Ever feel torn between wanting the impact and scope of a VP or CPO role and worrying about what you might lose along the way? If you’ve been reading job descriptions, Reddit threads, or career advice that all seem to contradict each other, you’re not alone. In part two of our product management career progression series, we get honest about what actually changes as you start aiming for executive product leadership.

We welcome back special guest David Nash to unpack the real work behind VP and CPO titles, and the parts no one puts on the career ladder diagram. We dig into how success gets measured differently, why influence matters more than authority, and what it really means to trade hands-on product work for organizational, financial, and people decisions. We also talk about how to prepare without rushing. What skills matter, how to spot roles that are set up to succeed, and how to stay grounded when the politics and ambiguity show up.

If you’re considering the VP or CPO path and want clarity instead of hype, pull up a chair on the porch. Learn from the scars, shortcut some hard lessons, and leave with a clearer sense of what to build toward next and whether this path is truly right for you.

Time Stamped Notes:

Introduction and Episode Overview
[00:00] framing part two of the product management career progression series
[01:30] why moving up is less about leveling up mindset and more about changing orientation and scope

Guest Introduction and Personal Context
[02:37] David Nash’s background as a multi-time CPO and why lived experience matters at this level
[03:50] personal milestones and rapport that ground the conversation in real leadership journeys

Transitioning from Director to VP
[04:26] the myth of empowerment and why more senior titles do not remove constraints
[06:46] the three Ps framework: product, practice, and people, with people becoming the dominant focus
[07:41] staying close enough to the work without drowning as the scope expands

Challenges and Strategies in Executive Product Leadership
[08:53] legacy products, uncomfortable trade-offs, and why old platforms often fund innovation
[10:40] unwritten strategy, executive subtext, and navigating ambiguity that is never documented
[17:41] balancing short-term delivery with long-term outcomes that executives and boards care about
[19:33] building alliances across the executive team to survive competing priorities

Leadership Trade-offs and Organizational Reality
[21:58] sacrificing product purity without losing intent as responsibility shifts toward the business
[26:49] the CPO mindset shift from product-first thinking to business-first accountability
[29:51] dysfunction at the executive level and why maturity does not magically appear with title

Personal Growth, Mentorship, and Meaning
[41:10] why mentoring and developing people becomes the most fulfilling part of leadership
[43:59] reflections on impact, legacy, and staying connected to why the work matters

Closing Reflections and Takeaways
[46:11] one-word takeaways capturing growth, trust, discomfort, and people
[47:26] final thoughts on preparation, clarity, and choosing the VP or CPO path intentionally

Help keep the Product Porch lights on by giving at https://www.patreon.com/TheProductPorch

Join our email list and never miss an episode at theproductporch.com

Becoming a VP & CPO: Leading Product at the Executive Level (Part 2)

The Product Porch