This is why I don't believe in sales quotas | Figma CRO

We don't actually have a traditional CS team. We also don't have traditional SDRs. My perspective is quotas are kind of made up.

An average enterprise rep here might have 3 to 4× their OTE for a quota, and we're happy with that. Focus and specialization, no question, as early as possible.

1. How Shaunt Fell Into Sales

Ready to go? Shaunt, it is so good to have you on the show, dude. I'm so lucky in the way that I get to interview the coolest people, and Figma as a product is incredible. The machine that you've built is awesome. I just love to start with you and the love of sales. When did you know that you loved sales? Was there an aha moment when you thought, “This is my career”?

It happened kind of by accident, as I think it does for a lot of people. When I was going to school, graduating high school and thinking about college, there was obviously the sales profession, but it wasn't something you really studied. For me, I fell into it. I ended up going to school at BU, and I was studying advertising.

We had to get a summer job, and I remembered that, just the year before, I had gotten my very first cell phone. This was back in 2000. Cell phones were becoming a thing. You didn't have them when you were much younger than that.

I remember when I got my phone. It was in a mall, in one of those kiosks, and I remember asking the woman who worked there, “Hey, how did you get this job?” She said, “Well, I'm a law student, and this is a way to make extra money, and you can do really well.” I thought, “I wonder if I could do that.”

I went to the same kiosk in the mall where I bought my own phone with my mom the year before, and I met this guy who was working there. I said, “Hey, how does one get a job like this? I have no idea, but I'm home for the summer. I'm looking for work.” He said, “Why don't you start by writing down some information here about yourself?” He gave me this piece of paper. I wrote down my name, my address, and my phone number.

He said, “Okay, great. You start Tuesday.” I said, “What do you mean?” He said, “Yeah, cool. You're hired, man.” I showed up Tuesday, and he handed me some pamphlets. He said, “These are the phones you want to sell, and you make money. These are the ones you don't want to sell. No one cares about the phones. You sell whatever is in the bin. Go to work.” Then he left. I thought, “Oh my God.” I started figuring it out.

2. The #1 Trait to Succeed in Sales: Curiosity vs. Being Prescriptive

Going back, knowing all you know now, if you could call up that boy with those cell phones and give him one piece of advice on how to be successful in sales, what piece of advice would you give?

The first thing that jumped into my mind was: be curious, and really try to understand the person that you are trying to sell to. What's their situation? What's their circumstance?

Do you have the time today to be curious? What I mean by that is people are very cautious and hesitant about giving their time to anything. It's more like, “Shaunt, I know that Figma is this-size company with this X and this problem.” Do you not need to know the customer today because you don't have time to be curious? If you're going to do qualification on me, dude, I don't want to be qualified. You should [__] figure it out.

I do think it's a skill. To be honest with you, I believe right now, more than anything else, if you want to be great in enterprise tech sales, it's not just about being curious; it's about being prescriptive. That's an interesting balance, right?

You're right, people are busy, and what they really want is insights. They want to know: what can you teach me? What are your other customers—your best customers—doing that we haven't figured out yet? That's very much what we are preaching to our sales team every single day. But you have to mix curiosity in along the way. I think that's the art of it: you have to be able to do both at the same time, or else you're not going to be successful.

3. Is Sales Less Important in a PLG World?

When you look at Figma, it's a beautiful product, and it's a PLG motion in so many ways. In a world of PLG, is sales less important than ever?

I don't think so. But what's really unique about Figma as a company is this: I joined about 4.5 years ago, and I started talking to Dylan 5.5 years ago. At the time, it was really early in the journey, but it was kind of unique in that Figma had been around since 2012 and had really spent 6 years building the product, studying customers, and trying to perfect it. That was really not something that I had heard happen very often.

Then, once you started monetizing—this was around the end of 2017, end of 2018—it really took off. It took off very much in this—not even PLG, I would say self-service—way. Most of our customers, even today, at some point started by going online with a credit card. Someone bought a couple of licenses, started sharing links internally, and that's how things took off.

That happened really fast. When I joined 4.5 years ago, we were a hundred, maybe 50 million dollar company, but in terms of our penetration in the market, we had tons of customers—way more. I joined Datadog, my previous company, at a similar stage in terms of revenue, but nowhere near the number of customers.

In many ways, the job at Datadog in the early days was much clearer than it was at Figma. At Figma, we had acquired all these customers so quickly, and at the time, to your point, mainly what people were doing on the sales side was PLG. The sales role 4.5 years ago was almost exclusively calling into or responding to existing customers that were on self-service plans, and all we were doing was upgrading them to the higher tiers of the product. That was the motion.

4. How Figma's Sales Motion Evolved From PLG to Outbound

Fast-forward to today, and it's very different from that. We are global, and we have multiple segments: SMB, mid-market, enterprise, and strategic. If you look at what most of our sales reps are doing, especially mid-market and above, it's very sales-led. The PLG motion of upgrading people to new tiers and expanding seats into the existing accounts is still there, but so much of what's happening is actually what we were talking about before: being prescriptive and going into the customer with insights.

When you say sales-led, you mean it's outbound?

Oh yeah, 100%. Not 100% of our business is outbound, but in terms of what the sales team is doing at Figma, it's majority outbound today. It's outbound, though, into an existing customer base. That's the part that's unique.

These are companies that are using Figma, but they think they're happy using Figma. They've figured out how to use us in a particular way. Through curiosity and understanding patterns from how other customers are using Figma, we are approaching them with proactive insights for how they should be thinking about doing more with us.

Who is responsible for that? Is that account executives? Is that CS? How do you structure responsibilities on the team when you have that?

We don't actually have a traditional CS team. When I started, we had a lot to figure out in terms of what the motion was. What we realized was, coming back to that earlier premise, most of our customers found us through a website and a credit card, and they made their own decision on what they thought the value Figma could deliver to them was.

If you look across our customer base—and this is even true today—and compare what an average customer is doing with Figma to what we think they should be doing with Figma, there's a pretty big gap and a pretty big discrepancy. Our job was to figure out how to go and proactively educate the customer on more of what they could be doing.

We asked ourselves: is that a CS function? Is that an account-management function? But where we landed is, for the most part, that is a hunting motion. In order to be successful doing it, you have to go in and, in some cases, get existing champions, but in a lot of cases, new prospective champions and EBs, to be really excited about something new that they haven't learned about Figma before.

What is the primary role of those, generally speaking? Is it product expansion? Do we want the same people to use more, or do we want more people to use the same product? I know it's both, but if there was one more?

It is both.

But if there was one more?

Honestly, it is both. For the most part—and by the way, this has evolved, too, as we've gone from a single product to multi-product—I would say right now it's probably a little bit more on the using-new-products side. It could be the same people using those new products, but oftentimes we're talking about new personas, getting new individuals exposed to some of the things that we have to offer.

When you think about going multi-product, I very often have companies that go multi-product that I'm invested in, and the reps honestly know that vertical solutions are better at point-solution things. That's obviously not the case with Figma, but what would you say if you know that your product is not as good as the vertically focused one, but you're selling the platform?

I don't know that I have that exact situation that you presented, but I think you're saying: if the power is the platform versus the specific features and functionalities of your one particular product, yeah.

I think, frankly, the best sellers are not the ones that are focused on how this feature is better than this other company’s feature in this product. I think they are better at understanding where a company is trying to go, where their business is trying to go, and connecting the value to the overall solution and to those things that they are trying to accomplish. There’s a storytelling aspect, and there’s obviously the curiosity that we’re talking about there.

But I think you have to be generally just honest with yourself about where the customer is really going to get the most value from what you have to offer compared to the competitor, right? If that is through the point solution, then that’s what you’re focused on, and I still don’t think you use feature and function to get there. I think you focus on value and value drivers. But if it’s the platform, then that’s the narrative that you want the customer to believe in.

5. Is the Seat-Based Pricing Model Dead?

When we think about that platform expansion and product expansion in terms of usage, everyone is saying that seat-based pricing is dead. Seat-based pricing—do you agree? And if so, what comes next?

I haven’t seen anything in our business that would suggest to me that that’s the case. I think it is hard to predict the future on this one, honestly. But if you look at our own business, we had our earnings call a couple of weeks ago. You may have seen it. We added 5 points on our net retention, which is pretty significant. We went from 131% to 136%.

Obviously, today, we’re in a pretty much exclusively seat-based model. Now, you might also know that that’s changing in just a matter of a few days, where we’re going to start monetizing our AI usage through credits as well. But so far, we haven’t seen that in our business. Part of that, I think, may be just the fact that, because of all the things happening in the world and in technology, there are just more and more builders coming into software as it exists.

Is that part of the reason? I don’t know. But there’s nothing that we’ve seen in our business yet that suggests that’s dead. I do think it’s a tough one to predict long-term.

Well, I think it’s because your business is predicated around product people and designers. If you’re in customer support, you can’t have a seat-based business. You’ve got to have an outcomes-based or a consumption-based model in a lot of other businesses where you’re replacing labor. If you sell seats and you’re replacing labor, you’re in a tough spot.

Yeah, that makes sense, right? I’m just not as knowledgeable about what’s happening in those other BUs. From what I can see in our business and the people we’re selling to, that doesn’t feel like a thing that we’ve encountered yet.

6. Does the SDR Role Still Have a Future?

Totally get that. It’s an interesting kind of pushback on the traditional narrative. Another aspect that I see more and more is the destruction of the role of the SDR.

Mhm.

Does the role of the SDR survive in 2 years’ time, or will the AEs just be completely responsible for pipeline generation, PG? How do you think about that one?

Well, I’m smiling because we also don’t have traditional SDRs. We really tried to be first-principled with how we built the go-to-market at Figma. By the way, this is coming from someone who had, by the time I left my previous company, maybe 200% SDR team—a pretty traditional one.

Here’s what I’ll say. First, SDRs or not—and you probably know that you spoke to my former boss at Datadog, Dan—AEs have to be responsible for their own PG. Full stop. I think that’s consistently true anywhere I’ve been, and I firmly believe in it. I think that’s critical. That is the job in a lot of ways, and the most important part of the job.

With SDRs, I’ve always tried to be really thoughtful about where the SDR is actually adding clear incremental value in a business where you expect AEs to PG as well. Honestly, anywhere I’ve been, it’s always been a little bit challenging to really isolate: What did the SDR do versus what did the AE do? Do you have them share accounts? Do you have them split and have the SDR work on some and the AE work on some? It’s hard. Honestly, it’s hard, and I think I’ve always struggled with it.

At Figma, there’s this other unique aspect, which is, again, our problem is not acquiring new customers, right? We have a lot, and so much of our focus is on how we expand in those customer bases. And yet, even having a lot, what we’ve been trying to figure out is: What is the job that needs to be done?

We’ve tinkered with SDRs partnering with AEs to expand into specific personas and do things like that. But recently, we made a new shift and said that even that was something we were going to take the focus away from. We’re using them now in a more pointed way on existing customers and managing small, transactional renewals to get those off the plates of some of the more strategic AEs and the strategic work we want them to do.

So we’re always tinkering with what’s the best way to deploy that resource to get value. And then, of course, they’re our talent pipeline as well.

They’re our future reps. So we have no SDRs and we have no CS. Just so I understand, the sales team is structured with AEs. What else do we have in that?

When I started, it was basically that we had AEs and AMs. We had 2 segments: mid-market and enterprise. If you looked at what mid-market and enterprise were doing back then, it was effectively the same thing. They were doing PLG and upgrading people. It was a single-product company.

Then AMs were effectively doing CS-type work. They were driving seat expansion, but really, they were doing support and trying to be really responsive to the customer. It was necessary at the point in the business we were in.

7. Why Focus & Specialization Is the Key to a Great Sales Team

When we looked at it, we said, “Okay, what do we need in the future?” One of the things I believe in the most is that you need to have focus. The best sales teams are the ones that are really, really focused and specialized. If you’re asking a rep to do 14 different things, it’s too hard for them to be good at all of those things.

So we looked at our business and said, “Where are there places where we can create focus?” The first thing we realized was, let’s isolate this PLG motion. When we looked at it at the time, where was the PLG upgrade?

When I say PLG, by the way, maybe to define this for everyone, I think of our business as 3 distinct businesses at Figma. One is self-serve. That is, people go on the website, they put in a credit card, and they buy what they think they need. You can buy our lower-tier plans directly through the website. Then you get a link, you send it around, and you grow.

Then we have what I’d consider our PLG business, which is really concentrated in our SMB, what we call our SMB segment. Those are reps that are covering 0-to-500-employee businesses. Then we have our sales-led business, which I’d consider mid-market, enterprise, and strat. Those are basically smaller book sizes and smaller companies. So that’s the way we’re set up right now.

That PLG motion, we said, “Let’s isolate it to SMB,” because we looked at the companies that were typically in that position to be upgraded from self-serve, and almost all of them were under 500 employees. Basically, they were new startups coming into the ecosystem. They were buying licenses themselves, and then we tried to be really sophisticated around when the right time was for us to proactively reach out to them based on product signals and the maturity that we saw happening, to then have a conversation about, “Okay, you need to move up tiers.”

8. When to Intercept a PLG Customer and Convert Them

I’m a founder with a PLG motion. What is the 1 piece of advice you would give me on the right time to intercept? It could be duration, it could be usage, it could be seat expansion. What is that sign?

I don’t think it ever hurts to do it a little earlier than a little later, because what we do still find is that, even when we think it’s the right time based on our formulas, you still have to convince someone that that’s the case. That might take a couple of go-rounds.

Our SMB team will often lose a deal—as in, an upgrade transaction—and then they’ll win it a couple of months later. That’s very typical; it was typical at my last company as well. But I think the answer is dependent on so many factors around how people are using a product, which features you’re gating, and how they’re interacting with it. I don’t know if there’s 1 specific answer to that.

When your business is basically expansions and upgrades, do you have pipeline reviews in the same way?

Oh, yeah. So, by the way, just to finish, what we did is we said SMB, and that’s the PLG motion. Everything else is sales-led. Everything else we do—mid-market, enterprise, and strat, which is the majority of our team and the reps that we have—is running like a very traditional SaaS sales business.

Again, what’s unique is they’re PG’ing primarily into what you would consider to be a customer. We almost don’t think of it that way, right? The job of a sales rep is that they get their book of accounts. Every year, we create more focus around them, and we’ve had to do ruthless prioritization on which accounts we’re going to really go deep on.

But once they get their accounts, the job is: You map it out. You map out that org, and you basically have a vision of what a best-in-class deployment of Figma looks like based on your understanding of this type of business. Where are they today? That gap between those things is your job, and you need to go figure out how to do discovery, how to do new business meetings, and how to build champions to get them to go from where they are to that future state that you want to bring them to through insights and a point of view.

And that is 100% what we do. They do PG, they create opportunities, we do pipeline reviews constantly, and we do forecast calls every week where we're digging into it. Nothing is super unique in terms of how we run that part of the business, except for the fact that it's not traditional net new, which is a definition a lot of other companies would use.

What's your single biggest piece of advice for how to create champions on steroids within a customer base?

There are a few things. First, you have to bring them insights—insights that are relevant to what they do and what they're thinking about. That value, I think, is the biggest thing that makes a champion go, “Okay, I'm all in.” It's not just, “I love your product.”

Of course, the Figma community is incredible, but if you want to build an enterprise champion, educate them. Teach them something they don't know that's going to make them and their teams more effective at their jobs. That's the first thing that comes to mind.

9. How to Think About Sales Quotas

I totally get that. That makes absolute sense. When we think about teaching them and converting them, I think sales comp is a very hard thing to get right. We just had the CRO from ElevenLabs on the show, and they have a 20x quota. Is that a new world of PLG, or is that ElevenLabs-specific? How do you think about the right quota setting?

I've got, I would say, controversial opinions on quotas in general.

Go on.

My perspective is that quotas are kind of made up, honestly, and I say that all the time to my team. I think there's this prevailing wisdom with quotas that I've seen, especially when you're going into planning and trying to map out your year, where you go, “Okay, how much ARR do I need to generate? How many people do I have? How much quota do I need to dish out to feel like I've got enough coverage? If we're trying to add $500 million next year, and I've got $600 million of quota out there, that means even if people end up at 80% attainment, I'm good.” I just think that's made up.

I don't think that has anything to do with how people are actually going to do. The way I think about quota is that it's more about a philosophy you're trying to implement around what work needs to be done and how much reward you want to dish out for that work. I think it generally comes back to that, so I don't have a singular philosophy.

Can we talk—if you don't have quota, or don't believe in quota, how do you think about setting urgency and setting incentive?

I believe in quotas. We have quotas. What I'm saying is that I don't necessarily believe you completely de-risk your year by making sure you've dished out enough quota to cover your target. I think that's a bit of a false sense of comfort.

What I believe is that, with quotas, you want to try to determine what you're trying to accomplish. The way I think about it is that I don't think there's a single answer, and I think even at Figma, we've evolved. In the early days of Figma, which may be similar to what's happening at ElevenLabs right now, the job was primarily to take this product, make your customer really happy, know the product really, really well, support them, and then viral expansion would happen.

Frankly, if you think about the job to be done there, there's a pretty wide population of people who could likely do it if they came in and cared about learning and the product, et cetera. That's one thing. If you have that business, you have to think about what the reward is for that and what the population of people is that can do that job.

But isn't that job quite easy? You're essentially an order taker. When people are pulling the product out of your hands and desperate to use it, it's kind of easy, no?

I think there are things about it that are hard. I don't want to say it's easy, but the way I think about it more is: how many people out there could probably do it if we brought them in, trained them, and they had the right personality and the willingness to learn?

I think there's a big population of people. You don't need to have 20 years of sales experience to figure out how to do that, even if there are things about it that are challenging. I don't want to diminish what the job is, but I think in that type of situation, you're probably focused more on driving efficiency in the business.

10. Why Figma Gives Reps Low Quotas for Hard Strategic Work

Where we are right now, in that SLG motion in particular—which is, again, mid-market, enterprise, strategic—what we're asking people to do is the stuff you just heard me get so warm and fuzzy about when I heard customers talk about bringing insights and building champions. That is strategic work.

You need people who can really understand how businesses operate, who understand not only the product but the landscape we're operating in, and who are able to do PLG, build these relationships, bring these insights, and manage complex, multistakeholder deals. That is hard work, and it's very, very strategic work.

Our philosophy now at Figma is kind of the opposite. We want to have really aggressive—as in relatively easy—quotas compared to what's out there as an industry standard, because the work is hard and strategic, and we want to really reward people who are doing that great work.

We also realize that the population of people capable of doing it is smaller. They need more experience, and they need certain qualities and attributes. Again, I think what ElevenLabs is doing is probably perfect for them. I'm on the opposite side of the spectrum right now, where I want people to feel like Figma's a place where you can come in, do this hard, strategic work that's really driving value for your customers, and then be outwardly rewarded for it. An average enterprise rep here might have 3–4x their OTE as a quota, and we're happy with that.

11. Deal Experience vs. Industry Experience: Which Hire Wins?

You can have someone who's sold that size of contract before, or who's worked in or around the industry problem area that you solve, but you can only have one. Which one do you have, and why?

If those are the 2 options to choose from, I would take the person with experience doing the deal, because I think industry experience you can teach to the person who's got the right willingness to learn and the curiosity. Obviously, you need to make sure you have that in a person, and you test for it.

I'm making a bit of an assumption that, with those 2 choices, the person who's done the really big deal hasn't just got a bluebird, right? They've managed multistakeholder, long sales cycles, had to build a lot of champions, and had to get to EBs. They're likely leveraging something like COM, using MEDDIC, and familiar with these concepts.

12. What Shaunt Looks for When Hiring Sales Reps

I think there's a lot more confidence that needs to be built over time for people to be really good at that. Generally speaking, smart people can learn industries and landscapes in a shorter period of time. So, if those are my only 2 choices, I would probably take the person who's got the deal experience.

When we're running a process now for hiring people, how has what you look for in sales reps changed over time?

I don't know that it's changed that much, to be honest with you. The first thing is what you see on paper, right? I think that matters, and increasingly I've become more opinionated on what I'm looking for there and what I'm not.

I have to admit, some people don't agree with this, but I usually have a pretty visceral reaction to people who are super jumpy in terms of a résumé.

When we say “super jumpy”—I know it sounds awful—but this is 1 year, 1 year, 1 year.

Exactly. Like 12 months here, 18 months here, 12 months there. Again, there are so many reasons why people would encourage me to have more of an open mind about it, and I get all of that. But generally speaking, when you're doing this at scale—

I don't, I don't, I don't. It's total bullshit. If you've done it 4 times—

Right. It's saying something.

Yeah. Once, it could be culture, it could be family, it could be whatever. But 4 times?

Yeah, yeah. So, when you're talking to someone, it's a lot of the obvious things, right? Can you learn from them that they have the grit and that they're willing to persevere? That's a really important one for me.

How do you tell?

Oh God, it's so hard. I don't know.

It's really hard.

It's really hard. I think what Dan would tell you—and I think he mentioned it when he spoke to you—is that he really wants to get the full history of the person, going back to their school days and how they made their decisions. I will do that from time to time, but I don't always do it.

Frankly, the thing that tells me the most on that front is the résumé. Looking at the places they were and having a sense of the arcs of those places when they were there, is this someone who was just chasing something that was easy, or were they really sticking with something and making a success out of something that wasn't successful? I think that's a big part of it.

You can even create a process that forces perseverance through it in terms of an interview process.

So, we always make people do a challenge or an exercise at the end that requires some heavy lifting in terms of learning a bit about our business, but also showing off their basic sales skills around discovery. I think that’s a way to do it, too, but it is hard. It’s hard.

What is the challenge or exercise? Is it a take-home assignment?

It’s a take-home assignment. We’ve evolved it over time, but it’s a combination of a discovery demo. Basically, we want to give people a use case, a case study: you’re going to go pitch to this customer. Here’s some information about them. Learn about them and come in prepared to lead a conversation, do some discovery, and then turn around and get in the product a little bit and show us a quick workflow that you think would be interesting.

Personally, I’m much more interested in how they do on the discovery side of that, because I think it’s probably a little bit unfair to expect someone to do this amazing demo of your product with just a few days of playing around with it. But I do think we’ve kept the product piece in there because it shows an element of perseverance. If someone is actually willing to spend the time to learn a little bit of it, I think it’s telling. The way they approach the discovery part tells me a lot about their ability to actually be curious and do all of those things.

Okay, so you and me are really impressed with this candidate, and we’re thinking, “Great, we should hire them.” We move to the offer stage. Is there anything in the offer stage that gives you green lights or red lights around a potential sales hire?

One of the things that I always try to do is back-channel. I think that’s a little bit outside the question you’re asking, but getting signals outside of the process is, in some ways, one of the most valuable insights that you can get on someone. On the offer stage itself, you have some people who are naturally going to negotiate, and you’re going to have people who are not. I don’t necessarily make strong judgments there, because I actually think oftentimes the person who isn’t negotiating at the end isn’t negotiating because the hiring manager and the recruiter have done a good job of positioning ourselves and our offer in a way that makes them really happy to jump in and take it.

The biggest thing I’m looking for at that point is that someone has to be all in. They have to be really excited to come on board. I understand that people have choices, and I fully respect going through a process with multiple companies. But if, at the end of a process with Figma, after spending a couple of weeks doing all this work, you’re not saying, “All right, I’m in. I want to do this,” it tends to be a bit of a yellow flag for me.

If they’re actively trying to pit you against another company, I get nervous, because we’ve seen some people we’ve hired like that. As soon as things are tough, or they didn’t have the initial success they expected, or that other company that maybe they didn’t tell you they were actually more excited about came back with a better or different offer, they leave. Do all the investigation you want to do during the process, but by the end, both sides should feel like they’re all in on this candidate.

13. Slow Hire vs. Fast Hire: Which Is Better?

What do you do when you have to ramp a sales team hiring plan fast? Is it better to fill seats and, bluntly, get rid of them fast and be quick with decisions, or is it better to go slow and miss the hiring plan?

Between those 2 choices, I would prefer to go slow and risk potentially missing the hiring plan. If you make the wrong hire, it doesn’t matter how fast you move—you’ve cost yourself time, in my opinion. It’s a balance, but at the end of the day, if someone comes to me and says, “I know I’ve been sitting on this open headcount for 3 months. I have someone I’m not that excited about. I think they could maybe grow into a solid B player,” I’m never going to say, “Hire that person.” I’m just not going to do it, even if it risks the hiring plan.

I met a founder yesterday who was increasing their sales team by 200 reps over the next 12 months.

Yeah.

I was just like, “Honestly, how many do you think will be good?”

Yeah. And he was like, “Probably 20.”

Yeah.

Yeah. I mean, the flip side of it is that there’s a reality to it. It’s slightly different from resigning yourself to hiring a C player, but I think it’s facing the reality that you can build the best process and have the best instinct, and I still come back to the little joke I made earlier: really figuring out if someone’s great in the interview process is actually freaking hard.

You have to realize that only part of the job is getting the person in. That’s when it really starts, when you have to figure out whether you have someone who’s going to be able to grow and be successful, or whether you made a wrong hire and have to do something about it.

I also think that it’s not always as simple as right hire, wrong hire. I personally think most people have the potential in them. Some don’t, and you might make some mis-hires, but a lot of people have potential. There are so many factors that contribute to whether they’re going to be successful or not: how great is their leader, how great is the enablement, and how much of a chance did you actually give them?

I’ve got people who’ve gone on a performance plan. This person I’m thinking about, actually from my last company, went on a performance plan and was really struggling. But we kept looking at all of their inputs. There were so many great things they were doing, and we said, “Let’s focus on just coaching around the areas that are gaps.” They came off of it. I’m long gone, but that person is still there, has had multiple promotions, and is one of their most successful reps.

I actually think it’s not as simple as whether you hired the right person or the wrong person. It’s whether you put them in an environment where they can succeed and whether you’re actually holding them accountable to the right things.

Can I ask you how big your sales team is today?

Hundreds. We’re probably pushing 500 in my whole organization. That’s not just sales quota carriers, but if you include some of the supporting resources, et cetera, yeah.

Will sales teams be larger or smaller in the future?

I think we’re going the opposite way.

I’m still pushing you to be more efficient.

We talked a lot about efficiency in our early days. First of all, how much more efficient can you get? You’ve got 500,000 customers you’re trying to support with, I don’t know, 300 quota-carrying reps, whatever the number is. You’re already pretty freaking efficient.

I think this might be a unique Figma thing, but for us, I’m pushing—and Dylan is on board—with more headcount in sales to do more of the strategic work with customers, and we’re really seeing great results from that. Is that the case for every business? I don’t know, but it’s the case for us. I think we’re going to continue investing in sales headcount.

Going back to the hiring process, when you’ve made a mis-hire, what did you not see that you wish you’d seen? For me, one is when I’m constantly pushed by the candidate on role and they want an increased title.

Yeah.

14. Mercenary vs. Missionary: The Red Flag He Always Misses

I always push back. I’m like, “Well, they’re brilliant, so of course they want to be a VP.” No, no, no. It’s always the problem, and it always ends badly. What’s yours?

I think it’s anything like that that suggests mercenary versus missionary. We’re all in sales, so there’s a little mercenary in all of us, and I get that in some ways that’s what the profession calls for. But lots of my best people over the years weren’t thinking about money first.

Career growth, learning, and development are different. That’s very, very different to me. I think the best people know that if you’re prioritizing those things, the money comes. In fact, some of the people who’ve been the best earners that I’ve been around in the past 10 years haven’t been the ones who were focused on, “I’ve got to maximize my W-2.” I’ve seen people who, when they’re chasing that, it goes the other direction.

That’s probably my answer. There needs to be a passion for growth, career acceleration, learning and development, and collaboration from people who want to just get better. The growth mindset, I think, is the biggest thing. If people are too focused on things that aren’t suggestive of growth and are more focused on the individual and this very point-in-time thing, that’s a yellow flag for me.

15. How to Ramp New Sales Reps Effectively

Okay, so we make this hire and it’s time for them to ramp. I’m a founder, and you’re an angel investor in my company. I’m sorry, you’ve probably just burnt your money, but go with me on this journey. How do I ramp new reps effectively? What would you advise me?

It’s a good question. I think we’re always learning on this one, so I won’t admit that I’ve perfected it, or that we’ve perfected it, or that anyone has perfected it, because I think it’s really hard.

I always come back to first-principles thinking: What do you need? What does your organization need at that point in time, rather than just a simple formula that's rinse and repeat regardless of the situation?

I would think about what the job is that needs to be done by that person. I say that because, even in our own organization, we're thinking about whether the onboarding and enablement plan for an SMB rep who's primarily doing the PLG motion should be exactly the same as that for a strategic rep who's got 2 accounts or 1 account that they're trying to go really deep in. I don't necessarily think that it needs to be the same.

Ultimately, I play back: What do you need this person to do? What do you need them to be really good at? How do you get them enabled in those things as quickly as possible? Is it that they really need—

Take me to a strategic rep. Take me to an enterprise rep and give me that onboarding.

For an enterprise rep, one of the things we want to do, as quickly as possible—even before we teach them all the product stuff and the sales skills, which hopefully they're bringing some of with them—is get them into their account and their territory.

The first thing is to throw them into the fire. You've got 1 or 2 accounts, and these are accounts that are spending a lot. There's so much work to be done. Before you came in, likely there was another rep working on it, or the manager or director is talking to them. Let's get you engaged, having conversations, building relationships, and learning that business.

After a couple of weeks, they've gone through the initial process, they've got their laptop, they understand what account they have, and they've maybe been on a few calls where they've listened in. Now we want to get them into proper onboarding.

The way we think about that is: What are the things that this rep needs to know to be really good at their job? A strategic rep in this example better understand the landscape really well. They need to know the product, obviously, and our platform, but even more so, what is happening in tech around our ecosystem?

Do you create a playbook for them on that? Is it a file of facts that says, “Go learn it”? How does that work?

To be honest with you, we're rebuilding this right now. We're rolling out—we actually did this week—a soft launch of the new version of it, but that is what we're striving toward.

We're also moving to classroom-style, in-person training. In the COVID days, we got away from that, but we're going back to classroom-style and in-person training. We're bringing in the thought leaders across the organization and across these different pillars.

Absolutely, we're going to educate them on what's happening in the tech ecosystem, the different players that their customers are going to be thinking about, potentially using, and leveraging. Here's our positioning in that conversation, here's what our best customers are doing, and here are the things you need to understand about the product.

Then, of course, here is our sales process. They need to understand our sales process from beginning to end, all of the resources that are available to them along the way, and all of the things that we're going to do to help them: pipeline reviews, forecast calls, and the operating rhythm that we've built here.

It's taking them through all of those things once they've got a little bit of footing underneath them, and then it's ongoing enablement. If something new happens in the market, how do we make sure the whole team is educated on it?

We have recurring enablement stand-ups where it's, “Okay, something new happened,” whether it's a product launch on our side or something launched in the ecosystem that we think is important to keep people updated on.

What sales communications platform are you on? When you think about it as a team and there's an update in the market, is it Slack? Is it email? How do you ensure synchronicity of knowledge across teams?

I think, honestly, we have work to do there. If you talk to our reps, it's one of the things they complain about, if I'm being completely honest. We have room for improvement because we use it all.

We have our sales enablement platform, then of course we have Slack, and our Slack is noisy, as are a lot of the other companies that get to our scale. We're doing things in person, we're doing things on Zoom, and we have content everywhere. We have so many customer stories that they end up in multiple systems.

Of course, we have our CRM. I think we have more work to do to make searchability better across all of these different places, or to just say, “Look, we're going to take a different approach. We're going to have everything go to one place and have a single source of truth.”

We don't have that solved yet. I'm being honest.

How do you think about pushing the boundaries of sales technology adoption within the team? Jason's one of my best buddies. He is so versed in Qualified, Momentum, Artisan, and all the different providers.

Yep.

Do you worry that you're too focused on execution, that you don't pull your head up enough to invest in the future of sales tools?

I do worry about that, if I'm being honest. That is not something that has been top of mind for me historically. I've been much more focused on the inputs: What are we doing every single day? How are we getting better ourselves? What are the conversations we're having with our customers?

But to your point, in these last few weeks and months, I've been much more passionate about where we can invest more in either agentic solutions or more exciting tech that can make some of this stuff easier.

It just comes back to wanting to make the job of our reps easier. It's very clear where they're really happy and where there are frustrations. I think every company is going to have both.

The frustrations on our side right now come from the fact that there's a lot on their plates. If we can leverage some of these new technologies to remove some of the friction around the duplication of data entry and those types of things, I think that's not a hard thing to do, and it will make a meaningful impact.

I didn't mean this badly, but do you think you and the team are equipped to train agents in the way that they need to be trained? Again, I go back to Jason. Jason is so good now at training agents, and he assumes that everyone else is. I don't know many sales reps who are that versed in how to train the next generation of sales agents.

I don't know that we are. That's something that we'll need to explore and figure out—whether we're capable. If not, we're going to have to learn how to bring in more resources and knowledge on that subject. It's certainly not something that I'm an expert at personally.

This is why consulting businesses will do very well in the next few years, my friend. Seriously. Implementation and adoption, I think, will be one of the biggest things that you can learn and improve on as a company.

You mentioned sales performance and hot takes there. What are the hot takes around sales performance? I'd love to hear those.

Probably my hottest take on sales performance—which is not a new thing; I've said this for a very long time—is that I don't really care if you, as a rep, hit your quota or not.

What I mean by that is a bunch of things, but first and foremost, similar to the discussion we were having before, I think I've been in situations consistently where we're doing our best to set a quota based on that philosophy. I just shared our philosophy right now: to try to do aggressive ones and really reward people.

I've been in other situations where we're focused a little bit more on efficiency, based on the job to be done. Whatever the philosophy is, I've been in situations multiple times in my career where the year starts going, and you realize you didn't actually get it right.

That could be in either direction, right? You set them too high, or oftentimes you set them too low. Whatever you expected, you don't get it right. I think of quota as both something that's more systemic than something that's entirely on the individual.

The other reason for this is I just think it's too much of a lagging indicator, and my fear is that it creates lazy leadership. If we're performance-managing based on the idea that someone got to their number or didn't get to their number at the end of a month, quarter, or year, then if you're a strategic rep, we don't really know how to judge you until the year is over, right? If you have 1 account and you're building toward this big renewal at the end of the year—

Then how do we judge people if it's not on quota? How do we judge them?

I am obsessed with behaviors and competencies as the core facets of a performance framework.

Okay, but then how do we make that specific—behaviors and competencies?

You write it out. We have written out—and, by the way, it's probably, if I'm being honest, maybe too detailed—a performance framework.

One of the first things that we did is write out a performance framework and say, “By the way, quota is part of it.” There's a results category, and I'm not dismissing quota entirely, but there's a results bucket, and that's just 1 bucket.

And that is not just results from a quota perspective. It's PG, it's all of the success metrics that we are tracking. Then there are behaviors, and we documented what that means. And then there are competencies, and we documented all of the competencies that we actually care about.

Just dig into what behaviors and competencies are, because if you have “curious” and “ambitious,” dude, I can be curious and ambitious and sign no fucking contracts.

Yeah. I think the behaviors one is probably a little bit simpler and more straightforward. How are you showing up? Are you collaborative? Are you lone-wolfing it, just looking out for yourself? Are you collaborating with your teammates? Do you have a growth mindset? Are you someone who’s constantly negative in the office and impacting the people around you? There are some basic things there.

Competencies, which I think are the most critical, are: If these are the things that we’ve defined as important for you to be good at your job day to day, what are they? That’s the ability to do PG effectively. That’s the ability to do discovery effectively when you’re talking to a customer. That’s the ability to actually manage your pipeline effectively, leveraging our MEDDIC framework. When you’re doing discovery, we teach CALM. We call it Figma Value Selling, but are you leveraging our methodology when you’re doing discovery? So it’s all of those details.

Then, back to the point around the hot take on quota, where I come back to is this: If someone says, “Hey, this person is not doing well,” the first thing I’ll ask is why. If they say, “Well, they didn’t hit their quota,” I’ll immediately go, “Okay, well, let’s talk about why they didn’t.” Let’s get into those competencies and behaviors.

If someone says, “Well, actually, this person is totally busting their butt and grinding. They’ve got an amazing work ethic and a great attitude. Every day, they’re trying to get a little bit better. And, by the way, their PG is really good, and it’s just taking some time. It’s not translating yet. When I listen to their calls, they’re executing calls really, really well, and pipeline is being developed. It just hasn’t translated to their number yet,” my argument is: If you’re going to move that person out of the business, what are you hoping to get to take that person’s place?

Okay, if you’re doing PG really well and you’re doing qualification really well, and you’re showing up to the calls, you will convert. It’ll convert.

I agree, with the exception of: What if we got it wrong? What if we got the quota wrong? What if we set it too high? That happens. It truly does. I agree with you, Harry, but we’re trying to manage things at scale, right? What I don’t want is to create a culture of lazy leadership.

I want leaders to be in the details. I want leaders not to be saying, “Well, I’ve got to move this person out because they didn’t hit their quota.” I want them to say, “It’s because this person isn’t showing up right. They’re not working hard. They’re not capable of translating our enablement into conversation.” That tells me the leader is in the boat with the rep. They’re not lagging indicators; they’re more real-time.

16. Is There a Place for the Lone Wolf Rep?

I’m a lone wolf, but I make a lot of money. I close, and I’m not bad for the culture, but I’m not collaborative and I’m not a team player. Do you have a problem with me?

I think there’s a place for that, honestly. I know some great reps whom you would probably define that way. Actually, when you talk to them about it, they don’t even want it. It’s not like they’re proud of being a lone wolf; it’s just how they’re wired, and the job means something different for everyone.

I don’t really have a problem with that. I’ve seen people who are categorized that way, and once you talk to them and say, “Hey, buddy, you’re great, but some people are defining you as a lone wolf. Is that how you want to be known?” they go, “Oh, fuck no. I didn’t even know that’s what people thought of me.” They say, “Thank you for the coaching.”

There are others who say, “You know what? I’m going to be a lone wolf, but I promise I’m not going to poison any wells. I’m not aspiring to be a leader. I just want to do my thing, make money, and be successful.” I think that’s also perfectly okay, as long as it’s not negatively impacting others.

That was one thing that I’ve really allowed: bad apples to persist because they’ve made money, and I’ve forgotten how damaging it is to the rest of the apples.

That is a different situation. That is a problem, and I think you can’t move fast enough in those situations. I’ve seen them—we’ve seen them at multiple companies I’ve been at—and you can never move fast enough, in my opinion.

I will say, sometimes I don’t know that they know. Even in those situations, I do think you start by giving feedback and coaching. Sometimes you’ll find that people are like, “Oh, wow, I didn’t realize I was coming across that way.” Other times, it’s very apparent and it is more malicious.

I still feel like you give the feedback and coaching, but if it’s still persisting, you have to make a move.

We were kind of aligned, actually, when we were talking around quota. You said, “Well, sometimes you just set the wrong quota.”

Mhm.

17. How to Set Quotas at an Early-Stage Company

If you’re advising another sales leader—or me, a founder of an early-stage company—on how to set quotas effectively, it’s pretty hard to do. It’s a thumb in the air. I think it could be this. What would your advice or lessons be around effective quota setting?

I think you start with: What are you trying to accomplish? What are you trying to do with your sales team? And be really honest about where your business is right now. Are you pulling? Is the market pulling you? Are you pulling the market? I think it starts with those things.

If where you’re ending up is, “Hey, we have an opportunity. We love what we’re doing, but we have to push it to the market, and we have to do that in a very proactive, strategic, outbound way, and we need X type of people to do that,” then index toward giving people more favorable quotas to entice great people to come in and do that kind of hard work, and you’re going to reap the benefits of it.

If you’re in a position where, again, you don’t know—the market’s moving so fast and there’s so much market pull, and you’re just trying to figure out how to keep up with it, and the job is more transactional at the time—then you probably want to build in some safety nets and focus more on the efficiency pendulum.

But I think it starts with: What are you trying to solve for?

18. When to Fire a Struggling Rep vs. Give Them More Time

How do you determine when enough is enough and when a rep’s not performing? Is it better to fire fast and make the decision, or is it actually better to give people more time?

I think it depends on where their challenges are. Again, I am generally pretty patient if you tell me someone’s working really hard, they’re improving, they have a growth mindset, and the tools are there; it’s just not quite coming together yet. I generally tend to be more patient because I’m always thinking about scale. I need hundreds of people, right? What’s the alternative to this person who’s busting their butt, getting better every day, has the desire to win, seems to have the aptitude, and it’s just taking time?

Like you said, if you hire 200 people, maybe 40 of them are good. It’s hard to find great people, and I think those characteristics are really fundamental to what great people look like.

If the problems are different than that—if they’re bad seeds, or they’re not working hard, or they’re complaining, those sorts of things—then I think you have to move much faster. I have a super-high bar and patience for the people who are doing all the right things but it’s not clicking yet, and I have a very low bar for the people who are not exhibiting the will, because I feel like that’s so much in our individual control.

You might not be able to control the quota, and you might not be able to control whether we gave you the right enablement or not, but you can control your attitude and how you show up every day. If that’s not there, I have no patience.

19. When and How to Verticalise a Sales Team

Final one for you, Shaunt, before we do a quick fire. I believe in vertical sales teams a lot. I think specialization and focus drive efficiency and outcomes. What would be your biggest advice to founders or sales leaders on when and how to verticalize sales teams effectively?

Yeah, I think focus and specialization—no question—as early as possible, in my opinion. Now, if we’re talking about verticalization, which by definition means peeling off specific industries and focusing people on a subset of types of customers, I think that is highly dependent on the product and the platform that you’re selling.

I can tell you that at Figma, to this day, we have not actually done any type of industry-based teams. But what we have done is think about sales motions and personas that we’re selling to, and create, in some cases through trial and error, some overlay teams.

We acquired a company called Weavy not that long ago, as you may know, and the way we’re going to market with that product right now is in a little bit more of an overlay motion. What we’re coming back to is: What are you asking one person to do, and is it too much?

At the point where you have to make the call—at the point where it’s too much for one person—you have to think about how you create more specialization. That might be segmentation, it might be verticalization, it might be overlay. You name it.

That’s what I always come back to: are we asking reps to do too much? Too much means understanding the product, the vision, the landscape, PLG, managing deals, and so on.

If we’re then asking them to master a new persona or a different type of motion, that might be too much. But I think it depends on each organization.

Dude, we’re going to do a quick fire. I’ll say a short statement and you give me your immediate thoughts. Does that sound okay?

Okay.

Which sales organization, other than your own, do you most respect, and why?

Datadog. I did work there, so I may have cheated a little bit, but they have been able to keep great people there for years and years and years. They really believe in promoting from within.

They’re another one of those few companies where they’ve mastered all the segments, from SDR to very, very strategic.

What is an outdated sales tactic that is no longer relevant?

Sending gifts?

Yeah. You don’t think that still plays?

I don’t. I’ve never understood it, to be honest with you. I think I have a pile of gifts sitting in some office in San Francisco that I don’t occupy right now.

I just don’t understand how a gift would help. It feels so transparent to me. It’s like, “I’m going to give you a bribe.” It just feels icky to me. I don’t get it. Could it work? Maybe. It doesn’t feel right to me.

Are remote sales teams dead?

Are they dead? No. Are they harder? I think so. It puts a lot more pressure on the system if it’s fully remote.

But are they dead? I don’t think so. I honestly think that if you go completely the other direction, you’re probably keeping yourself from being able to hire some really talented people. They’ve moved to cities where they’re not going to uproot their families now. They’re not going to go to New York or somewhere else.

I do think it puts more pressure on leadership, for sure. I don’t think it’s dead, and you’re missing out on some real talent.

What is your biggest regret, and why?

I try not to live with a lot of regrets. I will say that, going back to my early days at Figma, I had it in my head that I really wanted to come in and not be the guy who was just coming in hot and trying to change something I didn’t know anything about.

I probably went too much in the other direction in terms of spending too much time observing and trying to understand the culture that existed. That’s not to say we didn’t start implementing some things quickly, but I think I may have overdone that.

It’s not a regret, but looking back on it, I think it’s something I maybe would have approached slightly differently.

Final one. I like optimism. I’m a positive dude. What are you most excited for in the next 10 years? It can be anything.

For me, my mom has MS, so I’m very excited about drug discovery for rare diseases or maybe chronic illnesses. I think that’s super exciting.

Harry, we can take this offline, but I’ve had health issues surrounding me, and I feel very similarly. I’m always reading about the advances happening with AI and medicine. I’m very optimistic that’s one of the really good things that’s going to come out of this new wave of technology.

I’m looking forward to—I’ve got kids; they’re 9 and 7. I feel like I’ve got maybe 5 years where their mom and I are still the most important people in their lives. I really, really want to do my best to enjoy that and just be in it with them.

I’m interested in continuing to grow this team, and I’m really excited about the future and how the landscape is evolving and where we’re positioned in it. There are a lot of things I’m really excited about.

It’s fascinating. By the time your kids are 18, they’ve spent 92% of the time they will have with you.

I’ve seen that.

It’s appalling, isn’t it?

It burns me, and it’s really scary. I always feel like I’m trying to be so in it, and I think I am, but then I’m always asking myself if I could have done better. I think that just comes with the territory.

You know what? The older I get, the more I think we need to forgive our parents for that error. No one really knows what they’re doing.

Oh my gosh, 100%. My parents were trying to make ends meet, and to their credit, I look back at my childhood and I thought it was wonderful. There was plenty of drama mixed in, but they did the best that they could, and that’s all you can ask for.

Dude, thank you so much for being so brilliant. Thank you so much for putting up with my inquisitive questions and the rambling thoughts.

Dude, you’re amazing. The curiosity is incredible, and it’s a privilege to be on the show, to get to meet you, and to be among all of the other really brilliant people you’ve had the chance to speak to. Thank you.