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-rapidWhere to find Annie Pearl:• LinkedIn: https://www.linkedin.com/in/anniepearl/• Email: Annie.Pearl@calendly.comWhere 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 roundProduction and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com. Get full access to Lenny's Newsletter at www.lennysnewsletter.com/subscribe

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?

Career transitions are filled with dozens of questions and pitfalls. Join Nikhyl Singhal and four product leaders from the Skip CPO group to discuss the challenges associated with big career decisions. Briana Ings (ClickUp), Anneka Gupta (Rubrik), Shirley Lin (Divvy Homes), and Annie Pearl (Calendly) bring dozens of years of leadership experience to the conversation, as they discuss when to leave (and not) leave your company, how to research the next opportunity, manage the interview process, and successfully interview and land that great next job. Don’t miss their inside tips on what they look for in interviews, common mistakes to avoid, and how they evaluate opportunities.Connect with The Skip: Newsletter | Podcast | CPO GroupFollow Nikhyl Singhal on LinkedIn | TwitterFollow Anneka Gupta on LinkedInFollow Annie Pearl on LinkedInFollow Brianna Ings on LinkedInFollow Shirley Lin on LinkedIn Full Show Notes:[0:00] Welcome to The Skip![1:30] Introducing our guests Anneka, Annie, Briana, and Shirley![3:30] Shirley Lin describes the company culture differences between Divvy Homes and Airbnb[6:00] The Skip Community for CPOs[8:30] “The head of product or a CPO role, it can be very lonely. You have a lot of pressure on you.”[12:00] Career errors, specifically in times of transitions into and out of roles[13:30] What to do when a company changes dramatically in size and/or in culture[14:30] “It was actually the point where I was frustrated, where I worked through those frustrations and helped solve those problems where I had the greatest growth. Both in terms of my title and getting responsibility, but also just from a personal level and having to figure out a way through those difficult times.”[17:30] Do good companies pass on good people?[21:30] Should you ask for feedback after an interview? Or after getting turned down for a position?[25:30] Pregnancy, life changes, and other times of absence[30:00] There really is no “one size fits all” for every career situation. Every person has a unique and personal journey to creating the career of their dreams[34:00] When looking for a new job, what is the process and where should you look first?[39:00] What does crafting a career framework look like?[45:00] A name with a well-known brand VS. a company that is a great unique fit for you[48:00] “It’s always easier to find a job when you have a job.”[54:00] Factoring in your seniority when thinking about finding a job (and leaving your current job)[1:01:00] Biggest pet peeves NOT to do in an interview![1:06:30] Interviewing and the “take-home” interview[1:13:00] How to decide which of your references to use for your interview and resume[1:15:00] Finding references for the company you are interviewing with or in other words interviewing in reverse.[1:16:30] Wisdom in determining if a company is worth joining or not[1:22:00] “Your boss doesn’t need to be your best friend.”  (And respect over friendliness)—-----The Skip podcast helps tech professionals get ahead in their career. It’s hosted by Nikhyl Singhal, a successful founder, head of product, and executive. He coaches more than 100 executives, managers, and rising stars navigate important career decisions, management challenges, and personal crossroads to maximize their happiness and professional life.

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?

In this podcast episode, Nikhyl is joined once again by Anneka Gupta, Annie Pearl, Briana Ings, and Shirley Lin. The group explores the topics of how to recognize and recover from burnout, as well as to achieve a healthy work-life balance. They discuss the personal nature of burnout and how it's not simply a matter of comparing the two columns of “work” and “life.” The group suggests that if you're feeling burnt out or unsure if you're on the right path, it's time to reflect on your work and make changes to achieve a more balanced state. Nikhyl advises aiming for the "yellow" as a North Star and taking corrective action to prioritize tasks and achieve a healthier state.Overall, the episode provides practical advice for anyone experiencing burnout, emphasizing the importance of self-reflection and taking action to achieve a healthier work-life balance. Nikhyl's advice to aim for a more balanced state and prioritize tasks is a helpful reminder that perfect balance may be unattainable, but making incremental changes can lead to significant improvements in mental and emotional well-being.Thanks to this group of incredible women for joining and sharing their endless wisdom. We hope to have further discussions on other big career topics. Please share the podcast with your friends :) Connect with The SkipThe Skip: Newsletter | Website | LinkedIn CPO GroupNikhyl Singhal: LinkedIn | Twitter | FacebookAnneka Gupta: LinkedIn | TwitterAnnie Pearl: LinkedIn | InstagramBrianna Ings: LinkedIn | InstagramShirley Lin: LinkedIn Full Show Notes:[0:00] Welcome to The Skip![0:10] Introducing our guests Anneka, Annie, Briana, and Shirley![0:30] Starting with Anneka Gupta, CPO of Rubik, Inc. - how does she handle “work/life balance?”[0:45] “I would phrase it not as ‘what do I have to fit into the box of my life’, but what do I want to fit into the box of my life?”[2:30] Brianna Ings - VP of Product at ClickUp - how does she handle work/life balance?[2:30] “I have a four month old daughter. And so the big thing for me is figuring out my new normal. So I really wanna prioritize spending time with my daughter, my husband, we used to have dinner together every night, and I wanna maintain that.”[4:00] How does Shirley Lin find joy in her life?[4:30] “my husband and I try to make sure we're connecting, but we confess, there are some nights where we kind of stand at the kitchen counter and we're eating a dinner of Salami, cheese and a glass of wine, and we're saying like, that's pretty good; good enough.“[5:30] Does being an experienced Project Manager help Annie Pearl, CPO of Calendly, decide how to effectively optimize her time?[9:00] As part of the new norm for Executives in the Zoom era, Briana vividly narrates her experience of multitasking; juggling between an important meeting, and keeping an eye on her baby daughter as she pumps breast milk.[11:30] Has anyone ever had to hold back professionally because of the need to balance time and commitments, even if it meant passing up a great opportunity at a top company?[15:45] In a graduation speech, Shonda Rhimes talked about the challenges of being a working parent. She said that whenever she appears to be succeeding in one area of her life, it often means she's struggling in another.[17:00] The additional pressures of being a working parents and the worry of the expectations of others[22:30] Many people are struggling with burnout and a sense of failure. To overcome this, it's essential to examine our relationship with work and make changes that will lead to a more fulfilling and sustainable path forward.[24:30] Nikhyl advises those feeling burnt out to aim for a more balanced state, using the "yellow" as a North Star. He emphasizes the importance of taking corrective action to prioritize tasks and achieve a healthier state, even if perfect balance is unattainable.[26:30] “There's always things that are going wrong, but can I find joy in growing and trying to get through the hardship?”[31:00] How do you make sure you prioritize yourself?[34:00] Briana struggled with saying "no" in her career, including a time when she was asked to travel for work despite not wanting to leave her daughter. She learned to prioritize her own desires and set boundaries by saying "no" when necessary, allowing her to feel more in control of her time.[36:00] Nikhyl shares his thoughts on the challenges of outsourcing and asks for personal tips from the group who are all working moms with busy schedules. Are there any "executive hacks"?[38:00] How does this group plan and schedule vacations?[46:00] Nikhyl advises leaders who are considering bigger, more demanding roles to check in and test their capacity before taking the plunge to avoid burnout.—-----The Skip podcast is designed to help tech professionals take control of their careers and achieve their professional goals. Hosted by Nikhyl Singhal, a successful founder, head of product, and executive, the podcast offers guidance on navigating important career decisions, management challenges, and personal crossroads.Nikhyl has helped hundreds of leaders in the tech industry maximize their happiness and professional life. He understands that career is one of the most critical parts of a person's identity and that many people struggle to navigate the complex landscape of job transitions, skills development, and long-term career planning.