Supra Insider

Welcome to another episode of Supra Insider. This time, Marc and I are excited to bring you our conversation with John Cutler. John writes The Beautiful Mess, a popular Substack newsletter in the product community and frequently posts on LI to his 100k followers. We both learned about John’s work during his time at Amplitude, where he spent 4.5 years as a product evangelist and coach for hundreds of product teams around the globe, giving him a unique vantage point about reality on the ground in many different environments and cultures. John legitimately lives in the “matrix of product management”.Prior to Amplitude, John held product management roles at Zendesk and Pendo, and drove UX research at AppFolio. John recently left his role at Toast, where he focused on product enablement and is enjoying beautiful Santa Barbara while exploring what’s next.In this episode, we covered topics including:* John’s path from product management into product evangelism and the tradeoffs of making that transition* How the role of product management has evolved and where it might go* Why it’s important not to follow frameworks blindly and understand the context* The benefits writing has on John’s thinking and how consistent publishing has allowed him to build a personal brand, creating optionality in his career* John’s take on the great feature factory vs empowered product team debate and Marty Cagan’s episode on Lenny’s Podcast* And much more!John is an extremely nuanced thinker and truth seeker who wants to help bring the product world closer together. We think you’ll love this conversation.Links* John’s LI: https://www.linkedin.com/in/johnpcutler/* John’s blog (The Beautiful Mess): * Elena Verna: https://www.linkedin.com/in/elenaverna/John’s post about Marty Cagan’s episode on Lenny (Product Theater): This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit suprainsider.substack.com

In this episode, Marc and Ben are joined by Brenton Sellati. Brenton is the incoming VP of product at Pie Insurance (Series D insurtech company) where he will be leading the product and design team and leveraging his past experience driving innovation strategy and product management at Liberty Mutual Insurance where he started his product career.Between Liberty Mutual and Pie Insurance, Brenton had a stellar run for over 5 years at Wayfair, where he worked his way up from managing 4 teams as a group PM all the way to leading 50 teams as a senior director of product management. This episode goes into the secret sauce that enabled Brenton to scale as a leader supporting 300+ people. Our conversation covered a lot of ground:* Why most middle managers are not competent* How to build high trust, high candor relationships with people* Ways to create true leverage as your scope of management grows* Why it’s impossible to have clear thinking without clear writing* The importance of designing organizations to minimize cross-org dependencies * And a lot more!Brenton is one of the most structured thinkers we’ve met in product leadership. He’s a member of the Supra community and a consistent contributor to top of mind discussions within the group. We feel very lucky to get to learn from him on a weekly basis and the density of insights in the conversation might warrant listening twice - we know you’ll enjoy this conversation. Thanks for listening!Episode Links* Brenton’s LI: https://www.linkedin.com/in/brentonsellati/* Brenton’s Substack: brentonsellati.substack.com* Article: The day you became a better writer (Dilbert)* Doc: Sanitized reflections doc from 2019 at Wayfair* Nikhyl Singhal’s post about superpowers and shadows* 1v1 Norm & Expectation Setting template (Building Trust & Setting Expectations for Managers - the full written voiceover for the template)* Monthly Portfolio Review for Senior Leaders template (How Brenton managed his time at the Sr Director/VP level)* Strategic Task Backlog Example (How Brenton managed his time when he was a senior IC and early manager of 3-4 teams)Hosts* Marc: https://www.linkedin.com/in/marcbaselga/* Ben: https://www.linkedin.com/in/benerez/ This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit suprainsider.substack.com

Welcome to another episode of Supra Insider!In this episode, Marc and Ben are joined by Diana Kimball Berlin, a Partner at Matrix who invests in early-stage B2B SaaS & AI companies, from concept to Series A. Diana also sits on the boards of Accord and Meshcapade. Prior to becoming an investor, Diana spent 5 years at Quip, working up from an IC product manager to VP of Product. Before Quip, Diana was a senior PM at SoundCloud and has held roles at Kickstarter and Microsoft. In our chat with Diana, we cover a lot of ground:* Diana’s path from a liberal arts major to product management and investing* Why Diana likes liberal arts as a background for PMs and investors* How publishing writing has benefitted Diana in her life and career and why people should consider being more open with sharing their thinking (and what leaders can do to support their team in being more public online)* When founders should consider hiring their first product manager* What makes for the best relationships between CEOs and product executives* How product leaders can gauge compatibility with a company* And more!Diana is an extremely thoughtful investor and product leader. We hope you enjoy this conversation and look forward to hearing your feedback. Thanks for listening!Links* Diana’s LI: https://www.linkedin.com/in/dianakimball/* Diana’s website: https://dianaberlin.com/* Diana’s Substack* Diana’s post about whether business school is worth it for PMs: https://dianaberlin.com/posts/the-mba-decision-guide-for-product-managers * Lina Colucci: https://www.youtube.com/@Lina_ColucciHosts* Marc: https://www.linkedin.com/in/marcbaselga/* Ben: https://www.linkedin.com/in/benerez/ This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit suprainsider.substack.com

Welcome to another episode of Supra Insider. Following up on last episode’s discussion of the current PM market (episode 3), we wanted to add a new perspective to the conversation by inviting a product management recruiter to the show. In this episode, Marc and I are joined by James Jordan, the founder of Producto, a recruiting agency focused on PM hiring from ICs all the way to executives. James is coming up on two decades in recruiting and has a wealth of knowledge about the historical product management hiring landscape and the latest trends. If you’re thinking about hiring a PM or are a PM looking for a new role, you’ll love this conversation.In our chat with James, we cover a lot of ground:* James’s read on the current PM hiring market and what’s changed in the last year* Why do companies struggle to define what they want in their first PM hire?* We also discussed how people managers are struggling to break into senior IC roles, how he evaluates ICs vs. execs, and his unique approach to doing references* We conclude our chat discussing how most candidates are not using LI right, sleeping on networking, and where is the role of the Product going in the next couple of years.I hope you enjoy this conversation and look forward to hearing your feedback. Thanks for listening!Links* James Jordan: https://www.linkedin.com/in/jamesjordanrecruitment* Producto: https://productotalent.com* Product toolkit by Ravi Mehta - https://www.ravi-mehta.com/product-manager-roles/Hosts* Marc: https://www.linkedin.com/in/marcbaselga/* Ben: https://www.linkedin.com/in/benerez/ This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit suprainsider.substack.com

This is a wild market for product managers. The hiring landscape has shifted more in the last year than it did in the previous decade.With hundreds of thousands of people actively looking for their next role, we thought it would be helpful to invite a couple of folks from the Supra community to have a chat about how to navigate this job market. For those unfamiliar with Supra, it’s an invite-only community for elite product leaders that Marc founded.In this episode, Ben and Marc were joined by Gaurav Hardikar (VP Product @ HomeLight who mentors a ton of PMs who are changing roles) and Andrew Chapello (FinTech product leader who was recently in the market for the first time after 8 years and successfully ran a super intentional search).Our conversation covered a ton of ground, including:* How the PM market has changed in the last 6-12 months* How to set yourself up for success as a candidate in this market* Tips on getting interviews * Why cold applications and cover letters are a waste of time* Advice for running due diligence on companies before accepting offers* And more!If you’re on the market for your next product role or thinking about it, we think you’ll find this conversation relevant and actionable - thanks for listening!Links* AI Resume generator Teal/otta* Loom – recording yourself for your narrative.Guests* Gaurav Hardikar (https://www.linkedin.com/in/ghardikar/)* Andrew Chapello (https://www.linkedin.com/in/chapello/) Hosts* Marc: https://www.linkedin.com/in/marcbaselga/* Ben: https://www.linkedin.com/in/benerez/ This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit suprainsider.substack.com

Josh Doody has coached 200+ high earners in tech through salary negotiations, leading to an average of 16% increase in liquid first year compensation. He’s a published author of Fearless Salary Negotiation and shares tips regularly on YouTube.In this episode, we talk about:* Why people should negotiate* What’s a typical negotiation timeline* How to negotiate without a counteroffer* Go over common negotiation pitfalls/mistakes * How to negotiate in the current job market (Q1 2024)* Why changing companies every 2-3 years optimizes earning potentialIf you enjoyed the episode, feel free to learn more about Josh through these links:* Josh’s site: https://fearlesssalarynegotiation.com/* How to answer “What’s your expected salary?”: https://fearlesssalarynegotiation.com/salary-expectations-interview-question/ * Do you need multiple competing job offers to negotiate?: https://fearlesssalarynegotiation.com/multiple-competing-job-offers-negotiate/* Josh’s newsletter: https://fearlesssalarynegotiation.com/newsletter/* Twitter/X: https://twitter.com/JoshDoody* Linkedin: https://www.linkedin.com/in/joshdoody/* YouTube: https://www.youtube.com/@TheJoshDoody* Book: https://www.amazon.com/Fearless-Salary-Negotiation-step-step/dp/0692568689Thanks for listening!Marc & BenMarc: https://www.linkedin.com/in/marcbaselga/Ben: https://www.linkedin.com/in/benerez/Did you find this episode valuable? We’d appreciate a share!Want the next episode directly in your inbox? Subscribe below 👇 This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit suprainsider.substack.com

We’re excited to start sharing some of the interesting topics from the Supra product leadership community. Let us know if you have any feedback on the episode!You can also watch our conversation video on YouTube.Thanks for listening,Marc: https://www.linkedin.com/in/marcbaselga/Ben: https://www.linkedin.com/in/benerez/“How should I think about joining an early stage startup as their first product hire?” Many experienced product leaders are considering this path, so we sat down to chew on it together. In this episode, we talk about our respective journeys in early stage startups, the evaluation criteria we would apply today to the decision (including how to assess PMF, gauging fit with the founder and the team, the importance of the problem space, how compensation factors into the decision, and how your product craft could accelerate from a tour of duty in the very early stage). We wrap by describing the product leaders who might benefit the most from early stage startups and share a few tips from Supra community members.If you find this episode valuable, please rate the podcast on Spotify and share it with your friends. Thanks for listening!* Thanks to Supra community members Gaurav Hardikar and Joshua Herzig-Marx for contributing to this episode’s discussion.Learn more about the Supra product community.How to exercise your expiring stock options without financial risk or paying any $ out of pocket: Services like ESO Fund will provide you with cash to exercise your stock options. Learn more here: https://www.esofund.com/Did you find this episode valuable? We’d appreciate a share!Want the next episode directly in your inbox? Subscribe below 👇 This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit suprainsider.substack.com