers join there's either this dominant hand problem where if you're, you know, engineering oriented, you tend to be continue to be engineering oriented.

Or there's just a, I don't like sales. I want to focus on talking to customers and building features. What did you do to sort of, um, build bridges and kind of create that level of cohesion that led to what you were talking about, where there was this tight coupling between sales and what you were hearing from customers and then asking engineering?

Kyle: You know, my worst fears were that the suits are coming in we're going to build a team team where we're going to be allergic to the culture that they had there and everyone was kind of going to be, I don't know anti sales team, because it was known, you know, Figma had this cool and very dynamic and connected culture at the time.

And my advice to anyone taking on jobs like this, being that early go to market leader or sales leader is, you know, don't come with preconceived notions because they couldn't have been farther from the truth. I came in and people were eager and curious. I have a friend who was like, oh, great a sales team.

Like, you know, I want to keep growing. I use it as a product manager. I want to keep building this business. I want more people using products. Not oh, I've heard these horrible stereotypes about tech salespeople and now this company is going to start changing in a way that maybe is not something I want to be a part of.

And I think credit to Dylan. He did a really good job at our all hands meetings, not just talking about company updates or, you know, a story from an engineering team or product or recruiting. He paved the way to tell stories, we would call it sales tales early on, and we would come and not just talk about wins and deals and revenue.

I was, of course, part of it, but we talked about interactions or, contested, you know, customer conversations you come in and they're kind of out for, hey, this is not the way of working. This is not the future. We're not going to be converting to Figma and being able to convert those people working with the team that we had designer advocates, which is part of our community arm as well.

And they're basically sales engineers, but former designers, and so they're able to come in alongside the sales person, give credibility. And so that relationship ended up being 1 of the strongest, and they're a huge testament to all of our success. Because we kind of created the role that didn't exist before.

And so now we have someone who can come in who has seen the landscape of design design tooling change over 5, 10, 15 year period and they're able to convey confidence to customers because, like, I told you earlier, like, Figma's a very deep, very technical product. And so our salespeople also we're very curious and dug into the technical aspects. To today

everyone has to do a demo of Figma as part of the interview process. And if you were the 1st, 25 reps, you have to do it with myself, Dylan and Amanda Kleha, who was our chief customer officer. And that is a pretty intense experience: doing a really technical demo with the founder of the company, but it came down to, we would get people this prompt.

We would say. You know, here's the allotted time. I think it was always a little bit underestimated, we say it's 4 to 6 hours, probably close to 8 to 10, and it was a great way to weed people out. But then when they came on, there was almost this kind of built in. relationship and energy with the people in the house that we're building the product or marketing or, or, or recruiting and HR, because they had to kind of climb this mountain and get onto the team and show that they were curious they were committed and they would put in the work.

And so 1 thing for me is, once we got people in, it was just making sure that we were bringing on the right profile people and kind of building the anti tech sales bro culture of Figma. I think A 1 that I felt was diverse and going to be the most successful team, but also B, it was going to resonate most with their customer base and the people that we were selling to. The same maybe brash challenger sales methodology sales rep that works at, you know, some other companies

it's just not going to work at Figma. and I'm really proud that even today, 6 years from starting this job and starting the team. Whenever we get the team together, the culture is still there. It's still strong as ever. And I think when you get your customers leading and saying how great the sales team is, like, those are like the highest praise that you can get in my position.

And obviously the revenue growth and the business success comes as a byproduct of that. But when people actually. Take the time to call out on social media, how great it was to work with your team. Like, that's what it's all about.

Brett: You mentioned this a second ago, but I'm interested in where there are other rituals in the early days that you all did that were kind of interesting or unique? You talked about sales tales you just talked about in the interview process, each potential rep had to demo the product for you and Dylan and others.

Are there other sort of unique little rituals or part of the operating rhythm of the sales team that might be interesting to explore?

Kyle: Yeah, I think 1 thing we thought about was that, hey, we're trying to sell to an audience and we have some of the best people in this profession at the company. And in the early days, we were all in San Francisco, you know, covid had not happened. We were very much an office culture. And so we would actually go to the design crits design critiques where designers and product managers would come in and they would tear down things that people were building and shipping.

And it was so interesting because we got to see all of the level of detail that they were tearing down these products. And you start to open up your mind. You know, I mean, I think of myself as a little bit creative, not a lot of bit creative. But when you spend time with creative and you see what they see, it's like a whole different world.

And so I think that curiosity and spending time with people where they were like, yeah, totally bring your sales team in. So it'd be myself 6 other reps and we'd come in and they'd even like, let us ask questions. We don't want to derail the meeting, but a design crit is a huge part of the development process and the design team getting together and kind of sharing ideas, critiquing them.

Of course, turning them down, building them back up. And coming out more aligned on all right, what we're going to go do and what we're not going to go do and not going to go spend time on. And so it was really cool to have some of these iconic designers. Rasmus who, you know, I actually had an opportunity to work with the Dropbox and he was the 1st employee at Spotify and these people were famous and prolific and we got to spend time with them.

And so then when you go to a customer call, you have way more confidence understanding the environment. You can ask good discovery questions are rooted in kind of understanding what their job looks like, what their day to day looks like. So that was really powerful. And I think that, you know, not every engineering product or design team

would let their sales team come in and maybe think that we're going to bog them down or just be a nuisance, but they couldn't have been more open and inviting. Little examples like that, I think is what made, Figma's go to market and just kind of team so, so unique and successful.

Brett: Anything interesting that you might be able to ,share about the first 10 or 20 hires on the sales team and how you thought about the profiles and org structure? You mentioned when you joined, behind you a couple months later, there were a few IC reps that joined. But you didn't kind of complete the story in terms of the next 12 or 18 months, how you chose to build out the team.

Kyle: We did some early segmentation. Um, basically 3 things. We divided the team on the AE side by mid market and enterprise at 1000 employees. And then maybe 6 months later, after that, once we, we started bringing on customers at a pretty 

fast clip and were growing quarter over quarter. We actually hired someone just to be on the sales team, knowing they had past account management experience. And I was kind of already thinking of the future and wanted her to be the 1st account manager and kind of pilot that. When we looked at, we had all types of different profiles and backgrounds. Again, I think, you know, the early team, both on the leadership side and just brought our sales where it was probably.

60%, you know, female, we had people from large companies, Twitter and Square. We had companies, people from startups who'd kind of been in a couple of startups, but maybe spent some time in a larger company. We had someone that came early on from InVision, you know, getting that domain expertise. Not a must have, but it was a nice to have, I think, as we were building out the team, in the early days.

And I think for us, it was that focus on on the net new side of the acquisition side. We're segmenting around the smaller customer, which is very engaged and curious and technical. And then, like, this larger scale 1, where we're trying to get do deals and expand them even before they end up joining and in that contractual phase, very much a land and expand business.

And so we wanted to always throttle that line of, we don't want to slow down the sales process to get the customer to their max spend and account value. We want them to get on the product because when they get on the product, we are looking at, you know, average sales price and try and increase that. We know that we're going to be able to truly unlock that collaboration experience and then ultimately expand the account.

And that's really what worked for us. So we had people from all types of backgrounds that joined the team. And I think that those 1st 20 people had someone who worked in tech sales for a couple of years out of New York at a media company was a Broadway performer. We had someone that was working, in the, uh, semiconductor industry.

Super sharp, interesting background and never sold sass and never sold was kind of on the business development partnership side. We had someone who was a. Um, she was an, uh, Olympian and had sold only like large scale companies working at Twitter and some of these bigger businesses. So she'd never worked in a startup.

I remember we're walking to Salesforce Park. She was our 1st hire. She's now a director of sales, lives in London, then used to do great things for the company, but she, uh, had never worked at a small startup. And I remember my job as a manager was to convince her don't worry day by day, we'll figure it out.

We'll get an order form. We'll have a sales process. We'll build a commission plan. You know, she just had only work to companies where all this stuff was figured out. And so you really needed to get people that were bought into the mission, super passionate about what we were doing as a company business, but also people that, I felt I could trust and that they could trust me because you're really getting them to buy in that, like, this is going to look like a real company.

Cause right now it's kind of a group of people just rallying around, listening to calls, talking to calls, joining design crits. It was much more art than science in those early days, and you kind of have to be comfortable with that a little bit. 

Brett: What did the the sales interview process look like for those 20 hires?

Kyle: so you would interview with Dylan, you'd interview with Amanda Kleha our chief customer officer myself, you'd interview with a peer on the sales team and if all that went well, then you would basically, uh, and I believe you interview with someone on the marketing team as well. Then you would come back, so that was kind of phase 1.

If you made past round 1, we would give you that exercise and give you the homework and say, come back we want you to demo 

Figma 

and create a mobile app. There's a bunch of tools at that point that you could kind of learn to create it. So we actually give you a link that should be able to make you a mobile app, but we wanted you to do it and then show the features.

And we're very 

kinda 

open about it, you know, you could talk about prototyping about anything and it was crazy some of the directions that people took. But I think of those 20 people, they all spent at least 10 plus hours learning the product. You saw creativity. You saw curiosity. You saw the light bulb go.

I would talk about these early sales hires. You don't have to ever want to be a designer and you don't have to ever want to to be working on that side of the business. But if you didn't get excited watching YouTube videos, toying around with Figma and seeing the potential and understanding kind of what the status quo is versus where we're going as a company,

then this probably is not going to be the job for you. And all of those people that super excited. They're like, wow, I had really had fun with this and I'm not sure if we've ever used to Figma but you get in, you're in a prototype and you can kind of see this is cool. It's dynamic. If you've used any Google docs or collaboration tool of our era, it felt pretty native.

There was a lot that wasn't native, especially for salespeople, but a lot of the collaboration and jumping in and problem solving was there. And so, it weeded out a lot of candidates that just didn't put in the time showed up poorly, Just didn't care enough wasn't weren't interested enough and we did that for 3 and a half years.

Eventually we got Dylan off of that. We still do that as part of the interview process, but Dylan interviewed every candidate and saw their presentation for about 2 and a half years.

Brett: Do you remember the best one of those first few years? Like, what did the person do in that demo?

Kyle: I saw a lot of really good ones. I think 1 of my favorites was actually someone who's on the team today. The 1st, 1 was not great. And this is a big part of resiliency. So I'm like, there's something here. I think this woman's going to be great. I think she's going to make a big impact at Figma. So I talked to my boss at the time, you know, Amanda, I said, let's give em a 2nd chance and also when I give her feedback that it wasn't great.

And I want her to come in for 2nd chance if she's interested, I want to see how she reacts because in sales, you talked about earlier it's all about feedback and I need you to be able to take the feedback put it to work and realize that I have your best interest at heart here. So I called her, pretty awkward.

She's not working the team. I'm not her manager. Hey, so wasn't that great, but I want you to come back in. I want to give you a 2nd chance. So she came back in, her whole family is from central California. They have this whole farming business, so she gave 1 of the best demos and Dylan, even said that himself of the product

2nd time around. And she did it all around, like, the farming business. So it's kind of quirky and funny, but she built this mobile app around the farming business. She kind of made it personal and it had so much more passion so much more depth. And it was a showcasing of her true potential and she's come in to the company and thrived.

So, I think that was 1 of the most memorable ones for me, and when you feel that gut instinct, there's someone something special about someone you shouldn't be quick to just kind of dismiss because the interview process is not perfect. Uh, you have this small bit of time with someone you're trying to get to know them as best as you can, make a decision,

it's a big 1. you're going to invest a lot of time and energy and resources, in

this person to be successful. You don't want them to be looking for another job 6 months, 12 months from now. You want them to be at the company 3, 4, 5, 6 years from now.

Brett: For founders who are hiring their first salesperson. What could they learn from how Dylan worked with you over the first couple of years in terms of how he was involved in terms of maybe the details he was involved in details he wasn't. What did you learn from Dylan's involvement in your world that other founders might find inspiration in?

Kyle: Yeah, I think 1 thing that I learned and picked up early on, even in the interview process with Dylan is curiosity, I mean, if you meet him, he's very intense and he's very curious and that curiosity is something you kind of feed off of and for him, it was the network he built where this business is going he is consuming a lot of details.

I think 1 of the biggest learnings, though, and just working with them in our relationship in those 1st, few years was that I actually had to structure what I wanted to share with him. He had never managed a salesperson. And even when he wasn't directly managing me, um, when Amanda had come on to lead all of go to market, I still met with Dylan on a very frequent basis.

We had a consistent one on one, still meet with Dylan today. And I realized I can't just show up. And Dylan's staring at me and I'm staring at Dylan. He can ask me questions, whatever he wants to,. I actually had to build a structure of what I'm going to share with him, what I'm going to update him on. And it's not expected that the founder has to learn how to manage the sales leader.

It's helpful if they do as part of kind of coming to these meetings and feeling like, you know, you can go to the CEO and he can ask you any number of questions. You try and have all the answers ready. May not always be there at the tip of your tongue or may go down a topic that you don't have all the knowledge on that you want to.

So, what I found was like, that's always going to happen to some degree, but I'm going to come in prepared. Here's the structure of the things I'm going to talk to you about consistently, people, process the business, customers, what challenges that we're facing and lay it out to him. And then when I started doing that, we just had way more structured conversations and then going into 1 on 1's

he knows that he's going to get a very consistent update from me. And we'll save time for things that are top of mind or present that day, that week, that month. But I think 1 of the biggest learnings for me being as close as I am to Dylan and I knew drew well, but I was never that close to him in terms of operating rhythm, is that you have to really build the structure to help CEO manage you or like influence you and also to leverage them.

Dylan's great with customers and he's helped us, you know, time and time again. But you have to bring him in and understand how and what is the most leveraged way to do that. And so, in terms of just 1 on 1 and giving him updates and also how we leverage him to grow the business and convert customers,

you know, it probably took 6 to 12 months to be honest to kind of develop a cadence and rhythm and a, operating model that made sense. And I think was a lot more fruitful for both of us.

Brett: Maybe other than curiosity? Why do you think he's been so successful specifically?

Kyle: Yeah, again, I think it goes back to the curiosity when I 1st was interviewing with him it's, you know, I'd hear things around my network. Oh, everyone knows Dylan field. I think he had talked to just about everyone and he was picking people's brains. He's intense. He's sharp. He's got this incredible network and he built that and cultivated that and started doing it

probably what 

18, 19, 20 you know, he famously was an intern before he was the CEO at 

Figma. 

So, I think there's an intensity about him. There's a curiosity about him. And then I'll say the other thing that stands out. There's 2 more things. You could look at this whole wall and he'll point at one small level of detail and he'll double click and triple click and it is a skill set that he has

that's pretty exceptional. I've seen it in product reviews. I've seen it 

in 

stuff that we're doing on the go to market and sales side, and he'll find this 1 needle in this haystack, and he will just drive it home to get all of the questions out that he has. And really surface things that are really interesting that come from that.

The other thing is I've had an opportunity to meet his mom and spend time with his mom and his family, and he just has a really good upbringing and strong moral compass. I think that that can't be taken lightly for a founder and just anyone that you're working and operating with.

Brett: Are there any stories that come to mind of those first couple of years that were critical moments for you as you were building out the go to market function that other people might find inspiration from or learn something that might be useful to their own journey?

Kyle: The reality is that when you're doing something like this, it can be all consuming. You've got to find the boundaries to protect yourself from burnout. I think that, um, the double edged sword of momentum, success, hiring more people and moving fast is that it can kind of become your life.

You're working at this amazing business. You're very fortunate, very lucky, but as an individual, as a, you know, a husband, a father, whatever it may be, you need to find that kind of balance. And so I think for me, a few years in, and it's still something I'm working on every day, every week, but it's just trying to find that balance and learning how to scale what I'm good at and what my super powers are.

And there's always the things that I'll work to get better at, but I think that I've doubled down on really knowing what my strengths are and spending the most time doing that and influencing the team, influencing the business and trying to take breaks and also balance, you know, my time when I'm not working at Figma, because when you're at these startups, you're an early employee,

it's all consuming and that's so positive and so fun and I'm addicted to it. I'll be honest. I love it. but at the same time, you know that being too into any 1 thing is probably not that healthy. So when you get to that point in your career, and you're just thinking about how do I scale myself?

How do I make it so that what I'm known for continues to be there every day, every week? And where I can influence people on the team, customers, the business, be a mentor, whatever it may be, do that. But the other things handoff and as you build and grow the team, you've got more people, more partners, more resources.

And that's kind of a great thing. You just have to kind of change your working style and, and how you stay productive.

Brett: As we wrap up here, would love to hear who are the folks in your career that have had the biggest impact on you and maybe is there like a particular crystallized insight or big idea that you've taken from each of them?

Kyle: I was really fortunate to have some great mentors over the years, and I think that that really can change your career trajectory. So, at Dropbox, I had really great managers and leaders in Oliver Jay, former CRO of Asana, Kevin Egan, who's the current Chief Sales Officer at Atlassian. Amanda clay, who I've worked with over the past 3 years at Figma before most recently reporting to our CRO who is also great.

OJ specifically, um, was a really interesting 1 because his background was a little bit nontraditional. You know, he worked in finance, he'd worked in, venture capital, he went to Harvard business school. And when he joined Dropbox was actually on the strategic finance team. And he just kind of had this knack and interest to want to work on the sales side of the house on the customer facing side of the house and we had this huge inbound sales

team and presence, and we also had a mid market sales team that we're trying to build. And so when he came in, we were actually doing what we talked about a little bit earlier with regards to Figma. We were going from this online inbound sales team and trying to turn that into an outbound sales motion. I mean, he's just brilliant in so many ways and didn't have a lot of institutional knowledge around this sales motion and the sales playbook. It was refreshing. He was thinking through 1st principles, because in many ways, that's all he had and what we were doing at Dropbox was very unique.

Dropbox would have people calling them and they'd be consumer customers to yell about their files being deleted, and all of a sudden you'd have ESPN or, you know, a large bank calling you as an inbound lead. And so we had these really interesting challenges and managing the support queue, converting leads into revenue and business customers and I think, OJ just opened my mind to a different way of thinking and a different way of leading. And I've kept close with him ever since and he's a mentor that, you know, we probably catch up monthly or quarterly at this point.

Brett: Thank you so much for spending the time with us. This was awesome.

Kyle: Yeah, thank you so much for having me, Brett.