Supra Insider

Welcome to another episode of Supra Insider. This time, Marc and Ben sat down with Brenton Sellati, VP of Product at Pie Insurance, and Joshua Herzig-Marx as the honorary co-host for this episode to dive into the transformational journey of implementing the product operating model at Pie Insurance.

Brenton shares how he overhauled Pie’s product strategy, slashing 66% of the roadmap to focus on high-ROI initiatives, aligning leadership, and fostering a product-led culture. With insights from Joshua throughout the discussion, the episode explores the challenges and successes of introducing a problem-first mindset, building cross-functional collaboration, and creating a transparent prioritization system.

This episode is packed with actionable advice for product leaders and executives looking to drive organizational change and implement sustainable product practices.

All episodes of the podcast are also available on Spotify, Apple and YouTube (video).

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

To support the podcast, please check out the links below:

* Preparing for a PM interview with tech companies like Meta, Google, Microsoft, and OpenAI? Check out Ben's Maven bootcamp for Product Sense and Analytical Thinking PM interviews. Supra Insider listeners get 10% off with promo code “suprainsider”.

* Want to connect with product leaders like you? Check out Supra, an invite-only community with 350+ product leaders. You'll get matched with a group of 6-8 carefully vetted individuals and participate in a monthly session facilitated by a world-class coach. Last year, members reported solving their top product challenges 3x faster through these sessions. Plus, tap into our vibrant Slack community for "behind closed doors" topics, join exclusive speaker events with industry pioneers, and connect at intimate roundtables and in-person meetups.

In this episode, we covered the following topics:

* How Brenton implemented the product operating model to transform Pie Insurance’s product strategy

* The decision-making process behind slashing 66% of the roadmap and refocusing on high-ROI initiatives

* The importance of transparency and a data-driven approach to prioritization

* Challenges of transitioning to a problem-first mindset and how Pie Insurance’s leadership aligned to support the change

* Practical advice for empowering cross-functional teams and building a culture of continuous improvement

* Insights on fostering alignment and navigating organizational change

* And much more!

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

Links:

* Brenton Sellati: https://www.linkedin.com/in/brentonsellati/

* Joshua Herzig-Marx: https://www.linkedin.com/in/joshuaherzigmarx/

* Ben: https://www.linkedin.com/in/benerez/

* Marc: https://www.linkedin.com/in/marcbaselga/

If you enjoyed this conversation, please share it with a friend or colleague 👇

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And here are some less recent favorites:

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 Ben sat down with Peter Walker, Head of Insights at Carta. Drawing from Carta's vast database of over 30,000 companies, Peter offers a data-driven analysis of the evolving compensation landscape in 2024.

The conversation delves deep into product management compensation, exploring both cash and equity components across different startup stages. Peter shares unique insights into critical industry challenges, including the complexities of equity exercise decisions and the growing emphasis on capital efficiency in startups.

The episode tackles pressing questions facing the PM industry today: How are junior PMs navigating the competitive job market? What's driving the surge in fractional roles? How are executive hiring patterns shifting? Peter also illuminates AI's transformative impact across various functions and its implications for the future of work.

This thought-provoking discussion offers key insights for founders, product managers, and anyone interested in understanding the current dynamics of the startup ecosystem.

All episodes of the podcast are also available on Spotify, Apple and YouTube (video).

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

In this episode, we covered the following topics:

* How salaries and equity have shifted in 2024

* Why only 30% of employees are exercising their options and the factors behind it

* Differences in compensation between early-stage and late-stage startups

* The evolving hiring landscape: challenges for junior PMs and opportunities for senior ICs

* How capital efficiency is redefining startup hiring practices

* The rise of fractional roles and their impact on product management

* AI’s influence on various functions and its future trajectory in startups

* And much more!

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

Links:

* Peter Walker: https://www.linkedin.com/in/peterjameswalker/

* Carta: https://carta.com/

* Carta’s salary benchmark tool: https://carta.com/friend/

* Ben: https://www.linkedin.com/in/benerez/

* Marc: https://www.linkedin.com/in/marcbaselga/

If you enjoyed this conversation, please share it with a friend or colleague 👇

Also, if you’re a new subscriber, we encourage you to check out some of the recent episodes you might have missed:

And here are some less recent favorites:

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 Ben sat down with Alvaro Morales, CEO and co-founder of Orb, a company revolutionizing modern billing infrastructure with notable customers like Vercel, Perplexity, and Replit.

Alvaro shared his journey from being an engineering manager at Asana to launching Orb after encountering challenges with pricing iterations.

He also discussed the evolving role of pricing in product strategy and the rise of usage-based and outcome-based pricing models. Additionally, he shared his insights into the psychology behind pricing decisions, the importance of building customer trust, and how Orb's platform enables cross-functional teams to refine pricing with the same speed and efficiency as their product updates.

If you're a product, engineering, or finance leader curious about transforming your pricing strategy or building more agile processes, this conversation is packed with actionable insights.

All episodes of the podcast are also available on Spotify, Apple and YouTube (video).

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

In this episode, we covered the following topics:

* How Alvaro’s experiences at Asana inspired the creation of Orb

* The challenges modern teams face with pricing

* The psychology of pricing and how customer trust plays a pivotal role

* Outcome-based pricing as the “holy grail” and why it’s so difficult to achieve

* How Orb helps companies make pricing a dynamic, strategic advantage

* Alvaro’s journey with early design partners to refine Orb’s pricing

* Key trends in freemium, reverse trials, and usage-based pricing

* And much more!

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

Links:

* Alvaro Morales: https://www.linkedin.com/in/alvaro-morales/

* Alvaro Morales X: https://x.com/alvaromorales

* Orb: https://www.withorb.com/

* Alvaro Morales Email: [email protected]

* Ben: https://www.linkedin.com/in/benerez/

* Marc: https://www.linkedin.com/in/marcbaselga/

If you enjoyed this conversation, please share it with a friend or colleague 👇

Also, if you’re a new subscriber, we encourage you to check out some of the recent episodes you might have missed:

And here are some less recent favorites:

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 Ben sat down with Teresa Torres, author of Continuous Discovery Habits, to explore the role of AI in modern product discovery. Teresa shared why customer empathy remains irreplaceable, the common pitfalls teams face when misusing AI in research, and practical strategies for integrating AI effectively—without losing sight of the human touch.

She also offered her insights on how AI can empower product teams to build skills, enhance customer interviews, and streamline discovery workflows, all while staying firmly rooted in authentic customer understanding. If you're passionate about truly knowing your customers and using AI as a tool—not a crutch—this episode is brimming with valuable takeaways!

All episodes of the podcast are also available on Spotify, Apple and YouTube (video).

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

In this episode, we covered the following topics:

* Why AI can enhance but never replace human-driven customer research

* The pitfalls of relying on synthetic users and autogenerated personas

* How to use AI as a “team member” to synthesize interviews and uncover insights

* Importance to building curiosity and empathy into product teams

* Practical use cases for AI in discovery, including feedback analysis and research repositories

* Exciting experiments Teresa is running with AI to help PMs hone their interviewing skills

* The importance of owning your audience and the challenges of modern social media platforms

* And more!

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

Links:

* Teresa Torres: https://www.linkedin.com/in/teresatorres/

* Teresa Torres X: https://x.com/ttorres

* Product Talk: https://www.producttalk.org/

* Product Talk Daily Substack: https://producttalkdaily.substack.com/

* Product Talk Videos: https://videos.producttalk.org/

* Ben: https://www.linkedin.com/in/benerez/

* Marc: https://www.linkedin.com/in/marcbaselga/

If you enjoyed this conversation, please share it with a friend or colleague 👇

Also, if you’re a new subscriber, we encourage you to check out some of the recent episodes you might have missed:

And here are some less recent favorites:

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 Ben sat down with Tal Raviv, an experienced product manager and AI enthusiast, to explore the intersection of AI and productivity in product management. Tal shares insights from his career, including his time as the first PM at Riverside and his work building generative AI features.

We dove deep into the myths surrounding AI's role in product management, the power of context when working with tools like Claude and ChatGPT, and practical use cases for both co-pilots and agents. Tal also shared tips on creating a personal productivity system and how product managers can use AI to become more effective and impactful in their roles. Whether you're new to AI or looking to level up your approach, this episode has something for you.

All episodes of the podcast are also available on Spotify, Apple and YouTube (video).

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

In this episode, we covered the following topics:

* The myths surrounding AI in product management and its potential to reshape workflows

* The distinction between AI co-pilots and agents and their applications in work

* Practical use cases for leveraging AI tools like Claude to enhance productivity

* Building a personal productivity system to manage tasks, time, and stress effectively

* How foundational productivity skills amplify the effectiveness of AI tools

* Exploring the balance between offloading routine tasks and improving strategic thinking

* Insights into career transitions, solopreneurship, and redefining personal success

* Predictions for the future of AI's role in product management

* Inspiration and practical advice for professionals at all levels

* And more!

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

Links:

* Tal Raviv: https://www.linkedin.com/in/talsraviv/

* Tal’s Maven Course: https://maven.com/tal-raviv/product-manager-productivity-system

* Claude: https://www.claude.ai

* Reflect: https://reflect.app/

* Granola: https://www.granola.ai/

* Grain: https://grain.com/

* Ben: https://www.linkedin.com/in/benerez/

* Marc: https://www.linkedin.com/in/marcbaselga/

If you enjoyed this conversation, please share it with a friend or colleague 👇

Also, if you’re a new subscriber, we encourage you to check out some of the recent episodes you might have missed:

And here are some less recent favorites:

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 Ben sat down with Sunil (Sunny) Chaudhary, a former product leader turned recruitment director at Riviera Partners, one of the top recruiting firms in tech.

Sunny shares his journey from leading product teams to helping companies hire the right product leaders, offering a unique perspective from both sides of the hiring table.

In this episode, Sunny also dives deep into how the product leadership market is evolving, from the rising demand for AI expertise to the increasing focus on doers over managers. He shares actionable advice for candidates on standing out in competitive hiring processes, breaking into AI roles, and navigating compensation trends for super senior ICs and managers.

Whether you’re a product leader looking to land your next role or a founder hiring for a critical product position, Sunny’s insights into market trends, recruiter dynamics, and interview best practices are invaluable.

All episodes of the podcast are also available on Spotify, Apple and YouTube (video).

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

In this episode, we covered the following topics:

* How hiring priorities are changing and the rise of specialized product roles

* What companies are looking for in AI product leaders and how candidates without AI experience can position themselves

* Key strategies and traits of the top 1% of candidates in product leadership

* How senior IC roles are catching up with or surpassing managerial positions in pay and equity

* The current state of workplace flexibility and its impact on hiring

* And more!

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

Links:

* Sunil (Sunny) Chaudhary: https://www.linkedin.com/in/sunilchaudhary/

* Ben: https://www.linkedin.com/in/benerez/

* Marc: https://www.linkedin.com/in/marcbaselga/

If you enjoyed this conversation, please share it with a friend or colleague 👇

Also, if you’re a new subscriber, we encourage you to check out some of the recent episodes you might have missed:

And here are some less recent favorites:

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 Ben sat down with Gibson Biddle, former VP of Product at Netflix and Chief Product Officer at Chegg. Gib shares his journey from full-time product leadership to becoming an interim and fractional executive, driven by the desire to live life on his own terms. He discussed his strategies for balancing impact and flexibility, the importance of continuous learning, and his passion for teaching and storytelling.

Gib also talked about building engaging content, like his well-loved product strategy workshops, and organizing the Product Leader Summit. Whether you're a product leader looking for practical insights or someone seeking inspiration to live a more fulfilling life, this episode has something for you.

All episodes of the podcast are also available on Spotify, Apple and YouTube (video).

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

In this episode, we covered the following topics:

* Gib’s transition from traditional product roles to fractional CPO work

* The motivation behind semi-retirement and redefining success personally and professionally

* Strategies for scaling impact as a product leader through content, including talks and courses

* The importance of structured feedback and how Gib uses NPS to improve his presentations

* How Gib engages audiences in both in-person and virtual settings

* Key lessons from organizing the Product Leader Summit and what makes it unique

* Insights from Gib’s first cohort on Maven and his plans for future workshops

* Reflections on balancing life and work through meaningful experiments and adventures

* And more!

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

Links:

* Gib’s website: https://www.gibsonbiddle.com/

* Gib’s Substack: https://askgib.substack.com/

* Gib’s upcoming Maven Course: https://maven.com/gibson-biddle/product-strategy-short-workshop

* Gib’s Medium Articles: https://gibsonbiddle.medium.com/

* Gib’s 2023 Pacific Crest Trail backpack trip updates

* Gib’s LI: https://www.linkedin.com/in/gibsonbiddle/

* Ben: https://www.linkedin.com/in/benerez/

* Marc: https://www.linkedin.com/in/marcbaselga/

If you enjoyed this conversation, please share it with a friend or colleague 👇

Also, if you’re a new subscriber, we encourage you to check out some of the recent episodes you might have missed:

And here are some less recent favorites:

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

Today’s episode is a re-release of one of our most popular episodes on the podcast: our conversation with Josh Doody, a renowned salary negotiation coach and author of Fearless Salary Negotiation.

With the job market shifting and more people navigating complex career moves, we thought it was the perfect time to bring back Josh's invaluable advice on negotiating job offers.

This episode covers why changing companies can be key to maximizing your compensation, the best practices for salary negotiation, and common mistakes to avoid. It’s packed with practical strategies and tips to help you approach salary discussions with confidence and make the most of your opportunities. This is a must-listen for anyone preparing for interviews or hoping to elevate their career trajectory.

All episodes of the podcast are also available on Spotify, Apple and YouTube (video).

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

In this episode, we covered the following topics:

* Why changing companies every few years can significantly impact your compensation

* The key differences between negotiating within your current company vs. negotiating a new offer

* Common pitfalls to avoid during the negotiation process

* Why you should never reveal your salary expectations early in the conversation

* The most effective timeline for starting your negotiation preparation

* The role of market dynamics and how they influence salary discussions

* How to strategically use competing offers to your advantage

* And more!

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

Links:

* Fearless Salary Negotiation: https://fearlesssalarynegotiation.com/about/

* Josh Doody: https://www.joshdoody.com/

* Josh Doody’ YouTube: https://www.youtube.com/@TheJoshDoody

* Josh Doody LinkedIn: https://www.linkedin.com/in/joshdoody/

* Ben: https://www.linkedin.com/in/benerez/

* Marc: https://www.linkedin.com/in/marcbaselga/

If you enjoyed this conversation, please share it with a friend or colleague 👇

Also, if you’re a new subscriber, we encourage you to check out some of the recent episodes you might have missed:

 

And here are some less recent favorites:

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 Ben are joined by John Cutler and Joshua Herzig-Marx (friends of the show) to explore a growing trend in the product community: product leaders struggling to find their next roles.

We discussed the contributing factors to this trend, including the flattening of product organizations, the rise of super IC PMs, and the influence of AI. The conversation dives into practical advice for product leaders navigating these challenges and what the future might hold for product leadership.

For anyone who is navigating the evolving product management landscape, considering a career transition, or interested in how AI and organizational shifts are reshaping the role of product leaders, this episode is for you.

All episodes of the podcast are also available on Spotify, Apple and YouTube (video).

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

In this episode, we covered the following topics:

* The current trend of product leaders taking longer to find new roles

* Contributing factors such as the flattening of product organizations

* The role of AI in changing product leadership dynamics

* The emergence of the Super IC PM

* The impact of companies focusing on efficiency and reducing team sizes

* Advice for product managers in transition and those considering a role change

* Predictions for the future of product leadership in the next decade

* And more!

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

Links:

* Joshua Herzig-Marx: https://www.linkedin.com/in/joshuaherzigmarx/

* Joshua Herzig-Marx’s Website: https://jhm.lol/

* Carla Naumburg (JHM’s wife): https://www.carlanaumburg.com/

* John Cutler: https://www.linkedin.com/in/johnpcutler/

* John Cutler’s Substack: https://cutlefish.substack.com/

* Ben: https://www.linkedin.com/in/benerez/

* Marc: https://www.linkedin.com/in/marcbaselga/

If you enjoyed this conversation, please share it with a friend or colleague 👇

Also, if you’re a new subscriber, we encourage you to check out some of the recent episodes you might have missed:

And here are some less recent favorites:

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 Ben sit down with Ben Sprecher, CPO at an AI startup and a longtime product leader with 24 years of experience in AI. They explore Ben’s fascinating journey from founding a company that was acquired by Google to leading AI initiatives. In this episode, we dive into a futuristic bet Ben made 25 years ago on the future of AI, the concept of the "AI demo trap"—a pitfall many companies fall into—and actionable frameworks to avoid it.

If you’re a founder, product manager, or someone looking to enhance your AI strategy, this episode is packed with valuable insights and actionable advice to help you navigate the evolving landscape of Artificial Intelligence.

All episodes of the podcast are also available on Spotify, Apple and YouTube (video).

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

In this episode, we covered the following topics:

* Ben’s 25-year bet on AI and how close it came to reality

* The "AI demo trap" and how companies get stuck in it

* Frameworks for assessing AI projects that avoid common pitfalls

* Shifting from a defensive AI strategy to an offensive, disruptive approach

* Tips for product managers on adjusting the product development process for AI

* Practical steps to turn AI buzz into products that deliver real customer value

* And more!

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

Links:

* Ben Sprecher: https://www.linkedin.com/in/bensprecher/

* Ben: https://www.linkedin.com/in/benerez/

* Marc: https://www.linkedin.com/in/marcbaselga/

If you enjoyed this conversation, please share it with a friend or colleague 👇

Also, if you’re a new subscriber, we encourage you to check out some of the recent episodes you might have missed:

 

And here are some less recent favorites:

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