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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\u2019s 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\u2019s 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:

\u2022 LinkedIn: https://www.linkedin.com/in/anniepearl/

\u2022 Email: Annie.Pearl@calendly.com

Where to find Lenny:

\u2022 Newsletter: https://www.lennysnewsletter.com

\u2022 Twitter: https://twitter.com/lennysan

\u2022 LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

Referenced:

\u2022 How to send a calendar invite with Calendly: https://calendly.com/blog/how-to-send-a-calendar-invite

\u2022 Google\u2019s APM program: https://careers.google.com/programs/apm/

\u2022 The 15 Best Associate and Rotational Product Manager Programs: https://medium.com/agileinsider/product-management-digest-apm-3c2631683139

\u2022 Playing to Win: How Strategy Really Works: https://www.amazon.com/Playing-Win-Strategy-Really-Works/dp/142218739X/

\u2022 Confluence: https://www.atlassian.com/software/confluence

\u2022 Aha: https://www.aha.io/

\u2022 Airtable: https://www.airtable.com/

\u2022 Loom: https://www.loom.com/

\u2022 Jira: https://www.atlassian.com/software/jira

\u2022 Pendo: https://go.pendo.io/

\u2022 Tope Awotona on LinkedIn: https://www.linkedin.com/in/bawotona/

\u2022 The Skip podcast: https://www.skip.community/

\u2022 Skip Community on LinkedIn: https://www.linkedin.com/company/skip-community-for-cpos/

\u2022 Nikhyl Singhal on LinkedIn: https://www.linkedin.com/in/nikhyl/

\u2022 Good to Great: Why Some Companies Make the Leap and Others Don\u2019t: https://www.amazon.com/Good-Great-Some-Companies-Others/dp/0066620996

\u2022 Hooked: How to Build Habit-Forming Products: https://www.amazon.com/Hooked-How-Build-Habit-Forming-Products/dp/0241184835/

\u2022 20VC podcast: https://www.thetwentyminutevc.com/

\u2022 Sing 2 on Netflix: https://www.netflix.com/title/81475311

\u2022 Miro: https://miro.com/

In this episode, we cover:

(00:00) Annie\u2019s 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\xa0

(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\u2019s customer base and adding sales\xa0

(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\u2019s product stack

(40:21) How Calendly got their first 1,000 users\xa0

(43:36) The surprising new growth levers at Calendly

(46:05) Fun traditions

(48:43) \u201cFocus wisely\u201d and other aspects of Calendly\u2019s 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.