What separates the CPOs who scale with confidence from those who get stuck? In this podcast hosted by Sid Shaik, Pendo Chief Product Officer Trisha Price breaks down what the best CPOs get right when scaling enterprise software. She shares hard-earned lessons from scaling complex enterprise software, leading both vertical and horizontal product portfolios, and shaping product strategy in a fast-moving AI era.

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Show Notes

  1. A technical foundation helps product leaders navigate complex decisions and build stronger partnerships with engineering.
  2. Exposure to sales builds empathy for revenue teams and sharpens a product leader’s understanding of market pressures.
  3. Vertical and horizontal products demand entirely different approaches to strategy, prioritization, and discovery.
  4. Effective product leadership starts with aligning deeply to company strategy and the outcomes the business needs to achieve.
  5. The best CPOs reject feature-factory thinking and embrace accountability for revenue, win rates, and churn.
  6. A differentiated point of view on the market and the product’s direction is essential for long-term success.
  7. Scaling from a single scrum team to dozens requires clarity in communication, design reviews, and unified experience standards.
  8. Hiring the right people becomes the defining factor in scaling both teams and product velocity.
  9. Roadmaps must stay dynamic, transparent, and outcome-anchored rather than output-anchored.
  10. Usage analytics and value-moment tracking offer faster insight into product effectiveness than traditional status reporting.
  11. Early design partners are critical when measuring the success of new features, especially for long-cycle or on-prem deployments.
  12. Product-led and sales-led motions strengthen each other when combined intentionally in enterprise B2B.
  13. AI now enables product teams to discover insights at scale by analyzing sales calls, support tickets, and customer trends.
  14. Product operations and analytics teams play increasingly important roles in enabling data-driven decision-making.
  15. Emerging AI tooling dramatically accelerates the path from idea to prototype, reshaping PM workflows.
  16. Customers now expect insight-rich, automated, and agent-powered experiences across all software.
  17. Post-IPO companies must balance short-term commitments with long-term innovation to avoid sliding into consulting-driven development.
  18. Dedicated innovation teams can work, but only with clear guardrails and a culture that keeps all product teams exploring new ideas.
  19. Healthy products show strength in usage growth, depth of engagement, and clear value moments.
  20. Win-loss analysis becomes meaningful when handled objectively by product marketing, supported by real data, and paired with a culture of curiosity from product teams.
About the speaker
Trisha Price Pendo, CPO Member
About the host
Sid Shaik Cloudera, Head of Product, Private Cloud Data Services

Sid is a seasoned Product Leader in the Data Platforms domain. At present, he runs Product at Cloudera for its fastest growing product line, Private Cloud Data Services. Prior to Cloudera, he co-founded a Silicon Valley startup-- Performance Sherpa; his company built performance engineering workflow automation for databases and middleware. Prior to those roles, he worked at Yahoo!, Qubole, Asterdata and Oracle in various Product and Engineering roles. As a Product Manager, Sid loves the creative process of discovering, defining and solving meaningful technology problems in large markets and enjoys scaling product businesses. In his down time, he enjoys taking his kids to soccer practice, he practices yoga, and advises startups.

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