The most effective operators, dubbed 'dolphins,' can fluidly move between altitudes: operating strategically at 10,000 feet with founders, managing at 5,000 feet, and executing tactically in the weeds at 1,000 feet. This ability to oscillate is a key trait to hire for, especially in advisory or early-stage leadership roles.

Beyond vision and roadmaps, a CPO’s fundamental role is to act as a steward of the company's R&D investment. The primary measure of success is the ability to ensure that every dollar spent on development translates into tangible, measurable enterprise value for the business.

Pendo's CPO warns that scaling isn't just about replicating processes for more teams. Leaders must simultaneously build coordination systems (design reviews, clear communication) while fighting to maintain the "maniacal focus on the customer" and rapid innovation that characterize small teams.

Flexport's founder details his journey from a hands-off "manager mode" to a directive "founder mode." The rise of bottom-up AI innovation in hackathons is causing him to cycle back, recognizing the need to balance top-down strategy with empowering creative, decentralized ideas that leadership couldn't have conceived.

Moving from a large corporation to a startup requires blending foundational knowledge of scaling processes with newfound resourcefulness and risk appetite. This transition builds a holistic business muscle, not just a product one, by forcing leaders to operate without endless resources or established brand trust.

Rushing to implement a new strategy in a CPO role can be catastrophic. A structured 90-day plan prioritizes understanding nuance first. Spend the first 30 days on customer and team interviews, the next 30 drafting and aligning on strategy, and only begin executing changes in the final 30 days.

The traditional product management skillset is no longer sufficient for executive leadership. Aspiring CPOs must develop deep expertise in either the commercial aspects of the business (GTM, revenue) or the technical underpinnings of the product to provide differentiated value at the C-suite level.

As companies grow from 30 to 200 people, they naturally become slower. A CEO's critical role is to rebuild the company's operating model, deliberately balancing bottom-up culture with top-down strategic planning to regain speed and ensure everyone is aligned.

As you move up the product ladder, your strategic time horizon expands. ICs and Directors focus on quarters, VPs on the year, and CPOs must own the 3-5 year vision. Thinking long-term is a core CPO responsibility that no one else in the product organization will own.