Better Tech Leadership #149 Allan MacGregor: Building Smarter - The Evolution of AI and Software Engineering
Aug 19, 2025
Allan MacGregor, CTPO at Humi, discusses his role in aligning product and engineering teams for better collaboration. He sheds light on the latest advancements in artificial intelligence and the careful approach required for its integration, particularly in managing sensitive data. Allan also shares insights on navigating the unique challenges of building a fintech startup in Canada and the importance of strong leadership during workforce restructuring. His perspective on making contrarian decisions in tech reveals valuable strategies for balancing innovation with practicality.
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Accidental CTPO And Team Alignment
- Allan became an accidental CTPO after product leadership left and he merged product and engineering under one leader.
- That alignment led to engineers collaborating tightly with product and improved output despite a small team.
Small Team, High Expertise
- Humi keeps a compact engineering team with most engineers senior and acting as subject-matter experts.
- Deep domain knowledge in engineers can outperform sheer headcount for product success.
Delegate To Strong Functional Leads
- Delegate operational responsibilities to strong BPs so you can focus on strategy and cross-functional decisions.
- Trust leaders who operate their functions better than you to free time for higher-level work.
