Lessons from Merging Eng Teams and Becoming CTO

In this episode of Tech Teams Today, we sit down with Lloyd Hsu, CTO at Roofstock, to break down the real challenges of post-merger engineering, org design, and the personal leap from SVP of Engineering to CTO.

Inside the episode:
- Why keeping codebases separate after a merger sets you up for failure
- The cultural landmines that slow down org integration
- How infrastructure and security blind spots grow with your team
- The difference between leading delivery and leading strategy
- Why AI tools (like Cursor, Windsurf, Copilot) need human oversight

Chapters
00:00 Intro — Who is Lloyd Hsu?
01:13 The hidden cost of merging engineering teams
03:05 Culture clashes: The hardest part of M&A
05:04 Combining processes without losing momentum
08:41 The assumptions Lloyd got wrong post-merger
11:31 Patterns across biotech, proptech, and SaaS
13:47 Balancing speed, scale & security
21:47 Applying AI to products and platforms
24:09 Why AI tools need technical judgment
26:02 Measuring AI adoption (or not)
28:46 Managing distributed teams globally
31:48 Why engineering culture is a multiplier
35:47 Building long-term careers, not short-term output
40:01 Lightning Round
45:54 Final thoughts + leadership takeaways