Annie Pearl

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

Annie Pearl

Chief Product Officer

Calendly

Annie Pearl is the CPO @ Calendly, the company that makes scheduling meetings simple and painless. Before Calendly, Annie led Glassdoor's product vision and user experience, managing a 70-person product and design org. Shreyas Doshi is an investor, advisor, and all-around product OG. Most recently Shreyas spent over 5 years at Stripe where he was Stripe's first PM Manager and helped grow the PM function (from ~5 to more than 50 people). Before Stripe, Shreyas was a Director of Product Management @ Twitter. David Lieb is one of the product OGs of the last decade. As the founder of Bump David pioneered how over 150M users shared data, contacts and more before the company was acquired by Google. At Google, David took this one step further by creating Google Photos. Marty Cagan is one of the OGs of Product and Product Management as the Founder of Silicon Valley Product Group. Before founding SVPG, Marty served as an executive responsible for defining and building products for Hewlett-Packard, Netscape Communications, and eBay. Aparna Chennapragada is the former CPO @ Robinhood, revolutionizing consumer finance with commission-free investing. Prior to Robinhood, she spent an incredible 12 years at Google, most recently as VP and GM for Consumer Shopping and also as the lead AR and Visual Search products. Lenny Rachitsky is one of the OGs of product, having spent over 7 years at Airbnb as a product lead he left to start his newsletter, find it here. This has scaled to thousands upon thousands of readers and one of the most popular newsletters on Substack. For the last 7 years, Kayvon Beykpour has been at Twitter where he led all of the teams across Product, Engineering, Design, Research, and Customer Service & Operations. Kayvon came to Twitter through Periscope, the live broadcasting app he founded that was acquired by Twitter in 2015. Scott Belsky is an entrepreneur, author, investor, and currently serves as Adobe's Chief Product Officer. Scott oversees all of product and engineering for Creative Cloud, as well as design for Adobe. In 2006, Scott founded Behance, and served as CEO until Adobe acquired Behance in 2012. In Today's Episode on How to Hire a Product Manager, We Discuss: 1.) When to Hire Your First PM: What are the core signs that the founder must delegate and hire their first PM? What are the first things that are breaking when you do not have one but need one? How does the timing of the first PM differ when comparing B2B vs B2C? 2.) What is the Right Profile: What should founders look for in this first PM hire? What traits make the best? What are the biggest red flags in the personalities and styles of potential candidates? Should they have experience in the product domain they are entering? What are the single biggest mistakes founders make when analyzing the resumes of potential PM candidates? What should they look for in their resume? 3.) The Hiring Process: How To Hire a Product Manager How do we structure and run the hiring process for this person? What tests can we do to understand if they have the skill set we need for the role? How do we structure a hiring panel to make this process more effective? What are the biggest mistakes founders make in the hiring process for PMs?

Annie Pearl

Chief Product Officer

Calendly

Shreyas Doshi

Advisor and Coach

SCShreyas Doshi ConsultingStripe

David Lieb

Director

GoogleY Combinator

Annie Pearl is the CPO @ Calendly, the company that makes scheduling meetings simple and painless. The company now has over 10M users around the world and over 50,000 companies loving the product. As for Annie, before Calendly, Annie led Glassdoor's product vision and user experience, managing a 70 person product and design org. Prior to Glassdoor, Annie led enterprise product teams at Box both before and after their 2015 IPO. If this was not enough, Annie is also on the Board of WorkRamp and Well Health. In Today's Episode with Annie Pearl We Discuss: 1.) Entry into Product From Consulting: How did Annie make her way into the world of product and come to lead product teams at Box and GlassDoor? What are 1-2 of her biggest takeaways from her time at Box and GlassDoor? How did they impact her product mindset? What does Annie know now that she wishes she had known when she started in product? 2.) PLG vs Enterprise: What, When, How: Is it possible to do PLG and top-down enterprise strategy together from Day 1? Why does every PLG company eventually have to adopt an enterprise strategy? What are the single biggest challenges companies face when moving to enterprise? How do founders know when is the right time to make this transition? How do founders need to restructure their org to make the transition to enterprise? 3.) Building the Product Bench: Hiring: When is the right time to hire your first product leader? What are the core signals? What are the core character traits needed for a first product leader? How do we specifically structure the interview to test for them? Who do we bring into the interview process from other parts of the org? Do we do case studies with candidates? If so, how long do they have with the data? What is the difference between good vs great with case studies? 4.) Product Strategy, Reviews and Alignment: How does Annie assess how often product strategy should be reviewed? When should it change? How does Annie approach post-mortems? What is the right way to structure them? How does Annie create alignment between sales and product? Why is this so important? What is the single biggest product mistake Annie has made? What did she learn?

Annie Pearl

Chief Product Officer

Calendly