# Figma CRO: Building Sales Machines on PLG Foundations

**Podcast:** The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch
**Published:** 2026-03-21

## Transcript

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 4x their OTE for a quota.
Focus and specialization as early as possible.
This is 20 Sales with me, Harry Stebbings.
Now, 20 Sales is the monthly show where we sit down with the best sales leaders to unpack how they hire, train, and retain the best sales talent.
Today, we have Sean Vosganian joining us in the hot seat.
Sean is the CRO, Chief Revenue Officer at Figma, where we discuss how to build a sales machine on top of a PLG Motion.
But before we dive into the show today, a quick shout out to a company I've been genuinely blown away by and have been tracking closely, ROX.
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So that means more meetings, higher conversion rates and faster revenue growth.
If you're an early stage startup, tired of duct taping sales tools together and looking to grow revenue faster, check out Monaco at monaco.com.
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You have now arrived at your destination.
Sean, it is so good to have you on the show, dude.
I said I'm so lucky in the way that, like, I get to interview the coolest people.
And, like, Figma is a product.
It's incredible.
The machine that you've built is awesome.
I'd just love to start on you and, like, the love of sales.
When did you know that you loved sales?
Was there, uh-huh, this is my career?
It happened kind of by accident when I was going to school, graduating high school, thinking about college.
I mean, there was obviously the sales profession, but it wasn't something you really studied.
I ended up going to school at BU.
I was studying advertising.
The summer after my freshman year, we had to get a summer job.
And I remembered just like the year before I got my very first cell phone.
So this is back.
you know, 2000, cell phones were becoming a thing.
You didn't have them when you were much younger than that.
And I remember when I got my phone, it was in a mall, it was in one of those kiosks.
And I remember asking the woman who worked there, I was like, hey, how did you get this job?
She's like, well, I'm a law student and this is a way to make extra money and you can do really well.
And I was like, I wonder if like I could do that.
So, you know, I went to the same.
kiosk in the mall, met this guy who was working there.
And I said, hey, how does one get a job like this?
I have no idea.
But I'm, you know, I'm home for the summer.
I'm looking for work.
He said, well, why don't you start by just like writing down some information here about yourself?
So he gave me this piece of paper.
I wrote down my name, my address, my phone number.
He's like, OK, great.
You start Tuesday.
I was like, what do you mean?
He's like, yeah.
cool, you're hired, man.
And I showed up Tuesday.
He handed me some pamphlets.
He was like, these are the planes 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.
And he left.
And I was like, oh my God.
And I started figuring it out.
Knowing all you know now, you can call up that boy with those cell phones and give one piece of advice on how to be successful in sales.
What piece of advice would you give?
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?
And what I mean by that is people are very...
cautious and hesitant with giving their time to anything.
It's more like, Sean, 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?
But if you're going to do qualification on me, I don't want to be qualified.
You should figure it out.
So I do think it's a skill.
And 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.
And that's an interesting balance, right?
Because 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?
And 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.
And I think that's the art of it is you have to be able to do both at the same time or else you're not going to be successful.
Can I ask with you in jumping, when you look at Pigma State, 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, this was what I, so I joined, I've been here about four and a half years and I started talking to Dylan five and a half years ago.
And at the time it was really early in the journey, but it was kind of unique in that.
Figma has been around since 2012 and really spent like six years building the product, studying customers, really trying to perfect it.
Really not something that I had heard happen very, very often.
And then once we started monetizing, this is like end of 2017, end of 2018, really took off.
And it took off very much in this, not even PLG, I would say self-service way.
Like most of our customers, even today, at some point, point they 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 and that happened really really fast and so when i joined four and a half years ago we were a hundred maybe fifty million dollar company but in terms of our penetration in the market we had Tons of customers, way more.
So I joined Datadog, my previous company, similar stage in terms of revenue, nowhere near the number of customers.
So in many ways, the job at Datadog in the early days was much clearer than it was at Figma.
In Figma, we'd 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 four and a half years ago was almost exclusively responding to existing customers that are on self-service plans.
And all we are doing is upgrading them to...
higher tiers of the product.
That was the motion.
You fast forward to today, it's very, very different than that.
We are global.
We have multiple segments, SMB, mid-market, enterprise, strategic.
And if you look at what most of our sales reps are doing, especially kind of mid-market plus, it's very sales-led.
The PLG motion of upgrading people to new tiers, expanding seats into the existing accounts, there's some of that, but so much of what's happening actually.
is what we were talking about before.
It's being prescriptive.
It's going into the customer with insights.
When you say it's sales led, do you mean it's outbound?
Oh yeah, 100%.
Not 100% of our business is outbound, but 100% in that what the sales team is doing at Figma is majority outbound today.
Now 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 figured out how to use us in a particular way.
But we, through curiosity, through understanding patterns from how other customers are using Figma, we are approaching them with...
proactive insights for how they should be and thinking about doing more with us.
Who is responsible for that?
Is that account execs?
Is that CS?
How do you structure responsibilities in the team when you have that?
We don't actually have a traditional CS team.
When I started...
We have a lot to figure out in terms of what is the motion.
And what we realize is 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 is that Figma could deliver to them.
If you look across our customer base, and this is even true today, you compare what an average customer is doing with Figma compared to what we think they should be doing with Figma, there is a pretty big gap and a pretty big discrepancy.
And so our job is how do we go and proactively educate the customer on the more that they can be doing?
And so 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.
That is a motion where in order to be successful doing it, you have to go in and you have to actually get, in some cases, 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?
We want the same people to use more.
Or is it we want more people to use the same product?
I know it's both.
But if there was one more.
Honestly, it is both.
I think for the most part, and by the way, this has evolved too, as we've gone from single product to multi-product.
I would say right now, it's probably a little bit more on the using new products side.
And 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 which go multi-products that i'm invested in and the reps honestly know that verticalized solutions are better at point function 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 mean i think frankly like the best sellers are not the ones that are focused on this feature is better than this other you know companies 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 to those things that they're trying to accomplish.
And there's a storytelling aspect.
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 is the customer really going to get the most value from what you have to offer compared to the competitor?
And 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 I think if it's the platform, then that's the narrative that you want to get the customer to believe in.
When we think about that platform expansion and product expansion in terms of usage, everyone is saying that seat-based pricing is dead.
Do you agree?
If so, what comes next?
I think it is hard to predict the future on this one, honestly.
But if you look at our own business, I mean, we had our earnings call a couple of weeks ago.
We added five points on our net retention.
Pretty significant.
I think it went from 131% to 136%.
Obviously, today, we're in a pretty much exclusively seed-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's just more and more builders, I think, coming into software as it exists.
So 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.
And 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 or 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, I mean, like it makes that makes sense.
I'm just not as knowledgeable about what's happening in those, you know, 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.
Totally get that.
It's an interesting kind of pushback on the traditional narrative.
Another aspect that I see more and more is like the destruction of the role of the SDR.
Does the role of the SDR survive in two years time?
Do AEs just be completely responsible for pipeline generation PG?
How do you think about that one?
Well, I'm kind of smiling because we also don't have traditional SDRs.
We really tried to be first principled with how we built.
They go to market at Figma.
And by the way, this is coming from someone who had, you know, by the time I left my previous company, maybe 200 person SDR team, a pretty traditional one.
So here's what I'll say.
First is A's have to be responsible for their own PG, like full stop.
That is consistently true anywhere I've been.
And I firmly believe in it.
I think with SDRs, I've always tried to be really thoughtful about.
Where is the SDR actually adding clear incremental value in a business where you expect AEs to PG as well?
And honestly, anywhere I've been, it's always been a little bit challenging to really isolate.
Okay, what did the SDR do versus 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 kind of struggled with it.
At Figma, there's this other unique aspect, which is, again, our product.
The problem is not acquiring new customers, right?
We have a lot.
And so much of our focus is how do 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 go expand into specific personas and do things like that.
But actually recently we made a new shift and we said even that we're going to kind of take.
the focus away from.
And we're using them now in a more pointed way on existing customers and managing small, you know, 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 kind of tinkering with like, what's the best way to deploy that resource to get value?
And then of course, they're a talent pipeline as well.
There are future reps.
So we have no SDRs and we have no CS.
So just so I understand, the sales team is structured with AEs.
What else do we have in there?
When I started, it was basically we had AEs and AMs.
We had two segments, mid-market and enterprise.
And if you looked at what mid-market and enterprise was doing back then, it was effectively the same thing.
They were doing PLG.
They were upgrading people.
It was a single product company.
And then AMs were...
effectively doing CS type of work.
They were driving seat expansion, but really like they were doing support.
They were trying to be really responsive to the customer.
It was necessary for the point of the business we were in.
When we looked at it, we said, okay, what do we need in the future?
And one of the things I believe in the most is you need to have focus.
Like the best sales teams are the ones that are like really, really focused and specialized.
So 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 we said, where are there places where we can create focus?
And the first thing we realized is like, let's isolate this PLG motion.
So when we looked at it at the time, where is the PLG, that upgrade?
When I say PLG, so by the way, maybe to define this for everyone, I think we kind of have three distinct businesses at Figma.
One is self-serve.
That is people go on the website, they put in a credit card, they buy what they think they need.
And you can buy or lower to your plans directly through the website.
And 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 what we call our SMB segment.
Those are reps that are covering zero to 500 employee businesses.
And then we have our sales lead, which I'd consider mid-market enterprise and strat.
And those are just basically smaller book sizes, smaller companies.
So that's the way we're kind of 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, it was new startups that were coming into the ecosystem.
They were buying licenses themselves.
And then we try to be really sophisticated around when is the right time for us to proactively reach out to them based on product signals, maturity that we see happening to then have a conversation around, OK, you need to move up tiers.
I'm a founder with a PLG motion.
What is the one piece of advice you would give to me on the right time to intercept?
Could be duration, could be usage, could be seed expansion.
What is that sign?
I don't think it ever hurts to do it a little earlier than a little later, because I think what we do still find is we think it's the right time based on our formulas.
You still have to convince someone that that's the case.
And that might take a couple of go-arounds.
Our SMB team, they'll often lose a deal, right, as in an upgrade transaction, and then they'll win it.
a couple of months later.
And that's very typical.
It was typical of my last company as well.
But the what I think is dependent on so many factors around how people are using a product, which features you're gating, how they're interacting with it.
I don't know if there's like one specific answer to that.
When your business is basically expansions and upgrades, do you have pipeline reviews in the same way that it...
Oh yeah.
So by the way, just to finish, what we did is we said SMB, that's the PLG motion.
Everything else is sales led.
Everything else we do, mid-market enterprise strat, which is the majority of our team and the reps that we have, it's running like a very...
traditional SaaS sales business.
Again, what's unique is they're PGing primarily into what you would consider to be a customer.
We almost don't think of it that way.
The job of a sales rep, they get their book of accounts, right?
And every year we've created more focus around them.
And we've had to do ruthless prioritization on like, which accounts are we 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 is the best in class deployment of Figma look like based on your understanding of this type of business?
Where are they today?
And 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, how to actually go 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% they do PG.
They create opportunities.
We do pipeline reviews constantly.
We do forecast calls every week where we're digging into it.
And nothing super unique in terms of how we run that part of the business, except for the fact that it's not traditional net new that a lot of other companies would use as a definition.
What's your single biggest advice for how to create champions on steroids within a customer base?
There's a few things.
First is 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, OK, I'm all in.
It's not just I love your product.
Of course, like the Figma community is incredible, but you want to build an enterprise champion, educate them, teach them something that 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.
When we think about kind of teaching them and converting them, I think sales comp is a very hard thing to get right.
We've had the CRO from 11 Labs on the show.
They have a 20x quota.
Is that a new world of PLG?
Is that 11 Labs specific?
And how do you think about the right quota setting?
I've got controversial, I would say, opinions on quotas in general.
My perspective is quotas are kind of made up.
What I mean is, I think there's this kind of prevailing wisdom with...
quotas that I've seen, especially when you're going into planning and you're trying to map out your year, where you kind of go, okay, how much ARR do I need to generate?
How many people do I have?
How much quota do I need to then dish out to feel like I've got enough coverage where if we're trying to add 500 million next year, if I've got 600 million of quota out there, that means even if people end up at 80% attainment, I'm good.
And 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 it's more about...
philosophy that you're trying to implement around what is the work that needs to be done and how much reward do you want to dish out for that work that needs to be done?
I think it generally comes back to that.
And so I don't have a singular philosophy.
Can I tell you, if you don't have quota or don't believe in quota, how do you think about setting urgency, setting incentives?
I believe in quotas.
We have quotas.
What I'm saying is I don't necessarily believe you completely de-risk your year by making sure that you've dished out enough quota to cover your target.
I think that's a bit of like a false sense of comfort.
What I believe is that with quotas, you want to try to determine what are you trying to accomplish.
And the way I would think about it is I don't think there's like a single answer.
And I think even at Figma, we've evolved, right?
In the early days of Figma, which may be similar to what's happening at Eleven Labs right now, it was, you know, the job was...
primarily take this product, make your customer really happy, know the product really, really well, support them, and then viral expansion would happen.
And frankly, if you think about the job to be done, there is a pretty wide population of people that could likely do it.
If they come in and they care about learning and the product, et cetera, that's one thing.
And so if you have that business, you have to think about what is the reward.
for that.
What is the population of people that you can do that job?
Dude, is that job not quite easy?
You're essentially an order taker.
When people are pulling the product out of your hands and desperate to use it, kind of easy, no?
I mean, I think there's things about it that are hard.
I don't want to say it's easy, but I think the way I think about it more is like how many people out there could probably do it if we brought them in, trained them, and they had the right personality, they had the willingness to learn.
I think about it as you don't need to have 20 years of sales experience to figure out how to do that, even if there's things about it that are challenging.
I don't want to diminish what the job is.
But I think in that type of situation, right, you're probably focused more on driving efficiency in the business.
Where we are right now in that SLG motion and- particular, which is again, mid-market enterprise strat.
What we're asking people to do, the stuff you just heard me get so warm and fuzzy about when I heard customers talk about in terms of bringing insights and building champions, that is strategic work.
You need people who can really understand how businesses operate, who really understand not only the product, but the landscape that we're operating in, who are able to PG and build these relationships, bring these insights, manage complex multi-stakeholder deals.
That is hard work.
And it's very, very strategic work.
11 Labs is doing is probably perfect for them.
I'm in the opposite side of the spectrum right now where it's like, I want people to feel like Figma is a place where you can come in, you can do this hard strategic work that's really driving value for your customers, and then you can be outwardly rewarded by it.
And so our, you know, an average enterprise rep here might have three to four X their OTE for a quota.
And we're happy with that.
You can have someone who 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 two options to choose from, I would take the person with the experience doing the deal.
Because I think the industry experience, you can teach to the person who's got, you know, the right willingness to learn and the curiosity.
And obviously, you need to make sure you have that in a person and you test for it.
I'm kind of making a bit of an assumption that with those two choices, the person who's done the really big deal hasn't just got a bluebird, right?
That they've managed multi-stakeholder, long sales cycles, have to build a lot of champions, have to get to EBs.
They're likely leveraging something like Calm and they're using Medic and they're familiar with these concepts.
There's a lot more confidence that I think that needs to be built over time for people to be really good at that.
And I think generally speaking, smart people can learn industries and landscapes in a shorter period of time.
So if those are my two...
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 looked for in sales reps changed over time i don't know that it's changed that much to be honest with you i mean the first thing there is i think what you see on paper and i think that matters and i think increasingly i've become more opinionated on what i'm looking for there and what i'm not i i have to admit some people don't agree with this i have a usually a pretty visceral reaction to people who are super jumpy, you know, in terms of a resume.
And when we say super jumpy, I know it sounds awful, but this is like one year, one year, one year.
Exactly.
Like 12 months here, 18 months here, 12 months there.
There's so many reasons why people would encourage me to have more of an open mind for it.
And I get all of that.
But generally speaking, when you're doing this at scale.
I don't know.
I think it's total bullshit.
If you've done it four times.
Right.
It's saying something.
Yeah.
Once it could be culture, it could be family, it could be whatever.
But four times?
Yeah.
So, I mean, look, then 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, that they are 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.
I mean, you know, I think like what Dan would tell you, and I think he mentioned it when he spoke to you, is like he really wants to get like the full history of the person kind of going back to school days and how they made their decisions.
I will do that from time to time.
I don't always do it.
Frankly, the thing that...
tells me the most on that front is the resume, you know, looking at the places they were and having a sense of like the arcs of those places when they were there.
Is this someone who was just chasing something that was easy or were they really actually sticking with something and making success out of something that wasn't successful?
I think that's a big part of it.
You know, even you can create a process that forces perseverance through it in terms of an interview process.
So we always make people do, you know, challenge or an exercise at the end that requires some some heavy lifting in terms of like learning a bit about our business but also showing off your you know basic sales skills run discovery so i think that's a way to do it too but it is hard it's hard what is what is the challenge your exercise is the take-home assignment it's a take-home assignment we've evolved it over time but it's kind of a combination of disco demo you know it's basically like we want to give people a use case you know a case study you're gonna go pitch to this customer here is 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, frankly, on the discovery side of that, because I think it's probably a little bit unfair to expect someone to be doing this amazing demo of your product with just a few days of playing around with it.
But I do think, actually, the product piece we've kept in there, because it does show 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.
And then the way they approach the discovery part, I think, tells a lot around their ability to actually be curious and do all of those things.
Okay, so we're really impressed with this candidate, me and you.
And we're thinking, great, we should hire them.
And we move to 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 backchannel.
I think that's a little bit outside of the question you're asking, but I think getting signals outside of the process in some ways, I think are like the most valuable insights that you can get on someone.
I think on the offer stage itself, look, you have some people who are going to naturally negotiate.
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's not negotiating is not negotiating at the end because the hiring manager, the recruiter have done a good job of positioning ourselves and our offer in a way that makes them really just happy to jump in and take it.
But the biggest thing I'm looking for at that point is someone's got to be all in.
Like they have to be really excited to come on board.
And look, I understand people have choice and I fully respect going through.
process with multiple companies.
But if at the end of a process with Figma, spending a couple of weeks doing all this work, if you're not like, all right, I'm in, I want to do this, it tends to be a little bit of a yellow flag for me.
actively trying to pit you against another company, I just get nervous because we've seen some people who we've hired like that.
And then, you know, as soon as things are tough or, you know, they didn't have the initial success they expected or that other company that maybe they didn't tell you, but they're actually more excited about came back with a better offer or a different offer, they leave.
And so do all the investigation you want to do during the process.
But then by the end, like both sides should feel like they're all in on this candidate.
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 fast and be quick with decisions?
Or is it better to go slow and miss hiring plan?
I think it's between those two choices, I would prefer to go slow and risk potentially missing the hiring plan.
Because if you make that wrong hire, it doesn't matter how fast you move, you've cost yourself time, in my opinion.
And look, it's a balance.
But look, at the end of the day, if someone comes to me and they're like, hey, I know I've been sitting on this open headcount for three months.
I have someone, I'm not that excited about them.
I think they could maybe grow into like a solid B player.
I'm never going to say hire that person.
I'm just not going to do it.
it, even if it risks the hiring plan.
I met a founder yesterday and they were increasing their sales team by 200 reps in the next 12 months.
And I was just like, honestly, how many do you think will be good?
And he was like, probably 20.
Yeah, I think it's slightly different than resigning yourself to hiring that BRC player.
But I think it's facing the reality that you can build the best process, you can have the best instinct.
And I still come back to the little...
joke I made earlier, which is like really figuring out if someone's great in an 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 actually, it really starts where you have to figure out, do you have someone who's going to be able to grow and be successful?
Or did you make a wrong hire?
And do you have to do something about it?
And I also think that it's not always as simple as right hire, wrong hire.
I actually think Most people have the potential in them.
Some don't, and you might make some mishires, right?
But a lot of people, I think, have potential.
And there's so many factors that actually contribute to are they going to be successful or not?
How great is their leader?
How great is the enablement?
How much of a chance did you actually give them?
I've got people who've gone on plan.
The person I'm thinking of actually from my last company went on a performance plan and...
was really struggling.
But we kept looking at like all of their inputs.
There were so many great things that they were doing.
And we said, let's focus on just coaching around the areas that are gaps and came off of it.
I'm long gone.
That person is still there.
Multiple promotions, one of their most successful reps.
So I actually think that it's not as simple as did you hire the right person, the wrong person, but did you put them in an environment where they can succeed?
And are you actually holding them accountable to the right things?
Can I ask you, how big is your sales team today?
We're probably pushing 500 in my whole org.
That's not just sales quota carriers, but if you include some of the supporting resources, etc.
Will sales teams be larger or smaller in the future?
Is DLM pushing you to be more efficient?
No, I think we're kind of going the opposite.
Truly, we talked a lot about efficiency in our early days.
And I think now, like how much more efficient can you get, right?
You've got a half million customers you're trying to support with, I don't know, 300 quarterly carrying reps, whatever the number is, like you're pretty freaking efficient already.
So I think this might be like a unique Figma thing that for us, I'm pushing and Dylan is on board with.
more headcount in sales to do more of the strategic work with customers that we really are seeing great results from.
I think we're going to continue investing in sales headcount.
Going back to the hiring process, when you've made a mishire, what did you not see that you wish you'd seen?
Like for me, one is like when I'm constantly pushed by the candidate on role and they want an increased title and I always push it to the back.
I'm like, well, they're brilliant.
So of course they want to be a X.
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.
And look, we're all in sales.
Like there's little mercenary in all of us.
And I get it that in some ways we're in sales.
This is kind of what the profession calls for.
But it's some of my best people over the years where money wasn't the first thing that they were thinking about.
Career growth, learning and development, different.
That's very, very different to me.
But I think the best people actually kind of know that if you're prioritizing those things, the money comes.
And I think, in fact, some of the people who've been the best earners that I've been around in past 10 years, they haven't been the ones that were focused on, I got to maximize my W-2.
And in fact, I've seen people who, when they're chasing that, It goes the other direction.
So that probably is my answer.
I think there needs to be a passion for growth, for career acceleration, for learning development, for collaboration, for people who want to just get better.
The growth mindset, I think, is the biggest thing.
And so if people are too focused on things that aren't suggestive of growth and is more focused on the individual and this point in time thing, that's a yellow flag for me.
So we make this hire and it's time for them to ramp.
And I'm a founder.
You're an angel investor in my company.
I'm sorry.
You've just probably burnt your money.
But go with me on this journey.
How do I ramp new reps effectively?
Take me to an enterprise rep and give me their onboarding.
I think for an enterprise rep, one of the things we want to do is kind of as quickly as possible, even before we teach them all the product stuff and the sales skills, which hopefully they're bringing some with them, we kind of want to get them into their account and their territory.
First thing, kind of throw them into the fire on, you know, you've got one or two 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 that was working on it or the manager or director is talking to them.
Let's get you engaged and let's just get you having building relationships and learning that business.
And then I would say after a couple of weeks, like they've, you know, they've gone through, they've got their laptop.
They understand what account they have.
They've maybe been on a few calls where they've listened in.
Now we want to get them into like a proper onboarding.
And 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 strat rep in this example, they better understand the.
landscape really well so they knew they need to know the product obviously in 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 like here's a file of facts go learn it this is to be honest with you we're rebuilding this right now What we're talking about right now, we're rolling out.
We actually did this week.
We're doing our soft launch of the new version of it.
But that is what we are striving toward.
It's very much like we're also moving to classroom style in person.
And in the COVID days, we kind of got away from that.
But we're going back to classroom style.
We're going back to in person.
We're bringing in the thought leaders across the organization, across these different pillars.
And absolutely, we're going to educate them on this is what's happening in the tech ecosystem.
These are the different players that you.
Your customers are going to be thinking about potentially using.
Here's our positioning in that conversation.
Here is what our best customers are doing.
Here are the things you need to understand about the product.
And then, of course.
Here is our sales process.
They need to understand our sales process beginning to end, all of the resources that are available to them along the way, all of the things that we're going to do to help them, pipeline reviews, forecast calls, the operating rhythm that we built here.
So it's taking them through all of those things.
Again, once they've got a little bit of footing underneath them, and then it's ongoing enablement.
It's something new happened in the market.
How do we make sure the whole team is educated on it?
So we have recurring enablement stand-ups that we do where it's like, 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 you 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.
I think if you talk to our reps, it's one of the things I'd complain about.
If I'm being completely honest, we have improvement to do there because we kind of use it all.
We have our sales enablement platform.
Then, of course, we have Slack and our Slack is as noisy as a lot of the other companies that get to our scale.
We are doing things.
in person.
We are doing things on Zoom.
We have content everywhere.
And again, we have so many customer stories that they end up in multiple systems.
And of course, we have, I didn't even mention our CRM, that 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 and we're going to have everything go to one place and have a singular approach.
So I'm being honest, we don't have that solved yet.
How do you think about pushing the boundaries of sales technology adoption within the team?
Like, again, Jason's one of my best buddies.
He is so versed on qualified, momentum, artisan, all the different providers.
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 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?
Getting better ourselves, the conversations we're having with our customers.
So to your point, just in these last few weeks and months, I've been much more...
passionate about where can we invest more in either agentic solutions or exciting tech that can make some of this stuff easier.
It just comes back to, I want to make the job of our reps easier.
It's very clear where they're really happy and where there's frustrations.
I think every company you're going to have both.
And I think the frustrations on our side right now would be from the fact that there's a lot on their plates.
And I think if we can leverage some of these new technologies to remove some of the friction on the duplication of data entry and those types of things, I think it's not a hard thing to do that will make a meaningful impact.
I don't mean this badly.
Do you think you and the team are equipped to train agents in the way that they're needed 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 that are that versed in how to train the next generation of sales agents.
Yeah, I don't know.
I don't know that we are.
We will need to explore and figure out if we're capable.
And if not, we're going to have to, you know, 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.
Because 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 I kind of don't care if you as a rep hit your quota or not.
And what I mean by that is, first and foremost, similar to the discussion we're having before, I've been in situations consistently where we're doing our best to set a quota based on that philosophy, right?
I just shared our philosophy right now is to try to do aggressive ones, 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.
And that could be in either direction, right?
You set them too high.
Oftentimes you set them too low, whatever, compared to what you expected.
I think of quota as both something that's more systemic than something that is entirely on the individual.
Also, the other reasons for this is I just think it's too much of a lagging indicator.
And I think what my fear is it creates lazy leadership.
If we're performance managing based on the idea that someone got to their number or didn't get to the number at the end.
of a month, quarter, or year.
If you're a strat rep, you know, we don't really know how to judge you until the year is over, right?
If you have one account and you're building towards this big renewal at the end of the year, from a quarter perspective...
So 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.
So we have written out, and by the way, it's probably, if I'm being honest, maybe too detailed, but one of the first things that we did is we wrote out a performance framework and we said, by the way, quota's part of it, right?
There's a results category and I'm not dismissing quota entirely, but there's a results bucket and that's just one bucket.
And that is not just results from a quota perspective, it's PG.
it's you know all the the success metrics that we are tracking and then behaviors and we documented what does that mean and then competencies we documented all of the competencies that we actually care about can we just dig in what what is behaviors and competencies though because like if you have like curious and ambitious dude i can be curious and ambitious and sign no contracts yeah well i mean i think the behaviors one is is like probably a little bit simpler and straightforward it's 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, you know, negative constantly in the office and impacting the people around you?
I mean, there's like some basic things there.
Competencies, which I think are like the most critical.
Those are, hey, 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?
So that's the ability to do PG effectively.
That's the ability to do discovery effectively when you're talking to a customer.
The ability to actually manage.
your pipeline effectively, leveraging our medic 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.
And then back to just quickly the point around the hot take on quota, where I come back to is if someone says, hey, this person is not doing well, okay?
The first thing I'll ask is why?
And If they say, well, they didn't hit their quota, I'll immediately go, OK, well, let's talk about why they didn't.
And let's get into those competencies and let's get into those behaviors.
And if someone says, well, actually, this person is like totally busting their butt and they're grinding.
They've got amazing work ethic.
They've got a great attitude.
Like every day they're trying to get a little bit better.
And oh, by the way, their PG is really good.
It's just taking some time.
It's not translating.
When I listen to their calls.
They're executing calls really, really well.
And pipeline is being developed.
It's 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?
I get you.
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.
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?
And that happens.
It truly does.
And like, I agree with you, Harry, but we're trying to manage things at scale.
And what I don't want is to create a culture of lazy leadership.
I want leaders to be in the details.
I want leaders to not be talking by, well, I 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.
Like they're not working hard.
They're not capable of translating our enablement into conversation because that tells me the leader is in the boat with the rep.
They're not lagging indicators.
They're more real time.
I'm a lone wolf, but I make a lot of money.
And I close.
And I'm not bad for the culture, but I'm not collaborative and I'm not a team player.
You got a problem with me?
I think that there's a place for that, honestly.
And I know some great reps who you would probably define that way.
And actually, when you talk to them about it.
They don't even want it.
They're not.
It's not like they're proud of being a lone wolf.
It's just that this is how they're wired.
And, you know, like the job means something different for everyone.
So I don't really have a problem with it.
And I think I've actually seen people who are categorized that way where once you talk to them and you say, hey, buddy, like you're great.
But you know that like some people are defining you as a lone wolf.
Is that how you want to be known?
And they go, oh, shit.
No, I don't even know.
That's what people thought of me.
Thank you for the coaching.
And there's others who they're like, 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 like do my thing, make money and be successful.
And I think that's also perfectly OK, as long as it's not.
negatively impacting others.
That's one thing that I've really learned.
I've 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.
And we've seen them, we've had those experiences, multiple companies I've been at.
You can never move fast enough is my opinion.
I will say sometimes I don't know that they know.
Even in those situations, starting with giving feedback and coaching, I think 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.
So I still feel like you give the feedback, you give the coaching, but then it's still persisting.
You have to make a move.
We were kind of aligned, actually, in what we were saying around quota.
And you said, well, sometimes you've just set the wrong quota.
If you're advising another sales leader or me, a founder of an early stage company around how to set quotas effectively, pretty hard to do.
Thumb in the air.
I think it could be this.
What would your advice or lessons be around effective quota setting?
I think it's start with what are you trying to accomplish in what you're trying to do with your sales team?
And be really honest about where your business is right now.
And is the market pulling you?
Are you pulling the market?
I think it starts with those things.
And 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 towards 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 the market's moving, 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 its 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?
How do you determine when enough is enough and when the 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.
And again, I am generally pretty patient.
If you tell me someone's working really hard and they're improving and 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, again, I'm always thinking about at scale.
I need hundreds of people, right?
Like, what is the alternative to this person who's busting their butt and getting better every day and has a desire to win and seems to have, you know, the aptitude and it's just taking time?
You know, like you said, if you hire 200 people, maybe 40 of them are good.
Like, it's hard to find great people.
And I think those.
characteristics are really fundamental in what great people look like.
If the problems are different than that, if they're, like we talked about, they're bad seeds or they're not working hard, you know, they're complaining, those types of things, then I think you have to move much faster.
I have like super high bar in patience for the people that 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 that's just so, I feel like it's so in our individual control.
You might not be able to control the quota.
You might not be able to control, did we give you the right enablement or not?
But you can control your attitude and how you show up every day.
And if that is not there, I have no patience.
Final one for you, dude, before we do a quick fire.
I believe in verticalize sales teams a lot.
I think specialization and focus drives efficiency and outcomes.
What would be your biggest advice to founders or sales leaders on when and how to verticalize sales teams effectively?
I think focus and specialization, no question, as early as possible, in my opinion.
Now, if we're talking about verticalization, that like by definition, peeling off specific industries and focusing people in a subset of types of customers, I think that is...
Again, highly dependent on the product, the platform that you're selling.
So I can tell you at Figma, we to this day have not actually done any type of like industry-based teams.
But what we have done is we thought about sales motions, personas that we're selling to and creating, you know, in some cases it's been trial and error, but some overlay teams.
You may know we acquired a company called Weavey not that long ago and the way we're going to market with that.
product right now is is in a little bit more of like an overlay motion and what we're coming back to is like what are you asking one person to do and is it too much you have to just make the call at the point where it's too much for one person you have to think about how do you create more specialization?
And that might be segmentation, it might be verticalization, it might be overlay, you name it.
But that's where I always come back to is like, are we asking reps to do too much?
And too much means understand the product, the vision, the landscape, PG, manage deals, et cetera.
You know, one of the equations will be if we're then asking them to go 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 say a short statement.
You give me your immediate thoughts.
Does that sound OK?
OK.
Which sales org, other than your own, do you most respect and why?
Datadog.
I mean, I did work there, so I maybe 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.
And they're another one of those few companies where they've kind of mastered all the segments, SDR, to very, very strategic.
What is an outdated sales tactic no longer is relevant?
Sending gifts.
Sending gifts.
Yeah.
You don't think that still plays?
I mean, I've never understood it, to be honest with you.
I think I have like a pile of gifts that are sitting in some office in San Francisco that I don't occupy right now for me.
But like, it just feels so transparent to me.
It's called a bribe.
Yeah, like I don't, it just feels like you to me.
I don't get it.
Could it work?
Maybe.
Doesn't feel right to me.
Are remote sales teams dead?
Are they dead?
No.
Are they harder?
I think so.
It just puts a lot more pressure on the system I think if it's fully remote.
But are they dead?
I don't think so.
I honestly think like if you go completely the other direction, I think you're probably keeping yourself from being able to hire some really talented people that are, you know, they've moved to cities where they're not going to have families now.
They're not going to go to New York.
They're not going to go somewhere else.
Like, so I do think it puts more pressure on leadership for sure.
I don't think it's dead or you're missing out on some real talent.
What's your biggest regret and why that?
I try to not live with a lot of regrets.
I will say, Going back to my early days at Figma, I feel like I had it in my head that I really wanted to come in and not be the guy who's just coming in hot, trying to change something I didn't know anything about.
And so I probably went maybe too much the other direction in terms of too much time observing, trying to understand the culture that existed.
And that's not to say we didn't start implementing some things quickly, but I think...
I maybe overdid that.
It's not a regret, but I think looking back on it, I think it's something that 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?
Personally or in...
It can be anything.
So like for me, mom's got MS.
I'm very excited about drug discovery for kind of rare diseases or kind of maybe chronic illnesses.
I think that's super exciting.
Well, we could take this offline, but I've had health things surrounding me and I...
feel very similarly.
I'm always, you know, I don't know if it's real or fake, but I'm always reading stuff about the advances that are happening with AI medicine.
I'm very optimistic that that's one of the really good things that's going to come out of this new wave of technology.
So I've got kids, they're nine and seven.
I feel like I've got maybe five years.
where I'm still and their mom are still like 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.
So that I'm interested in obviously like continuing to grow this team.
And I'm really excited about the future and just how the landscape is evolving and where we're positioned in it.
So there's 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.
I know.
I've seen that.
It's appalling, isn't it?
It scares me, and it's really scary.
I'm always trying to be so in it, and I think I am, but then I'm always asking myself if I could have done better, and 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, Aris.
Oh, my gosh.
No one really knows what they're doing.
Oh, my gosh.
100%.
100%.
And my parents, you know, were trying to make ends meet.
And to their credit, I look back at my childhood and I thought it was wonderful, you know.
And 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 meandering thoughts.
Dude, you're amazing.
The curiosity is incredible and just a privilege to be on the show, to get to meet you, to be amongst all of the other really brilliant people that you've had the chance to speak to.
So thank you.
But before we leave you today, a quick shout out to a company I've been genuinely blown away by and have been tracking closely, ROX.
I've been watching this team closely and the speed they're operating at and the level of applied AI talent they've assembled, it's honestly remarkable.
ROX is pioneering revenue agents for the global 2000, plugged into your data warehouse and CRM and delivering board level ROI in just 90 days.
These sales and revenue agents handle the end-to-end sales process for large enterprises from research, prep to deal risk outreach and opportunity management so sellers spend more time with customers and less time in tools this isn't another productivity app christ we've all had enough of those rocks gives reps a single interface on top of their gtm stack powered by a knowledge graph across your internal and external data so if you want to boost ae productivity increase revenue per rep and consolidate your stack try rocks at rocks.com sign up And speaking of great companies, we have to talk about Monaco.
For years, I've watched some of the best founders and early go-to-market teams struggle with sales.
Too many CRMs, too many point solutions, too much manual work.
Well, that changes with Monaco.
Monaco replaces your legacy CRM and fragmented sales stack with a single AI native platform.
Monaco's agents automatically build and score your entire TAM, layer in real-time signals, create and run outbound sequences, schedule calls, and record and transcribe meetings.
Your pipeline practically manages itself.
Monaco creates reminders, drafts, follow-up emails for you and keeps deals moving forward.
So that means more meetings, higher conversion rates and faster revenue growth.
If you're an early stage startup, tired of duct taping sales tools together and looking to grow revenue faster, check out Monaco at monaco.com.
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