How small product teams build big impact

Jason Chen

with Jason Chen

Co-founder & Head of engineering @ Trestle

Introduction & The Importance of Cohesion in Product Teams

- Value of Team Cohesion: The discussion opens with the recognition that team cohesion is often under-appreciated but is crucial for effective product collaboration and achieving excellent outcomes.
- Empathy for End Users: Jason stresses that the best advice he received is to always consider the end user, regardless of discipline. Every team member's unique user perspective contributes to a better product.

Building Product with User-Centered Mindset
- Multidisciplinary Collaboration: Jason highlights that product development involves multiple disciplines (engineering, design, marketing, etc.), each bringing valuable insights by thinking from their own user experiences.
- Role of User Research: He underscores the balance between internal assumptions and formal user research, emphasizing that user insights should be brought into conversations early, not just after research is complete.

Jason Chen’s Career Path & Lessons Learned

- Professional Development: Jason shares his journey from coder to co-founder, describing roles in special effects, startups, agencies, and a large video game corporation, and how exposure to diverse environments shaped his thinking.
- Learning from Experience: He reflects on the importance of learning from mistakes—such as focusing too much on engineering over maintenance and client usability—and how maturity enabled him to better handle broader responsibilities

Growth through Responsibility and Capability

- Expanding Beyond Technical Roles: Early in his career, Jason saw himself as focused purely on engineering, but over time, he contributed to design, product strategy, and marketing, learning the value of participating outside strict responsibilities.
- Communication & Self-Challenge: He advocates professionals should consider not just what is their responsibility, but what they are capable of contributing or communicating, fostering career growth by stepping outside comfort zones.

Evolving Product Development: AI and ‘Vibe Coding’
- Impact of AI and Solo Development: The conversation explores the trend of “vibe coding” and AI-driven development, where individuals can ship more with fewer resources, but may risk less robust products compared to multi-disciplinary teams.
- Communication Remains Key: Despite technological advances, Jason maintains that communication—internal and external—remains essential to ensuring quality and alignment, even as AI takes over more execution-oriented tasks.

Addressing Product Maintainability, Scalability, and Hidden Work
- Importance of Forward Thinking: Jason stresses that product owners should move beyond a reactive stance, forecasting edge cases, scalability, and ongoing maintenance to avoid persistent problems.
- Product Manager Advice: He recommends PMs continue asking fundamental questions about scalability, maintainability, and risk, regardless of whether tasks are human or AI-driven, highlighting that AI does not absolve teams from these concerns.

AI Limitations, Adoption, and Industry Adjustments
- Trust and Limits of AI: There is an in-depth discussion around the limitations of current AI—such as reliance on black-box prototypes and the impact of training data quality—alongside optimism for its place in future workflows.
- Adapting to Change: Both speakers agree that AI is now a permanent part of the landscape, and organizations/individuals must adjust by focusing on skills (like communication) that AI cannot easily replicate.

High-Performing Product Teams & Cohesion

- Team Cohesion as a Differentiator: Jason identifies his current team at Trestle as his best experience, attributing success to strong alignment, transparency, and communication, which reduces uncertainty and friction.
- Cohesion Requires Intentional Effort: He argues that team cohesion doesn’t happen organically and should be an explicit team goal, supported by feedback rituals such as weekly retrospectives to keep alignment high and interactions effective.

Final Thoughts & Call to Action
- Encouragement to Prioritize Team Cohesion: Jason advises teams to deliberately invest energy in building cohesion and alignment, as these are foundational to productive collaboration and positive outcomes.
- Promotion of Trestle: The episode concludes by encouraging viewers, especially contractors and vendors, to check out Trestle for innovative, AI-powered compliance and risk management solutions.