Calendly

7 statements across 1 episodes · 1 bullish · 0 bearish · 1 people on the record · first statement Sep 1, 2022 by Annie Pearl · said 46 times in 15 episodes since 2015 · across every show →

Mentions by year

brought up most by Harry Stebbings (17), Annie Pearl (10), Joost de Valk (5), Jason Lemkin (5), Marvin Liao (3), Kieran Flanagan (3), Rory O'Driscoll (1), Edwin Chen (1)

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2026 2 mentions in 2 episodes 1 per episode
2025 1 mention in 1 episode
2024 4 mentions in 2 episodes 2 per episode
2023 10 mentions in 3 episodes 3 per episode
2022 25 mentions in 5 episodes 5 per episode
2020 1 mention in 1 episode
2015 3 mentions in 1 episode

every mention, scene by scene, with the transcript →

Everything said about Calendly, oldest first

Sep 1, 2022
Insight
Pearl: Pure PLG growth naturally slows at hundreds of millions ARR
“The sort of PLG motion, which, you know, in a lot of ways is really just a self-service motion, can get you into the several hundreds of millions of dollars in revenue scale. But typically the ACV is really low, or the account value of those users, and so just…”
Annie Pearl Sep 1, 2022 ▶ 8:57 Calendly CPO Annie Pearl: Hiring Advice for Product; Calendly's Second Product | 20VC #921 · 20VC with Harry Stebbings
Sep 1, 2022
Assertion Not checkable as stated
Pearl: 80% of horizontal software functionality satisfies vertical departmental needs
“So when you think about starting off horizontally, 80% of the functionality we have today will solve the use cases of those departmental users.”
Annie Pearl Sep 1, 2022 ▶ 7:15 Calendly CPO Annie Pearl: Hiring Advice for Product; Calendly's Second Product | 20VC #921 · 20VC with Harry Stebbings
Sep 1, 2022 neutral
Assertion Not checkable as stated
Pearl: Every major PLG company must add direct sales
“Every iconic PLG company, whether it's Slack or Dropbox or Asana or Zoom, you know, at some point they have to add on that sort of direct selling motion to complement the PLG business.”
Annie Pearl Sep 1, 2022 ▶ 10:17 Calendly CPO Annie Pearl: Hiring Advice for Product; Calendly's Second Product | 20VC #921 · 20VC with Harry Stebbings
Sep 1, 2022
Insight
Pearl: Prematurely hiring enterprise sales reps causes failure and excess costs
“Going too early can be detrimental, right? Hiring a bunch of sales rep when there isn't demand creates a bunch of noise. It creates extra costs for the organization. And ultimately, you know, those reps aren't going to be successful.”
Annie Pearl Sep 1, 2022 ▶ 10:57 Calendly CPO Annie Pearl: Hiring Advice for Product; Calendly's Second Product | 20VC #921 · 20VC with Harry Stebbings
Sep 1, 2022
Insight
Annie Pearl: Product strategy should span two to three years and review quarterly
“A realistic time horizon for kind of the combination of the product vision and strategy is call it two to three years. And I think that you then take that strategy... I think you reevaluate it quarterly. I mean, it doesn't mean you're going to change it quarte…”
Annie Pearl Sep 1, 2022 ▶ 41:16 Calendly CPO Annie Pearl: Hiring Advice for Product; Calendly's Second Product | 20VC #921 · 20VC with Harry Stebbings
Sep 1, 2022
Insight
Pearl: Visionary founders should hire operational CPOs, not visionaries
“The mistakes that I see happen is that the CEO founder goes to hire for a skill set that is either at odds with what they really need, or they're not actually honest with themselves around the role that they want to continue to play within product. And so if y…”
Annie Pearl Sep 1, 2022 ▶ 26:06 Calendly CPO Annie Pearl: Hiring Advice for Product; Calendly's Second Product | 20VC #921 · 20VC with Harry Stebbings
Sep 1, 2022 bullish
Prediction Not checkable as stated
Pearl: Calendly will expand to own the entire meeting lifecycle
“The third phase where I think we'll go eventually is beyond that and to really try to own and help support and deliver on the entire meeting life cycle. So scheduling is really just a wedge into a much broader meeting lifecycle. That's everything before the me…”
Annie Pearl Sep 1, 2022 ▶ 6:19 Calendly CPO Annie Pearl: Hiring Advice for Product; Calendly's Second Product | 20VC #921 · 20VC with Harry Stebbings
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