Nickey Skarstad is a Director of Product Management at Duolingo, where she is leading a stealth 0 → 1 product. Prior to Duolingo, she was VP of Product at The Wing, Product Lead at Airbnb, where she led much of the Experiences product team, Product Lead at Shopify, and Director of Product Management at Etsy.—Thank you to our wonderful sponsors for making this episode possible:• Mixpanel: https://mixpanel.com/startups• Dovetail: https://dovetailapp.com/lenny• Unit: https://unit.co/lenny—In this episode:[3:32] An overview of Nickey’s career[7:39] What she learned from building product at Airbnb[8:42] How to maintain and operationalize product quality[9:44] Metrics that help you maintain quality[20:08] Which company has most informed her product development approach[21:57] How to structure your product org[24:47] Should you go GM vs. functional[27:18] How you set vision, translate that into goals, and then execute on it[32:30] Brainstorming advice[35:04] How to use OKRs effectively[37:57] How to get better at influence as a PM[41:23] How to know if a decision is a one-way or two-way door[42:29] Second-order decisions, and second-order thinking[46:35] Operationalizing principles[47:17] Getting your team on board with your strategy[49:39] Designing a product review meeting[54:08] Tips for working remotely as a PM[56:44] Lightning round—Find the full transcript at: https://www.lennysnewsletter.com/p/nickey-skarstad-airbnb-etsy-shopify—Where to find Nickey:• Newsletter: https://nickey.substack.com/• TikTok: https://www.tiktok.com/@nickeyskarstad• LinkedIn: https://www.linkedin.com/in/nickeyskarstad/• Twitter: https://twitter.com/NickeySkarstad—Referenced:• Thinking in Systems by Donella H. Meadows• Anne Helen Petersen• Superhuman• Loom Get full access to Lenny's Newsletter at www.lennysnewsletter.com/subscribe

Manik Gupta has led two of the most successful consumer products in history—Google Maps, where he was Director of product for the Maps team, and Uber, where he was CPO. After leaving Uber, he spent some time working on a product to help people avoid getting COVID called CVKey, and most recently he took on a role at Microsoft as Corporate Vice President leading many of their consumer efforts.—Thank you to our wonderful sponsors for making this episode possible:• Mixpanel: https://mixpanel.com/startups• Coda: http://coda.io/lenny• Unit: https://unit.co/lenny—In this episode, we cover:[3:55] Patterns for career success[7:19] Why it’s valuable to be optimistic about technology[13:54] Challenges and mistakes through Manik’s career[17:28] How you learn the most about yourself through challenges[20:25] What Manik’s learned about building successful consumer apps[26:18] The importance of company-product fit[30:02] “The consumer stack”—what your company needs to have in place to build a successful consumer product[36:22] The path from PM to CPO[39:19] Evolution of CPO role[44:40] What leads to promotions in a PM career[47:58] What creates inflections in one’s PM career [52:05] How PMs shoot themselves in the foot[55:05] What it’s like to work at Google vs. Uber vs. Microsoft[1:01:35] What he wished he built into Google Maps—Where to find Manik:• LinkedIn: https://www.linkedin.com/in/manikg/• Twitter: https://twitter.com/manikgupta Get full access to Lenny's Newsletter at www.lennysnewsletter.com/subscribe

Merci Grace has been a founder, an investor (at Lightspeed Ventures), head of product and growth (at Slack), and is now a founder again (Panobi). She’s also one of the co-founders of Women in Product, and Fast Company named her one of the Most Creative People in 2017.—Thank you to our wonderful sponsors for making this episode possible:• Dovetail: https://dovetailapp.com/lenny• Mixpanel: https://mixpanel.com/startups• Whimsical: https://whimsical.com/lenny—In this episode, we cover:[3:41] Merci’s path to Head of Product and Growth at Slack[4:42] What Merci learned from being a VC that helps her be a better founder[6:50] How to tell a compelling story[9:43] What most people don’t know about Slack[10:27] Why Slack hasn’t created a consumer/social product[15:14] How Slack innovated the PLG motion[17:14] Slack’s early growth strategy[19:57] Slack’s activation point[22:10] Why it’s important to find connectors within a company[26:40] Lessons from optimizing Slack’s onboarding flow[32:12] Most common mistakes in going PLG[35:56] Signs you can go PLG[38:10] PLG vs. bottom-up[40:23] Importance of day-zero value in your tool[42:17] When to bring in your first salesperson[44:47] How to hire amazing people [50:21] Storytelling and Slack’s culture[51:04] How and when to build a growth team[52:08] How to build a more diverse team—Where to find Merci:• Panobi: https://panobi.com/• LinkedIn: https://www.linkedin.com/in/merci/• Twitter: https://twitter.com/merci• Website: https://mercigrace.co/• Women in Product: https://www.womenpm.org/ Get full access to Lenny's Newsletter at www.lennysnewsletter.com/subscribe

Sanchan Saxena is VP of Product at Coinbase. Before Coinbase, Sanchan was Head of Product and GM at Airbnb, founder and Head of Product of Instagram Shopping, Director of Product Management at Yahoo, and Lead PM at Microsoft.—Thank you to our sponsors for making this episode possible:• Dovetail: https://dovetailapp.com/lenny• Persona: https://withpersona.com/lenny• Productboard: https://www.productboard.com/—In this episode, you’ll learn:[3:50] How Sanchan worked his way up to VP of Product at Coinbase[6:15] Sanchan’s best advice to early-stage PMs[9:41] What to look for in a company to join[12:09] What Sanchan learned from Airbnb[16:40] Behind the scenes of how Airbnb survived the Covid downturn when travel completely stopped[21:49] How Airbnb tactically planned in two-week cycles[25:00] How to keep morale up during a disaster[29:00] What Sanchan learned from Brian Chesky, Brian Armstrong, and Kevin Systrom[36:08] How to know when to trust your gut vs. A/B testing[41:57] How Coinbase makes decisions[46:30] How teams use the RAPID decision-making process[47:00] How to operate in an ambiguous industry like web3[49:00] How to know if you should get into web3[51:46] How to hire and close amazing candidates[54:40] What to look for in product leaders[57:13] Lightning round—Where to find Sanchan:• LinkedIn: https://www.linkedin.com/in/sanchans/• Twitter: https://twitter.com/sanchans Get full access to Lenny's Newsletter at www.lennysnewsletter.com/subscribe

Teresa Torres is an internationally acclaimed author, speaker, and coach. She teaches a structured and sustainable system for continuous discovery that helps product teams infuse their daily product decisions with customer input. She’s coached hundreds of teams at companies of all sizes, from early-stage startups to global enterprises, in a variety of industries. She has taught over 11,000 product people discovery skills through the Product Talk Academy and hundreds through her coaching practice, and is the author of Continuous Discovery Habits.—Thank you to our sponsors for making this episode possible:• Persona: https://withpersona.com/lenny• Dovetail: https://dovetailapp.com/lenny• Stytch: https://stytch.com/—In this episode, we cover:[3:37] How Teresa is in the top 5 people in the world who’s helped the most PMs.[5:25] What is the “opportunity solution tree framework”?[8:19] What’s an example of an opportunity solution tree, for Netflix?[14:17] Why do we usually approach opportunity finding wrong?[18:10] What should you do if your company is a feature factory?[21:00] What is continuous discovery, and why is it so important?[23:13] What do you do if your leaders tell you there’s no time for user research?[25:55] How can you automate weekly conversations with customers?[29:04] How do you stay unbiased as a PM about a potential solution?[31:23] Should a PM have more say over other functions?[35:33] What are Teresa’s best tips for how to interview customers?[39:57] What’s the most common mistake people make while interviewing customers?[40:25] How does discovery change as your company grows?[43:27] When should you do user research and when should you run an experiment?—Where to find Teresa:• Product Talk: https://www.producttalk.org/• Opportunity solution tree: https://www.producttalk.org/opportunity-solution-tree/• Continuous Discovery Habits: https://www.amazon.com/Continuous-Discovery-Habits-Discover-Products/dp/1736633309• LinkedIn: https://www.linkedin.com/in/teresatorres/• Twitter: https://twitter.com/ttorres Get full access to Lenny's Newsletter at www.lennysnewsletter.com/subscribe

Brandon Chu is VP of Product at Shopify, where he leads the app platform ecosystem, new initiatives group, and M&A investments. Brandon helped scale Shopify’s PM team from five to hundreds, and worked his way up from an IC Senior PM. Prior to Shopify, he was a Director of PM at FreshBooks and, before that, a founder. Brandon might be best known for his writing on the art and science of product management as part of a collection on Medium he calls “The Black Box of Product Management.”—Thank you to our sponsors for making this episode possible:• Stytch: https://stytch.com/• Persona: https://withpersona.com/lenny• PostHog: https://posthog.com/lenny—In this episode, we cover:1) Brandon’s path to VP of Product at Shopify.2) What has Brandon found to be the most important skill set for super-successful PMs?3) What is it like to build product at Shopify?4) How did Shopify adjust after the shock to e-commerce during Covid?5) How did Shopify build a one-click team offsite flight/hotel/activity booking platform?6) How did Brandon motivate himself to start, and keep, writing?7) As a PM, why is writing one of the highest-ROI uses of your time?8) What’s Brandon’s favorite piece of writing?9) What are the biggest surprises, pros, and cons about being a platform PM?—Where to find Brandon:• Twitter: https://twitter.com/brandonmchu• LinkedIn: https://www.linkedin.com/in/brandonmchu/• Brandon’s writing: https://blackboxofpm.com/• Making Good Decisions as a Product Manager: https://blackboxofpm.com/making-good-decisions-as-a-product-manager-c66ddacc9e2b Get full access to Lenny's Newsletter at www.lennysnewsletter.com/subscribe

Elena Verna has led growth at some of today’s most successful B2B businesses, including Miro as CMO, Surveymonkey as SVP of Growth, and now at Amplitude as interim Head of Growth. She’s also worked closely with over a dozen companies on growth and product strategy, including companies like MongoDB, Clockwise, and Netlify (where she sits on the board of directors). Elena is undoubtedly one of the smartest people on growth strategy in the world.—Thank you to our sponsors for making this episode possible:• Persona: https://withpersona.com/lenny• Stytch: https://stytch.com/• PostHog: https://posthog.com/lenny—In this episode, we cover:1) How did Elena go from an analyst at Safeway to Head of Product at Amplitude?2) What’s changing in B2B growth?3) What exactly is “product-led growth,” and how can you apply it at every stage of growth?4) How is PLG already transforming itself?5) Why do you need to be both product-led and sales-led?6) Why does PLG often get crushed when you move upmarket, and how do you avoid this?7) What it looks like when your PLG motion is dying.8) Why product-led is the future of sales.9) Why is freemium the way to go, over trial?10) Why should you hire internally for your first growth hire?—Where to find Elena:• LinkedIn: https://www.linkedin.com/in/elenaverna• Twitter: https://twitter.com/elenaverna Get full access to Lenny's Newsletter at www.lennysnewsletter.com/subscribe

Before getting into teaching full-time, Gibson Biddle was VP of Product at Netflix and CPO at Chegg (a textbook rental and homework help company). He now spends his days speaking, writing, and hosting workshops on product leadership, strategy, and culture. There are very few people in the world who’ve worked with, and had an impact on, more product managers.—Thank you to our sponsors for making this episode possible:• Flatfile: flatfile.com/lenny• Coda: coda.io/lenny• PostHog: posthog.com/lenny—In this episode, we cover:1) Gibson’s career path to VP of Product at Netflix, CPO at Chegg, and eventually teaching full-time.2) The DHM model: The 3 factors of a product strategy for consumer companies, how you can apply it to your product strategy, and how Gibson used this model for decisions made at Netflix.3) Five mini case studies of the DHM model that could be applied to Netflix’s strategy.4) The GEM prioritization model: What are the 3 areas a company can optimize on? What is the fundamental misalignment that destroys startups? 5) How could you start building your product strategy muscle, even when you’re only two weeks into your new role?6) Building your personal board of directors.7) What does it take to become a CPO someday?8) What specifics in a daily routine separate a good product manager from a great product manager?9) What’s the one piece of advice Gibson has for product managers in their early career?—Where to find Gibson:• Ask Gib Product Newsletter: https://askgib.substack.com/• Gibson’s baby website: www.gibsonbiddle.com• Intro to product strategy: https://gibsonbiddle.medium.com/intro-to-product-strategy-60bdf72b17e3 Get full access to Lenny's Newsletter at www.lennysnewsletter.com/subscribe

Jackie Bavaro is the author of the best-selling books Cracking the PM Interview and Cracking the PM Career. She was most recently at Asana, where she joined as its first product manager and later became the head of product. Earlier in her career, Jackie was a PM at Google and Microsoft, where she worked on high-impact products such as Google Search and Microsoft SharePoint.In this episode, we cover:1. How did Jackie become head of product at Asana? Start writing the best-selling PM books on interviews and the career ladder?2. How and why to find a product coach.3. What are the downsides of being a manager? How do you know if you want to go into management?4. Can you stay an IC vs. becoming a manager?5. What is “strategy”? What are the 3 components of a strategy?6. What makes a good/bad strategy?7. What are some ways to get better at strategy?8. When should you start to invest in building your strategy muscle?9. What are signs that your strategy is off?10. What’s Jackie’s best piece of career advice?11. Why is it smart to join a big company?12. What are some of the most common mistakes PMs make early in their career?13. What is the one thing Jackie thinks every PM should do regardless of their level?Where to find Jackie:- Twitter: https://twitter.com/jackiebo - Books: Cracking the PM Interview and Cracking the PM Career: https://amzn.to/3If6X9U- Medium: ​​https://jackiebo.medium.comReferences:- Jackie’s book rec: Getting Things Done, by David Allen- Current favorite app, Paprika: https://www.paprikaapp.com- Favorite Twitter: https://twitter.com/hels - PEARL framework: https://jackiebo.medium.com/interview-tips-for-senior-pms-2424f7b7c967- Eigenquestions: https://coda.io/@shishir/eigenquestions-the-art-of-framing-problemsThank you to our amazing sponsors:* Flatfile: www.flatfile.com/lenny* Amplitude: www.amplitude.com* PostHog: www.posthog.com/lenny Get full access to Lenny's Newsletter at www.lennysnewsletter.com/subscribe

Gokul Rajaram serves on the executive team at DoorDash, where he leads the Caviar product line. Previously he worked at Square, where he was also on the executive team and led a number of key product lines, and as a product director at Facebook, where he helped the company transition its advertising business to become mobile-first. Earlier in his career, Gokul was a product director for Google AdSense, where he helped launch the product and grow it into a substantial portion of Google’s business. Gokul also serves on the boards of Coinbase, Pinterest, and The Trade Desk and is a prolific angel investor, having invested in companies like Airtable, Khatabook, and 100+ more.In this episode, you will learn:1. How to navigate your next career - What should you focus on in order to improve your optionality?- What should you consider as you look for your next career adventure?- Why join winners in a space?- Why should people entering the workforce join mid-stage companies?- Why there are many paths to success.2. How to build a product development process at early-stage companies- What does the best product development process typically look like at different company stages? - What are some common pitfalls when building these processes?3. Hiring PMs- When should you hire your first PM? What should you look for?- When should you wait longer to hire a PM?- What’s the number one secret for hiring a product leader, regardless of industry? - How much time should you allocate for hiring as a founder?- How might job titles impact your company’s work culture?4. How to start angel investing - How did Gokul start investing in startups? What would he have done differently?- What does he look for in a startup pitch? - How much time should you spend as a part-time investor? - How do you find deals as a new investor?Where to find Gokul:- Twitter: https://twitter.com/gokulr References:- Gokul’s current favorite app, Coinbase Wallet: https://www.coinbase.com/wallet - Favorite book, Playing to Win: How Strategy Really Works: https://rogerlmartin.com/lets-read/playing-to-win - TED talk: TEDxConcordia - Lenny Rachitsky - Losing Serendipity —Thank you to our sponsors for making this episode possible:• Amplitude: https://amplitude.com/• Flatfile: https://flatfile.com/Lenny• Productboard: https://Productboard.com/ Get full access to Lenny's Newsletter at www.lennysnewsletter.com/subscribe