Welcome to the UNLEARN Podcast! Today, we’re joined by a thought leader and prolific voice in product management and organizational design, John Cutler. With a unique ability to navigate the “beautiful mess” of product development, John has spent his career exploring the complex overlaps of product, UX, and strategy.

Currently serving as Head of Product at Dotwork, John has previously held impactful roles such as Senior Director of Product Enablement at Toast and Product Evangelist at Amplitude, where he collaborated with thousands of product teams worldwide. His extensive experience spans B2B SaaS giants like Zendesk, Pendo, and AppFolio, as well as B2C, ad-tech, banking, and media industries.

Known for his insightful writing, John has authored nearly a thousand posts across various platforms, captivating readers with his deep understanding of product dynamics. Whether you’re seeking to level up your product thinking or gain practical tips on team enablement, John’s expertise offers unparalleled insights.

Key Takeaways:

The Beautiful Mess of Product Development: John’s approach to embracing complexity and context in product management to uncover innovative solutions.
Unlearning and Growth: How letting go of rigid practices and adapting to change can unlock greater potential for teams and leaders.
Writing as a Catalyst for learning: The power of consistent writing in shaping ideas, refining strategies, and building meaningful connections in the product community.

Additional Insights:

Product Ecosystems in Flux: John talks about the dynamic nature of product management, highlighting how roles and best practices evolve with organizational and market shifts.
Gamifying the Creative Process: Insights into how John uses tools and techniques to make writing, ideation, and problem-solving more engaging and productive.
Rethinking Organizational Models: Exploring how companies can overcome challenges by reimagining structures, roles, and team dynamics for the modern era.

Get ready for a thought-provoking conversation with John Cutler on embracing complexity, fostering innovation, and mastering the art of unlearning!

Episode Highlights:

00:36 - Episode Introduction

"I don't think we need a product manager for every 4 to 7 people. A software as a service company is much more of a service ecology."

01:15 - Introducing John Cutler

"John is one of the most insightful voices in product management, with a career spanning roles at Toast, Amplitude, and beyond."

03:46 - Discovering the "Beautiful Mess" of Product

"I’ve always been fascinated by the overlaps—where product, UX, and strategy collide in unpredictable ways."

11:27 - The Importance of Writing and Sharing Ideas

"I realized that writing wasn’t just for others—it was for me to process and refine my thinking."

15:59 - Finding Your Path Through Experimentation

"Everybody finds their way if you're willing to experiment and try. It's like software—the rate of iteration and the velocity of creation allow you to refine and improve over time."

33:06 - Lessons in Unlearning

"It’s not just about adopting new practices; it’s about letting go of the ones that no longer serve the team or the context."

40:59 - What Excites John About the Future of the Industry

"The future of product management lies in embracing complexity and experimenting with new ways to scale and deliver value."

Follow Our Guest

LinkedIn Accounts:

John Cutler: www.linkedin.com/in/johnpcutler/
Dotwork: www.linkedin.com/company/dotworklabs/
Toast: www.linkedin.com/company/toast-inc/
Amplitude: www.linkedin.com/company/amplitude-analytics/
Zendesk: www.linkedin.com/company/zendesk/
Pendo: www.linkedin.com/company/pendo-io/

Websites:

_________________________________

Download my free innovation map I use to help companies like Google and Nike figure out the gap between their current state and desired state.

Download Now: https://bit.ly/InnovationPortfolioWorkbook

FOLLOW THE HOST:

LinkedIn: https://www.linkedin.com/in/barryoreilly
Personal site: https://barryoreilly.com
Facebook: https://www.facebook.com/barryoreillyauthor/
Twitter: https://x.com/barryoreilly
Instagram: https://www.instagram.com/barryoreilly/
Email: hello@barryoreilly.com