Former product leader Aakash Gupta discusses the Product Leadership Job Search. Topics include hidden high-paying tech roles, importance of relationships with recruiters and VCs, and strategies for successful job interviews.

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

Brenton Sellati, VP at Pie Insurance, shares insights on scaling as a product leader: building high trust relationships, creating leverage, clear writing for clear thinking, minimizing dependencies. From managing 4 to 50 teams at Wayfair, his structured thinking shines. A masterclass in product leadership!

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

Founder of Supra, Marc, and VP Product Gaurav Hardikar and FinTech product leader Andrew Chapello discuss navigating the current product leadership job market. Topics include changes in the PM market, tips for success as a candidate, getting interviews, due diligence on companies, and more.

Josh Doody, a salary negotiation coach, discusses the importance of negotiation, common pitfalls, and strategies for maximizing earning potential. Topics include negotiating without a counteroffer, changing companies for higher salaries, and debunking fears of offer rescinding. Learn how to navigate salary negotiations effectively in the tech industry.

Exploring the decision to join an early stage startup as the first product manager, focusing on factors like product-market fit, team dynamics, founder alignment, and compensation. Discussing the benefits of honing product craftsmanship in a dynamic startup environment, navigating financial considerations, and the significance of early equity exercise. Insights shared on evaluating PMF, aligning with the team, and accelerating product growth in early stage startups.