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Figma CRO considers Datadog to have one of tech's best sales orgs

Sean Boscanian · This is why I don't believe in sales quotas | Figma CRO · 20VC with Harry Stebbings · Mar 21, 2026 · at 1:00:03

Sean Boscanian, Chief Revenue Officer at Figma and former VP of Global Sales at Datadog, answers a quick-fire question on 20VC regarding which sales org outside Figma he respects most.

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“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've kind of mastered all the segments, SDR, to very, very strategic.”

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More from Sean Boscanian

Opinion
Figma CRO Sean Boscanian argues traditional software sales quotas are arbitrary
“My perspective is quotas are kind of made up.”
Sean Boscanian Mar 21, 2026 ▶ 22:13 This is why I don't believe in sales quotas | Figma CRO · 20VC with Harry Stebbings
Insight
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.”
Sean Boscanian Mar 21, 2026 ▶ 14:02 This is why I don't believe in sales quotas | Figma CRO · 20VC with Harry Stebbings
Insight
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…”
Sean Boscanian Mar 21, 2026 ▶ 48:18 This is why I don't believe in sales quotas | Figma CRO · 20VC with Harry Stebbings
Disclosure
Figma operates without a traditional customer success team, says CRO Boscanian
“We don't actually have a traditional CS team.”
Sean Boscanian Mar 21, 2026 ▶ 7:52 This is why I don't believe in sales quotas | Figma CRO · 20VC with Harry Stebbings
Disclosure
Figma operates without traditional sales development representatives, says CRO Boscanian
“We also don't have traditional SDRs.”
Sean Boscanian Mar 21, 2026 ▶ 13:34 This is why I don't believe in sales quotas | Figma CRO · 20VC with Harry Stebbings
Disclosure
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.”
Sean Boscanian Mar 21, 2026 ▶ 0:18 This is why I don't believe in sales quotas | Figma CRO · 20VC with Harry Stebbings
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