Sean Boscanian

10 statements across 1 episodes · 3 bullish · 2 bearish · 1 people on the record · first statement Mar 21, 2026 by Sean Boscanian · across every show →

On the record as a speaker too: Sean Boscanian's record, appearances and statements → this page counts the times other people say the name.

Everything said about Sean Boscanian, oldest first

Mar 21, 2026 negative
Insight
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.”
Sean Boscanian Mar 21, 2026 ▶ 23:32 This is why I don't believe in sales quotas | Figma CRO · 20VC with Harry Stebbings
Mar 21, 2026 negative
Opinion
Sending gifts to sales prospects is an outdated, ineffective tactic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…”
Sean Boscanian Mar 21, 2026 ▶ 1:00:29 This is why I don't believe in sales quotas | Figma CRO · 20VC with Harry Stebbings
Mar 21, 2026
Insight
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-…”
Sean Boscanian Mar 21, 2026 ▶ 18:43 This is why I don't believe in sales quotas | Figma CRO · 20VC with Harry Stebbings
Mar 21, 2026
Assertion Not checkable as stated
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.”
Sean Boscanian Mar 21, 2026 ▶ 19:28 This is why I don't believe in sales quotas | Figma CRO · 20VC with Harry Stebbings
Mar 21, 2026 positive
Insight
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 …”
Sean Boscanian Mar 21, 2026 ▶ 1:01:06 This is why I don't believe in sales quotas | Figma CRO · 20VC with Harry Stebbings
Mar 21, 2026
Insight
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…”
Sean Boscanian Mar 21, 2026 ▶ 3:46 This is why I don't believe in sales quotas | Figma CRO · 20VC with Harry Stebbings
Mar 21, 2026 positive
Opinion
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'…”
Sean Boscanian Mar 21, 2026 ▶ 1:00:03 This is why I don't believe in sales quotas | Figma CRO · 20VC with Harry Stebbings
Mar 21, 2026 positive
Insight
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…”
Sean Boscanian Mar 21, 2026 ▶ 55:28 This is why I don't believe in sales quotas | Figma CRO · 20VC with Harry Stebbings
Mar 21, 2026
Insight
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.”
Sean Boscanian Mar 21, 2026 ▶ 52:06 This is why I don't believe in sales quotas | Figma CRO · 20VC with Harry Stebbings
Mar 21, 2026
Insight
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…”
Sean Boscanian Mar 21, 2026 ▶ 27:07 This is why I don't believe in sales quotas | Figma CRO · 20VC with Harry Stebbings
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