Supra Insider

#52: The beautiful mess of organizational context | John Cutler & Joshua Herzig-Marx

Apr 7, 2025

In this discussion, John Cutler, Head of Product at Dotwork, and Joshua Herzig-Marx, a mentor for startups, dive into the transformative impact of AI on product development. John shares his innovative approach at an early-stage startup, emphasizing a platform-first mindset and the importance of adaptable tools. They explore the rise of new roles in AI-native organizations and the potential of simulations to reshape decision-making. This conversation offers valuable insights for product leaders eager to embrace the evolving tech landscape.

01:09:13

Creator website

Episode guests

Josh Herzig-Marx

John Cutler

AI Summary

AI Chapters

Episode notes

Podcast summary created with Snipd AI

Quick takeaways

AI is driving a significant transformation in product development, enabling teams to deliver faster, customized solutions that address evolving customer needs.

The shift towards outcome-based pricing models emphasizes the importance of value alignment between organizations and their customers for sustainable growth.

Product operations teams are becoming integration engineers, utilizing AI tools to enhance efficiency, versatility, and adaptability in their roles amidst changing market dynamics.

Deep dives

The Impact of AI on Product Development

AI is transforming product teams by allowing for faster and more customized solutions. Companies can build on top of existing SaaS platforms to meet specific needs, effectively covering the gaps left by traditional products. This shift has prompted product executives to rethink their strategies, especially as industries observe significant changes in customer expectations and operational models. As organizations adapt, early adopters of AI-driven tools are gaining a competitive edge in product development and operations.

Intro

3min

Navigating Startup Dynamics

24min

Harnessing AI for Transformative Consulting Solutions

3min

Exploring Claude Projects and AI-Driven Learning Solutions

3min

Synthetic Companies and Organizational Intelligence

17min

Navigating Layers of Abstraction in Software Development

4min

AI-Driven Application Development

13min

Learning and Engaging: Navigating Organizational Context

3min

Welcome to another episode of Supra Insider. This time, Marc and Ben sat down with John Cutler and Joshua Herzig-Marx for a wide-ranging conversation about how AI is transforming the way product teams build, collaborate, and scale. John shares why he joined a new early-stage startup as Head of Product and how the team is breaking the traditional rules of product development—starting with a platform-first mindset.

The conversation explores the rise of highly configurable tools, the new personas emerging in AI-native organizations, and how simulations, knowledge graphs, and organizational ontologies might shape the next generation of work. Whether you're a product leader, founder, or operator curious about the frontier of product ops and AI tooling, this episode offers tons of insight—and inspiration.

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

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

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

* Supra just launched its first Product Leadership compensation & tools benchmarks report. The report covers comp trends across different seniority tiers, work settings, and reporting structures. Want to get access to the full report? Please fill out this form to get your exclusive copy.

* Preparing for a PM interview with tech companies like Meta and Google? Check out Ben's course for Product Sense and Analytical Thinking PM interviews (selected by Lenny Rachitsky as a Top Course in Product on Maven 🔥) and the standalone AI Copilot for practice. Supra Insider listeners get 10% off the course with promo code “suprainsider”. Enrollment is now open for the next cohort starting April 22nd.

In this episode, we covered the following topics:

* Why John Cutler returned to full-time product leadership and what excites him about the role

* How platform-first thinking changes the way early-stage teams build and ship

* The importance of optionality and choosing the right design partners

* How AI is reshaping product ops—turning operators into builders and enabling faster experimentation

* The power (and limitations) of building synthetic organizations to simulate internal dynamics

* Why abstractions, ontologies, and knowledge graphs matter for collaboration in AI-era companies

* How product teams should approach pricing, packaging, and customer segmentation in a world of custom solutions

* And much more!

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

Links:

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

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

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

* 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

Remember Everything You Learn from Podcasts

Save insights instantly, chat with episodes, and build lasting knowledge - all powered by AI.

Supra Insider

#52: The beautiful mess of organizational context | John Cutler & Joshua Herzig-Marx

Episode guests

Podcast summary created with Snipd AI

Quick takeaways

Deep dives

The Impact of AI on Product Development

The Shifting Dynamics in SaaS Companies

The Role of Product Operations Teams

Navigating Customer Relationships in Early-Stage Startups

Rethinking Product Management and Pricing Strategies

Remember Everything You Learn from Podcasts