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My guest today is Bobby Tahir, a highly experienced CTO and technology executive with a track record of building, scaling, and modernizing engineering organizations in high-growth and private equity–backed companies.

In this conversation, we unpack what really changes for a CTO the moment private equity enters the picture: the shift in expectations, the compressed timelines for value creation, and the strategic mistakes that can quietly derail even strong technical leaders. Bobby shares what PE-backed CTOs often underestimate, and what the best ones do differently when the pressure is on.

We also dig into how AI is reshaping the CTO role in very real ways. Not the hype, but how it actually changes where a CTO spends their time, which teams feel the impact most, and where productivity gains are truly showing up versus being oversold.

And finally, we get into people leadership, specifically the hard realities of leading distributed and outsourced engineering teams across cultures and geographies. Bobby offers a grounded take on what great leadership looks like today when teams may never share the same room, but standards still can’t slip.

If you’re a CTO, a technical leader, or anyone navigating scale under pressure, this one’s for you.

Bobby, thank you so much for being here!

151. Bobby Tahir. On CTOs, PEs, AI, and Outsourcing.