PodcastNovember 26, 2025
Software Leaders UNCENSORED: From engineer to CTO across four industries.
A frank conversation with Steve Taplin on the patterns that traveled across financial services, luxury retail, media, and legal tech — and what changes (and what doesn't) when you become CTO.
By Jimi Li
A long-form, candid conversation about a career arc that crosses four industries and the patterns that travel — what reads as engineering judgment, what reads as commercial instinct, and where the two meet.
What we cover
- The four-industry path. GE Capital → L'Oréal → Coach → News Corp → ALM. Lessons each one taught and the ones that only show up the second time around.
- Engineer to executive. What changes in the daily work, where the new failure modes are, and how to keep your hands close enough to the work to stay credible.
- Building leadership teams that absorb AI. Hiring profiles, fusion teams, the right pace of change — and the signals that say you're moving too fast or too slow.
- PE-owned tech leadership. The conversations that happen every Tuesday in a PE-owned company that don't happen elsewhere, and how that reshapes the CTO role.
- The next twelve months. Where Jimi expects the operating model of enterprise software companies to land — and what the smart leaders are already doing about it.