Behind the scenes of Calendly’s rapid growth | Annie Pearl (CPO)

2023-02-26 · 62 min · 44 entities

episode page audio

Asserted relationships

→ references Playing Win Strategy Really Works book

0.77

evidence rules-v4
Link in episode "Behind the scenes of Calendly’s rapid growth | Annie Pearl (CPO)": https://amazon.com/Playing-Win-Strategy-Really-Works/dp/142218739X
→ references Good Great Some Companies Others book

0.77

evidence rules-v4
Link in episode "Behind the scenes of Calendly’s rapid growth | Annie Pearl (CPO)": https://amazon.com/Good-Great-Some-Companies-Others/dp/0066620996
→ references Hooked How Build Habit Forming Products book

0.77

evidence rules-v4
Link in episode "Behind the scenes of Calendly’s rapid growth | Annie Pearl (CPO)": https://amazon.com/Hooked-How-Build-Habit-Forming-Products/dp/0241184835
→ references Skip Community For Cpos company

0.77

evidence rules-v4
Link in episode "Behind the scenes of Calendly’s rapid growth | Annie Pearl (CPO)": https://linkedin.com/company/skip-community-for-cpos
→ references Product Management Digest Apm 3c2631683139 website

0.77

evidence rules-v4
Link in episode "Behind the scenes of Calendly’s rapid growth | Annie Pearl (CPO)": https://medium.com/agileinsider/product-management-digest-apm-3c2631683139
→ hosted by Lenny Rachitsky person

0.55

evidence rules-v4
Feed author/publisher: Lenny Rachitsky
→ discusses Technology company

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evidence rules-v4
Feed category: Technology
→ discusses Business concept

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evidence rules-v4
Feed category: Business
→ discusses Entrepreneurship concept

0.40

evidence rules-v4
Feed category: Entrepreneurship
→ references penname.co website

0.38

evidence rules-v4
Link in episode "Behind the scenes of Calendly’s rapid growth | Annie Pearl (CPO)": https://penname.co/
→ references miro.com website

0.38

evidence rules-v4
Link in episode "Behind the scenes of Calendly’s rapid growth | Annie Pearl (CPO)": https://miro.com/
→ references Software company

0.38

evidence rules-v4
Link in episode "Behind the scenes of Calendly’s rapid growth | Annie Pearl (CPO)": https://atlassian.com/software/jira
→ references airtable.com website

0.38

evidence rules-v4
Link in episode "Behind the scenes of Calendly’s rapid growth | Annie Pearl (CPO)": https://airtable.com/
→ references loom.com website

0.38

evidence rules-v4
Link in episode "Behind the scenes of Calendly’s rapid growth | Annie Pearl (CPO)": https://loom.com/
→ references thetwentyminutevc.com website

0.38

evidence rules-v4
Link in episode "Behind the scenes of Calendly’s rapid growth | Annie Pearl (CPO)": https://thetwentyminutevc.com/
→ references Confluence website

0.38

evidence rules-v4
Link in episode "Behind the scenes of Calendly’s rapid growth | Annie Pearl (CPO)": https://atlassian.com/software/confluence
→ references skip.community company

0.38

evidence rules-v4
Link in episode "Behind the scenes of Calendly’s rapid growth | Annie Pearl (CPO)": https://skip.community/
→ references go.pendo.io website

0.38

evidence rules-v4
Link in episode "Behind the scenes of Calendly’s rapid growth | Annie Pearl (CPO)": https://go.pendo.io/
→ references How To Send A Calendar Invite website

0.38

evidence rules-v4
Link in episode "Behind the scenes of Calendly’s rapid growth | Annie Pearl (CPO)": https://calendly.com/blog/how-to-send-a-calendar-invite
→ references Programs website

0.38

evidence rules-v4
Link in episode "Behind the scenes of Calendly’s rapid growth | Annie Pearl (CPO)": https://careers.google.com/programs/apm
→ references aha.io website

0.38

evidence rules-v4
Link in episode "Behind the scenes of Calendly’s rapid growth | Annie Pearl (CPO)": https://aha.io/

Entities found in this episode

websites 22

mentioned Product Management Digest Apm 3c2631683139 website

0.90

evidence rules-v4
Link in episode "Behind the scenes of Calendly’s rapid growth | Annie Pearl (CPO)": https://medium.com/agileinsider/product-management-digest-apm-3c2631683139
references Product Management Digest Apm 3c2631683139 website

0.77

evidence rules-v4
Link in episode "Behind the scenes of Calendly’s rapid growth | Annie Pearl (CPO)": https://medium.com/agileinsider/product-management-digest-apm-3c2631683139
mentioned penname.co website

0.45

evidence rules-v4
Link in episode "Behind the scenes of Calendly’s rapid growth | Annie Pearl (CPO)": https://penname.co/
mentioned miro.com website

0.45

evidence rules-v4
Link in episode "Behind the scenes of Calendly’s rapid growth | Annie Pearl (CPO)": https://miro.com/
mentioned airtable.com website

0.45

evidence rules-v4
Link in episode "Behind the scenes of Calendly’s rapid growth | Annie Pearl (CPO)": https://airtable.com/
mentioned loom.com website

0.45

evidence rules-v4
Link in episode "Behind the scenes of Calendly’s rapid growth | Annie Pearl (CPO)": https://loom.com/
mentioned thetwentyminutevc.com website

0.45

evidence rules-v4
Link in episode "Behind the scenes of Calendly’s rapid growth | Annie Pearl (CPO)": https://thetwentyminutevc.com/
mentioned Confluence website

0.45

evidence rules-v4
Link in episode "Behind the scenes of Calendly’s rapid growth | Annie Pearl (CPO)": https://atlassian.com/software/confluence
mentioned go.pendo.io website

0.45

evidence rules-v4
Link in episode "Behind the scenes of Calendly’s rapid growth | Annie Pearl (CPO)": https://go.pendo.io/
mentioned How To Send A Calendar Invite website

0.45

evidence rules-v4
Link in episode "Behind the scenes of Calendly’s rapid growth | Annie Pearl (CPO)": https://calendly.com/blog/how-to-send-a-calendar-invite
mentioned Programs website

0.45

evidence rules-v4
Link in episode "Behind the scenes of Calendly’s rapid growth | Annie Pearl (CPO)": https://careers.google.com/programs/apm
mentioned aha.io website

0.45

evidence rules-v4
Link in episode "Behind the scenes of Calendly’s rapid growth | Annie Pearl (CPO)": https://aha.io/
references penname.co website

0.38

evidence rules-v4
Link in episode "Behind the scenes of Calendly’s rapid growth | Annie Pearl (CPO)": https://penname.co/
references miro.com website

0.38

evidence rules-v4
Link in episode "Behind the scenes of Calendly’s rapid growth | Annie Pearl (CPO)": https://miro.com/
references airtable.com website

0.38

evidence rules-v4
Link in episode "Behind the scenes of Calendly’s rapid growth | Annie Pearl (CPO)": https://airtable.com/
references loom.com website

0.38

evidence rules-v4
Link in episode "Behind the scenes of Calendly’s rapid growth | Annie Pearl (CPO)": https://loom.com/
references thetwentyminutevc.com website

0.38

evidence rules-v4
Link in episode "Behind the scenes of Calendly’s rapid growth | Annie Pearl (CPO)": https://thetwentyminutevc.com/
references Confluence website

0.38

evidence rules-v4
Link in episode "Behind the scenes of Calendly’s rapid growth | Annie Pearl (CPO)": https://atlassian.com/software/confluence
references go.pendo.io website

0.38

evidence rules-v4
Link in episode "Behind the scenes of Calendly’s rapid growth | Annie Pearl (CPO)": https://go.pendo.io/
references How To Send A Calendar Invite website

0.38

evidence rules-v4
Link in episode "Behind the scenes of Calendly’s rapid growth | Annie Pearl (CPO)": https://calendly.com/blog/how-to-send-a-calendar-invite
references Programs website

0.38

evidence rules-v4
Link in episode "Behind the scenes of Calendly’s rapid growth | Annie Pearl (CPO)": https://careers.google.com/programs/apm
references aha.io website

0.38

evidence rules-v4
Link in episode "Behind the scenes of Calendly’s rapid growth | Annie Pearl (CPO)": https://aha.io/

companys 8

mentioned Skip Community For Cpos company

0.90

evidence rules-v4
Link in episode "Behind the scenes of Calendly’s rapid growth | Annie Pearl (CPO)": https://linkedin.com/company/skip-community-for-cpos
references Skip Community For Cpos company

0.77

evidence rules-v4
Link in episode "Behind the scenes of Calendly’s rapid growth | Annie Pearl (CPO)": https://linkedin.com/company/skip-community-for-cpos
mentioned Technology company

0.50

evidence rules-v4
Feed category: Technology
mentioned Software company

0.45

evidence rules-v4
Link in episode "Behind the scenes of Calendly’s rapid growth | Annie Pearl (CPO)": https://atlassian.com/software/jira
mentioned skip.community company

0.45

evidence rules-v4
Link in episode "Behind the scenes of Calendly’s rapid growth | Annie Pearl (CPO)": https://skip.community/
discusses Technology company

0.40

evidence rules-v4
Feed category: Technology
references Software company

0.38

evidence rules-v4
Link in episode "Behind the scenes of Calendly’s rapid growth | Annie Pearl (CPO)": https://atlassian.com/software/jira
references skip.community company

0.38

evidence rules-v4
Link in episode "Behind the scenes of Calendly’s rapid growth | Annie Pearl (CPO)": https://skip.community/

books 6

mentioned Playing Win Strategy Really Works book

0.90

evidence rules-v4
Link in episode "Behind the scenes of Calendly’s rapid growth | Annie Pearl (CPO)": https://amazon.com/Playing-Win-Strategy-Really-Works/dp/142218739X
mentioned Good Great Some Companies Others book

0.90

evidence rules-v4
Link in episode "Behind the scenes of Calendly’s rapid growth | Annie Pearl (CPO)": https://amazon.com/Good-Great-Some-Companies-Others/dp/0066620996
mentioned Hooked How Build Habit Forming Products book

0.90

evidence rules-v4
Link in episode "Behind the scenes of Calendly’s rapid growth | Annie Pearl (CPO)": https://amazon.com/Hooked-How-Build-Habit-Forming-Products/dp/0241184835
references Playing Win Strategy Really Works book

0.77

evidence rules-v4
Link in episode "Behind the scenes of Calendly’s rapid growth | Annie Pearl (CPO)": https://amazon.com/Playing-Win-Strategy-Really-Works/dp/142218739X
references Good Great Some Companies Others book

0.77

evidence rules-v4
Link in episode "Behind the scenes of Calendly’s rapid growth | Annie Pearl (CPO)": https://amazon.com/Good-Great-Some-Companies-Others/dp/0066620996
references Hooked How Build Habit Forming Products book

0.77

evidence rules-v4
Link in episode "Behind the scenes of Calendly’s rapid growth | Annie Pearl (CPO)": https://amazon.com/Hooked-How-Build-Habit-Forming-Products/dp/0241184835

concepts 6

mentioned Business concept

0.50

evidence rules-v4
Feed category: Business
mentioned Entrepreneurship concept

0.50

evidence rules-v4
Feed category: Entrepreneurship
mentioned Annie Pearl (CPO concept

0.42

evidence rules-v4
Behind the scenes of Calendly’s rapid growth | Annie Pearl (CPO)
discusses Business concept

0.40

evidence rules-v4
Feed category: Business
discusses Entrepreneurship concept

0.40

evidence rules-v4
Feed category: Entrepreneurship
mentioned CPO concept

0.35

evidence rules-v4
CPO

persons 2

mentioned Lenny Rachitsky person

0.70

evidence rules-v4
Feed author/publisher: Lenny Rachitsky
hosted by Lenny Rachitsky person

0.55

evidence rules-v4
Feed author/publisher: Lenny Rachitsky

Episode description as stored

Brought to you by Miro —A collaborative visual platform where your best work comes to life: https://miro.com/lenny | Coda —Meet the evolution of docs: https://coda.io/lenny | Vanta —Automate compliance. Simplify security: https://vanta.com/lenny — Annie Pearl is the Chief Product Officer at Calendly. Previously, she was Chief Product Officer at Glassdoor, as well as Director of Product Management at Box. She was named one of the most influential women in Bay Area business by the San Francisco Business Times . In today’s episode, Annie shares three paths into product management and advice on how to get your foot in the door. She also gives us an inside look at how Calendly’s product teams are structured, how they transitioned from solely PLG to adding a sales team and unlocking new growth levers, how they do planning, and much more. Find the full transcript here: https://www.lennysnewsletter.com/p/behind-the-scenes-of-calendlys-rapid Where to find Annie Pearl: • LinkedIn: https://www.linkedin.com/in/anniepearl/ • Email: Annie.Pearl@calendly.com Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • Twitter: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ Referenced: • How to send a calendar invite with Calendly: https://calendly.com/blog/how-to-send-a-calendar-invite • Google’s APM program: https://careers.google.com/programs/apm/ • The 15 Best Associate and Rotational Product Manager Programs: https://medium.com/agileinsider/product-management-digest-apm-3c2631683139 • Playing to Win: How Strategy Really Works : https://www.amazon.com/Playing-Win-Strategy-Really-Works/dp/142218739X/ • Confluence: https://www.atlassian.com/software/confluence • Aha: https://www.aha.io/ • Airtable: https://www.airtable.com/ • Loom: https://www.loom.com/ • Jira: https://www.atlassian.com/software/jira • Pendo: https://go.pendo.io/ • Tope Awotona on LinkedIn: https://www.linkedin.com/in/bawotona/ • The Skip podcast: https://www.skip.community/ • Skip Community on LinkedIn: https://www.linkedin.com/company/skip-community-for-cpos/ • Nikhyl Singhal on LinkedIn: https://www.linkedin.com/in/nikhyl/ • Good to Great: Why Some Companies Make the Leap and Others Don’t : https://www.amazon.com/Good-Great-Some-Companies-Others/dp/0066620996 • Hooked: How to Build Habit-Forming Products : https://www.amazon.com/Hooked-How-Build-Habit-Forming-Products/dp/0241184835/ • 20VC podcast: https://www.thetwentyminutevc.com/ • Sing 2 on Netflix: https://www.netflix.com/title/81475311 • Miro: https://miro.com/ In this episode, we cover: (00:00) Annie’s background (03:50) How to send a Calendly invite without feeling awkward (06:04) How to transition to product work from a non-technical career (09:53) APM programs (10:52) The characteristics of internal-transfer PMs (13:26) How Calendly structures product teams (14:57) Why Annie hired a Head of Design (16:58) How Calendly structures product teams (19:07) OKRs at Calendly (21:02) Changes made at Calendly to improve execution and shipping (22:45) The challenges with narrowing Calendly’s customer base and adding sales (25:21) Where 70% of new Calendly users come from (26:17) The transition from PLG to sales (29:23) How to build a great relationship with your sales team (31:52) Planning and prioritization at Calendly (38:14) Strategy documents at Calendly (39:39) Calendly’s product stack (40:21) How Calendly got their first 1,000 users (43:36) The surprising new growth levers at Calendly (46:05) Fun traditions (48:43) “Focus wisely” and other aspects of Calendly’s culture (52:07) Learnings from Box and Glassdoor (54:57) The Skip Community (58:10) Lightning round Production and marketing by https://penname.co/ . For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com . This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe