Derek Wise, CPTO at Civica, discusses leadership, legacy tech, and the art of failing fast

In this episode, Lucas Hendrich sits down with Derek Wise, CPTO at Civica, to discuss the role of technology leadership, blending product and engineering functions, and navigating the complexities of modern software development.

Here’s a recap of their discussion:

1. Leadership and Team Building: Derek emphasizes building a culture where teams feel safe to fail and learn from mistakes. He hires people who are better at their jobs than he is, fostering a high-performing environment.

2. Integrating Acquired Teams: Merging teams isn’t just about plugging in APIs. It requires negotiation, deciding who owns what, and understanding the customer value each team delivers.

3. Legacy Tech and Innovation: Successful monoliths are often the hardest to change. Derek highlights the tension between innovation and business risk, stressing the importance of documenting decisions to understand past choices.

4. Distance from the Customer: The speed of change correlates with how close a team is to the customer. Gaming allows rapid iteration, while healthcare demands caution due to regulatory constraints.

5. AI and Tech Debt: AI tools like GitHub Copilot are helping engineers manage technical debt by optimizing code and suggesting improvements, freeing teams to focus on innovation.

6. Communicating with Investors: Whether in VC or private equity-backed companies, Derek translates complex tech concepts into business impact, aligning engineering efforts with revenue and customer outcomes.

7. Managing Younger Talent: The new generation values autonomy and purpose. Derek adapts his leadership style to provide freedom while setting mechanisms for teams to demonstrate progress and learn.

8. Personal Growth and Well-Being: Inspired by the book Why We Sleep by Matthew Walker, Derek restructured his habits to prioritize rest, leading to better decision-making, creativity, and empathy.

Derek's insights reveal that while the tools and industries change, the core principles of leadership, customer focus, and continuous learning remain universal. Tune in for a conversation packed with practical wisdom for technology leaders navigating an evolving landscape.

Stay tuned for more conversations with industry leaders as we explore the intersection of technology, business, and innovation.