71: John Cutler - How to structure a product organization

John Cutler on the challenges of scaling and operating a collaborative product organization. 

We discuss different mental models for how different functions work together as teams and why it’s important to clarify and document the operating model, especially during times of growth, turnover, or changing strategies.

John talks about the concept of scaffolding is introduced as a way to navigate the process of change and improvement and why most crossfunctional initiatives fail.

Takeaways

• Define in an operating model team sizes, roles, and responsibilities
• Reduce single points of failure and promote shared accountability
• Establish a shared language around team and domain evolution
• Stay firm on the chosen operating model and evaluate it within a specific timeframe

Sound Bites

• "We invest in teams, products, and outcomes, not individual projects and deliverables."
• "What are the valid reasons to ask for money and what kind of rigor are you going to put for them for their team?"
• "Teams respond well if there are a small number of things that people are stubborn about."

Chapters

06:45 The Need for an Operating Model in a Growing Company

08:04 Running a Collaborative Product Organization

14:32 The Challenges of the CPO and CTO Tandem

19:26 The Importance of Clarifying and Documenting the Operating Model

29:00 Scaffolding and Navigating Change

38:23 Team Size and Misalignment in SaaS Teams

39:18 Investing in Teams, Products, and Outcomes

41:27 Valid Reasons to Ask for Money and Team Rigor

45:03 The Importance of Being Stubborn

46:46 The Power of Enable Constraints

51:54 Defining Team Sizes and Roles

01:05:30 The Role of Engineering Managers in Teams

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