Supra Insider

Welcome to another episode of Supra Insider. This time, we’re excited to bring you our conversation with Jeff Whitlock, CEO at Grain.

New to the pod? Subscribe below to get the next episode in your inbox 👇

Jeff’s most important job is as a father of three. His second most important job is as the CEO of Grain, a role he took on after holding a few other roles at the company, including President, Head of Product and Head of Operations.

Before Grain, Jeff started his career at McKinsey, then joined Vivint Smart Home. He’s held multiple product leadership roles in early stage startups, and co-founded multiple startups of his own (one of which went through YC in 2021).

In this episode, we talked about

* How the best product teams are using call recording software to bring their team along

* Why a product background makes Jeff a more effective CEO

* How Grain prioritizes building intuitive software in a crowded space including Jeff’s philosophy on killing features

* How Jeff creates space to be a good dad while running a company

* The exploding tech scene in Utah

* How Jeff builds conviction

* And more!

We loved chatting with Jeff and learned a ton. Hope you enjoy listening!

If you’d like to watch the video, you can catch that on YouTube:

Links:

* Jeff’s LI: https://www.linkedin.com/in/jeff-whitlock/

* Grain: www.grain.com

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. We changed things up for this episode and instead of Ben and Marc interviewing a guest, Ben interviewed Marc.

New to the pod? Subscribe below to get the next episode in your inbox 👇

In this episode, Marc and Ben dive deep into various aspects of the Supra community, including:

* Supra’s founding story

* The importance of curating a high-quality, committed member community and matching people into the right groups.

* The role of executive coaches in facilitating meaningful discussions and maintaining group engagement.

* Challenges faced in scaling the community as a bootstrapped business

* The value of in-person events and the desire to organize more of them in the future.

* Common career paths & aspirations of product leaders + how Supra aims to help

* Potential future opportunities for Supra.

If you're a product leader interested in learning more about Supra, reach out to Marc on LinkedIn. In the meantime, enjoy the episode!

And if you’d like to watch the video, you can catch that on YouTube:

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. This time, we’re excited to bring you our conversation with Nan Yu, Head of Product at Linear.

New to the pod? Subscribe below to get the next episode in your inbox 👇

Nan had a super interesting path to his current role: he started his career as a software engineer at Goldman Sachs, then served as the CTO of Everlane for nearly six years before joining Abstract as an engineering manager (where he paired with Ben as his primary PM counterpart). After a couple years at Abstract, Nan joined Mode Analytics initially as interim CTO and then as their full-time VP of Product.

In this episode, we went deep on how Linear:

* Designs its org and structures its teams

* Builds products (and how it uses Linear)

* Runs work trials to screen for fit

* and much more!

We had a blast talking to Nan and learned a ton from our conversation. Enjoy it!

If you’d like to watch the video, you can catch that on YouTube:

Links

* Nan’s LI: https://www.linkedin.com/in/thenanyu/

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. This time, we’re excited to bring you our conversation with Aakash Gupta.

New to Supra Insider? Subscribe to get each episode straight to your inbox 👇

Aakash is a former product leader who was most recently VP of Product at Apollo, Head of Product Growth at Affirm, and other great companies. He’s lately become known for his Substack newsletter, Product Growth, where he has a very large subscriber base, as well as his LinkedIn where he has 200k+ followers.

In this episode, we went deep on the latest Product Growth Substack post, titled The Product Leadership Job Search, covering the following topics:

* Aakash’s motivation for writing this article

* Definitions for what it means to be a product leader in this environment

* Biggest findings (and surprises) from researching the article, including that the best leadership jobs often aren’t posted

* Why it’s important to build and nurture relationships with product recruiters and venture capital teams

* How to set yourself up for successful relationships with hiring managers

Aakash brought a lot of energy and excitement to this conversation and we hope you enjoy it. Thanks for listening!

Episode Links

* Aakash LI: https://www.linkedin.com/in/aagupta/

* Aakash’s co-author Colin’s LI: https://www.linkedin.com/in/colinlernell/

* Aakash’s Substack:

* Article we discussed:

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. 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_Colucci

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. 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 potential

If 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/0692568689

Thanks for listening!

Marc & Ben

Marc: 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