Calendly, every mention

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every year anyone Lenny Rachitsky 71Oji Udezue 15Sam Lessin 9Annie Pearl 9Austin Hay 4Chris Hutchins 2Naomi Ionita 1Kevin Yien 1Hila Qu 1Georgiana Laudi (Gia) 1

Verbatim, from the transcripts: the passages where Calendly comes up

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How to show up in any room with a low heart rate: Silicon Valley’s missing etiquette playbook Jan 15, 2026 · 9 mentions

  • ▶ 49:26 Sam Lessin Oh, well, like, I think I'd like to say that I'm fairly famous for hating Calendly. 9 times in the scene

How AI is reshaping the product role | Oji and Ezinne Udezue Sep 7, 2025 · 2 mentions

  • ▶ 1:17 Lenny Rachitsky Aji was Chief Product Officer at Calendly and Typeform, and led product teams at Twitter, Atlassian, and Microsoft.
  • ▶ 14:53 Oji Udezue Before I shipped anything at Calendly, I did the design review with a support manager.

Unorthodox PM tips: Automating user insights, unselling candidates, decision logs, more | Kevin Yien Aug 18, 2024 · 1 mention

  • ▶ 56:59 Kevin Yien Those then get pushed automatically to a Slack channel or otherwise, and then you can set up workflows, either via Zappi or something else, to say who was the customer, pull their email, put that into a sequence, drop in my Calendly, and…

Picking sharp problems, increasing virality, and unique product frameworks | Oji Udezue (Typeform) Sep 14, 2023 · 20 mentions

  • ▶ 0:58 Lenny Rachitsky At Calendly, where he was chief product officer. 2 times in the scene
  • ▶ 11:09 Lenny Rachitsky Is there an example that comes to mind of either Calendly or Typeform or Atlassian where you pushed it further up the frequency direction or the everyone direction?
  • ▶ 16:14 Oji Udezue Calendly is this weird company where people don't see all the value. 2 times in the scene
  • ▶ 32:07 Oji Udezue There's a version of that also that is what I call continuous conversations, which is a Calendly and a Typeform, which we'll do more and more of. 6 times in the scene
  • ▶ 41:05 Oji Udezue At Calendly, for example, we ask them about connecting their calendar,
  • ▶ 43:53 Lenny Rachitsky And I'm curious, do you have an example of what an activation milestone was at Calendly or Twitter or Typeform, just to give people a sense of like, here's a good example of an activated user milestone. 3 times in the scene
  • ▶ 53:04 Oji Udezue Remember before Cali, there was acuity scheduling. 5 times in the scene

The ultimate guide to Martech | Austin Hay (Reforge, Ramp, Runway) Aug 13, 2023 · 4 mentions

  • ▶ 1:15:51 Austin Hay I, like, I've been a big Calendly user for a long time, but Calendly is pretty expensive. 4 times in the scene

Building a long and meaningful career | Nikhyl Singhal (Meta, Google) Jun 11, 2023 · 1 mention

  • ▶ 6:18 Lenny Rachitsky I know the one person that self-identified was, uh, Annie Pearl from Calendly, who is a big advocate of the stuff that you do.

The ultimate guide to adding a PLG motion | Hila Qu (Reforge, GitLab) Apr 2, 2023 · 1 mention

  • ▶ 55:14 Hila Qu Think about, uh, Figma, think about like calendar-ly even, right?

Lessons from working with 600+ YC startups | Gustaf Alströmer (Y Combinator, Airbnb) Mar 2, 2023 · 4 mentions

  • ▶ 38:53 Lenny Rachitsky This reminds me of a story of just a recent podcast interview I did with the CPO of Calendly. 4 times in the scene

Behind the scenes of Calendly’s rapid growth | Annie Pearl (CPO) Feb 26, 2023 · 66 mentions

  • ▶ 0:39 Lenny Rachitsky Annie is currently Chief Product Officer at Calendly. 3 times in the scene
  • ▶ 4:10 Lenny Rachitsky I've got a Calendly question to kick things off. 10 times in the scene
  • ▶ 13:27 Lenny Rachitsky So I want to transition a little bit to talking about Calendly. 8 times in the scene
  • ▶ 23:54 Annie Pearl So, you know, when I joined Calendly, all of our ARR came from our PLG channel.
  • ▶ 25:15 Lenny Rachitsky I have a whole bunch of questions about how Calendly grows, and maybe we just get into some of the stuff, because I imagine a lot of people are interested. 6 times in the scene
  • ▶ 33:30 Annie Pearl At Calendly, we have this sort of vision, our winning aspiration, to become the best place to schedule, prepare for, and follow up on your external meetings. 2 times in the scene
  • ▶ 35:37 Lenny Rachitsky I'd love to know just how you do planning accountantly.
  • ▶ 39:40 Lenny Rachitsky So maybe on that topic, what are, what else is in the stack of Calendly product team tools?
  • ▶ 40:27 Lenny Rachitsky How did Calendly get their first thousand users? 8 times in the scene
  • ▶ 43:44 Annie Pearl Most people probably think about Calendly as the scheduling link and really for individual users to reduce the back and forth of email and scheduling, right? 6 times in the scene
  • ▶ 46:06 Lenny Rachitsky What are some funner, unique traditions and cultural kind of components of the Calendly product team? 2 times in the scene
  • ▶ 48:41 Lenny Rachitsky It sounds like it's kind of a, there's a pretty unique culture at Calendly. 6 times in the scene
  • ▶ 52:07 Lenny Rachitsky Before Calendly, you were at Box. 5 times in the scene
  • ▶ 54:46 Lenny Rachitsky I'm trying to imagine you using all three in the same day, sending a Calendly, storing your files in a box, and looking at reviews of- And recruiting. 2 times in the scene
  • ▶ 59:58 Lenny Rachitsky Final question, what's your best Calendly pro tip?
  • ▶ 1:00:45 Lenny Rachitsky We learned a ton about Calendly, growth, product building. 4 times in the scene

How to price your product | Naomi Ionita (Menlo Ventures) Jan 12, 2023 · 1 mention

Launching and growing a podcast | Chris Hutchins (All the Hacks, Wealthfront, Google) Dec 18, 2022 · 2 mentions

Build better products with continuous product discovery | Teresa Torres Oct 6, 2022 · 2 mentions

Customer-led growth | Georgiana Laudi (Forget The Funnel) Sep 29, 2022 · 1 mention

  • ▶ 6:28 Georgiana Laudi (Gia) But in mid 2017, I actually paired up with Claire Sellentrop who led marketing at Calendly and her and I have been working together since about mid 2017.
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