Mar 21, 2026 · 1h 5m · news
This is why I don't believe in sales quotas | Figma CRO · 20VC with Harry Stebbings
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gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions
In this episode of 20VC, Figma's Chief Revenue Officer Sean Boscanian shares counter-intuitive sales philosophies, detailing how Figma scales its high-performing sales-led and PLG motions without relying on traditional customer success teams, SDRs, or conventional quota-setting methods.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Harry holds 15.9% of the talking time here. How this is scored →
Harry as informed peer 3.9 Guest teaching 4.6 Guest disagreement 1.5 Harry pushing back 3.9
speaking balance: gold is Harry, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 47:14 Quotas as lazy leadership
Sean takes a strongly contrarian position against traditional sales management by asserting that he doesn't care whether reps hit quota and that relying on quota creates lazy leadership.
Hardest push from Harry ▶ 49:41 Soft traits vs contract signingHarry forcefully rejects Sean's soft behavior framework, declaring that traits like curiosity and ambition are worthless if a seller fails to close contracts.
Biggest teaching moment ▶ 24:50 Enterprise PLG expansion complexitySean corrects Harry's characterization of PLG account expansion as easy order-taking, explaining the deep strategic skills required to navigate multi-stakeholder enterprise deals.
Harry holds his own ▶ 12:40 Seat-based pricing failure modesHarry demonstrates strong market expertise by explaining why seat-based pricing works for design tools but fails in labor-replacing categories like customer support.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Harry as informed peer | Guest teaching | Guest disagreement | Harry pushing back | Why |
|---|---|---|---|---|---|---|
| How Sean Boscanian Fell into Sales | 1 | 1 | 0 | 0 | Harry opens with an warm icebreaker about Sean's passion for sales. Sean recounts an anecdote about falling into sales while working at a cell phone kiosk in a mall. | |
| Stay Curious and Prescriptive | 5 | 5 | 2 | 6 | Harry pushes back on Sean's advice about curiosity, arguing that busy buyers do not want to spend time being qualified. Sean reframes the dynamic, arguing that enterprise sales requires pairing curiosity with prescriptive insights. | |
| Why Figma Doesn't Have a Traditional Customer Success (CS) Team | 5 | 5 | 2 | 4 | Harry asks how to structure CS and AE teams in a PLG expansion motion and poses a sharp question about selling platform value against superior point solutions. Sean explains why Figma views account expansion as a strategic hunting motion rather than traditional CS. | |
| Is Seat-Based Pricing Really Dead? | 7 | 3 | 1 | 7 | Harry challenges the idea that seat-based pricing remains viable across software by differentiating labor-replacement software from design tools. Sean acknowledges Harry's nuanced point about other business units. | |
| Pipeline Generation and the Rethinking of the SDR Role | 4 | 5 | 1 | 3 | Harry asks if the SDR role will survive the next two years. Sean reveals that Figma operates without traditional SDRs and requires AEs to generate their own pipeline. | |
| Defining Figma's Sales Segmentations | 2 | 6 | 0 | 2 | Harry asks how the Figma sales organization is structured given the lack of CS and SDRs. Sean gives an operational breakdown of Figma's three distinct GTM segments across self-serve, SMB PLG, and sales-led enterprise. | |
| Timing the Intercept for PLG Customers | 3 | 5 | 1 | 3 | Harry asks for specific advice on when a PLG founder should intercept self-serve customers. Sean explains the importance of early intervention and mapping customer account gaps. | |
| Sean's Philosophy on Sales Quotas and Rewards | 6 | 6 | 4 | 7 | Harry brings up 11 Labs' high quotas and asks how to drive rep urgency if quotas are dismissed. Sean declares that quotas are largely made up numbers and explains why Figma keeps lower enterprise quotas (3-4x OTE) to reward complex work. | |
| Deal-Closing Experience vs. Domain Expertise | 4 | 4 | 1 | 3 | Harry forces a choice between hiring deal-closing experience or domain expertise. Sean picks deal experience, and both agree that frequent job-hopping on resumes is a red flag. | |
| The Discovery and Demo Interview Exercise | 2 | 5 | 0 | 1 | Harry inquires about Figma's candidate assessment exercises. Sean details their take-home discovery/demo case study and flags candidate behavior during offer negotiations. | |
| Ramping sales talent: Fire Fast vs. Go Slow | 4 | 6 | 2 | 4 | Harry asks whether companies should fire underperforming reps quickly or hire slowly during rapid scaling. Sean argues for going slow, emphasizing that environment and coaching dictate rep success. | |
| Strategic Headcount Growth at Figma | 3 | 5 | 2 | 3 | Harry asks if Figma's leadership is pushing for headcount efficiency. Sean explains why Figma is actively expanding its sales headcount to deepen strategic account coverage. | |
| Tailored Onboarding and Field Engagement | 2 | 5 | 0 | 2 | Harry asks how founders should ramp new sellers. Sean outlines Figma's onboarding approach of getting strategic reps directly into account territories before formal classroom training. | |
| Rebuilding the Playbook and Managing Information Noise | 3 | 4 | 1 | 3 | Harry asks how Figma manages internal communication noise for reps. Sean candidly acknowledges that Figma has not solved information clutter across Slack and their CRM. | |
| Mitigating Rep Friction with Sales Tech and AI | 6 | 2 | 0 | 6 | Harry asks if Sean's focus on execution has led him to overlook modern AI sales tools and agent training. Sean agrees with the critique and admits the team needs to explore those solutions. | |
| Quotas as Lagging Indicators of Success | 5 | 6 | 5 | 7 | Sean shares his hot take that quota attainment doesn't matter and leads to lazy leadership. Harry cuts in to ask how leaders can possibly evaluate reps without quotas. | |
| Defining Core Sales Behaviors and Competencies | 6 | 6 | 4 | 8 | Harry pushes back against judging sellers on soft traits, arguing that curiosity means nothing if no contracts are signed. Sean defends his input-based competency evaluation model. | |
| Navigating "Lone Wolves" vs. "Bad Apples" | 5 | 5 | 2 | 6 | Harry roleplays as a top-producing lone wolf to test Sean's leadership tolerance. Sean distinguishes benign lone wolves from toxic bad apples that harm culture. | |
| Guidance on Strategic Quota Setting | 3 | 5 | 1 | 2 | Harry asks how to decide when an underperforming seller should be let go. Sean contrasts long patience for high-effort reps with zero tolerance for poor attitude. | |
| Specialization, Persona Focus, and Verticalization | 5 | 5 | 3 | 4 | Harry argues strongly for verticalizing sales teams early. Sean explains why Figma uses overlay motion specialization instead of industry verticalization, and rejects gift-giving as an effective sales tactic. | |
| Reflection on Professional Regrets and the Next 10 Years | 1 | 2 | 0 | 0 | Harry asks Sean about professional regrets and future outlook. Sean reflects on taking too long to make changes when joining Figma and shares excitement for AI in healthcare and raising his kids. |
Statements from this episode (32)
Figma operates without a traditional customer success team, says CRO Boscanian
“We don't actually have a traditional CS team.”
Figma operates without traditional sales development representatives, says CRO Boscanian
“We also don't have traditional SDRs.”
Figma CRO Sean Boscanian argues traditional software sales quotas are arbitrary
“My perspective is quotas are kind of made up.”
Figma sets average enterprise sales quotas at 3x to 4x OTE
“An average enterprise rep here might have three to four X their OTE for a quota, and we're happy with that.”
Enterprise sales success requires balancing curiosity with being prescriptive
“I believe like right now more than anything else, if you want to be great in, you know, 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…”
Most Figma customers originally onboarded via online credit card purchases
“Like most of our customers, even today, at some 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.”
Majority of Figma's sales team activity is outbound today, says Boscanian
“Oh yeah. A hundred percent. Not, not a hundred percent of our business up on, but a hundred percent in that the, what the sales team is doing at Figma is majority outbound today.”
Figma's net dollar retention rate recently increased from 131% to 136%
“We added five points on our net retention, pretty significant when I think went from 131% to 136%.”
Figma will monetize its AI features through a credit-based pricing model
“We're gonna start monetizing our AI usage through credits as well.”
Figma AEs must generate their own pipeline without relying on SDRs
“A's have to be responsible for their own PG, like full stop. That I think is, is 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, like the most important part of the job.”
Figma shifted its SDR team to manage small transactional renewals
“Recently we made a new shift, and we said even that we're gonna 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 th…”
Sales teams should intercept PLG customers early to drive upgrades
“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-…”
Most Figma sales reps operate a traditional enterprise sales motion
“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.”
Figma enterprise reps focus on account expansion over net-new logos
“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 done, we've had to do ruthless prioritization on like which accounts are we going to really go deep on. But once they get their accoun…”
Over-assigning sales quotas gives management a false sense of security
“I don't necessarily believe that 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 of a false, you know sense of comfort.”
Prioritize deal-closing experience over industry domain knowledge when hiring sales reps
“I, 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 with, to the person who's got, you know, the right willingness to learn and the curiosity, and obv…”
Figma CRO has a visceral negative reaction to jumpy sales resumes
“I have a usually a pretty visceral reaction to people who are super jumpy, you know, in terms of a resume.”
Figma requires sales candidates to complete practical discovery and demo exercises
“So we always make people do, you know, a challenge or an exercise at the end that requires 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.”
Demos test candidate perseverance while discovery reveals curiosity, says Boscanian
“And personally, I'm much more interested in how they do, frankly, on the discovery side of that, because I think, you know, 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…”
Candidates who pit competing offers against a company pose retention risks
“If at the end of a process, you know, 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. And if they're actively trying to pit you against a, …”
Figma's revenue organization is approaching 500 people, says CRO Boscanian
“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, et cetera, yeah.”
Figma supports 500,000 customers with roughly 300 quota-carrying sales reps
“You've got a half million customers you're trying to support with, I don't know, 300 quarter carrying reps, whatever the number is, like, you're pretty freaking efficient already.”
Figma assigns enterprise reps to accounts before formal product training
“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 acco…”
Figma is shifting sales onboarding back to in-person, classroom-style training
“We're also moving to classroom style. In person. And, you know, 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.”
Managing sales reps purely by quota creates lazy leadership, says Boscanian
“I just think it's too much of a lagging indicator. And I think it, 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 their number at the end of a month, quarter, or ye…”
Figma's sales team uses MEDDIC and a custom value selling methodology
“That's an the ability to actually manage your pipeline effectively you know, leveraging our medic framework. That's when you're doing discovery, we teach calm. We call it Figma value selling, but are you leveraging Our methodology, how you're, when you're doin…”
Management frequently sets sales quotas too high, admits Figma CRO
“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.”
Outbound sales teams should receive more favorable quotas to attract talent
“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 pe…”
Figma has never organized its sales force into industry vertical teams
“At Figma we to this day have not actually done any type of like industry based teams”
Figma CRO considers Datadog to have one of tech's best sales orgs
“Datadog. Well, 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'…”
Sending gifts to sales prospects is an outdated, ineffective tactic
“Sending gifts. Yeah. I've never, 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, I just don't understand how a gift wo…”
Refusing remote sales hires locks companies out of top talent
“Are they dead? No. Are they harder? I think so. I mean, it is, 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 …”