What does it actually look like when a CIO walks into a 20-year-old technology organization and turns it AI-first in under 12 months — without shutting anything down? In Part 3 of the Sage Tech series on Ten Thousand Miles, Vic Pepe sits down with Corey Kirspel, a transformational CIO in the healthcare technology space. This is not theory. This is a boots-on-the-ground account of one of the most compelling enterprise modernization stories in the AI era. Corey walked into a private equity portfolio company three years into a five-year hold — facing a 12-million-line legacy code base, a $2M cost reduction mandate, tribal knowledge locked inside a handful of people, and a board demanding an AI-first strategy. Here is what happened next. What you'll learn: * Why Claude, Copilot, and Cursor weren't enough alone — and what Corey layered on top * How Sage Tech mapped 12 million lines of legacy code in 48 hours — architecture, vulnerabilities, and evergreen documentation included * The one-engineer experiment that turned skeptics into believers — a five-month project done in six weeks * How $1.2M in annual infrastructure savings was unlocked in three months without a ground-up rewrite * The SDLC operating model shift that took a team from 100 lines of code per day to 10,000 * What the first 90 days of AI transformation actually looks like — and how to justify the ROI fast Whether you are a CIO, CTO, PE operating partner, or business leader trying to move from talking about AI to executing it — this episode is required listening. Chapters: 00:00 — Welcome and guest introduction 02:00 — The CIO's real job in the AI era 03:53 — Walking into a PE portco with a 20-year-old code base 05:25 — Why Claude, Cursor, and Copilot weren't enough alone 08:15 — Discovering Sage Tech and the virtual architect model 12:04 — Breaking free from tribal knowledge and key-man dependency 19:34 — The product leader who thought she knew her own system 22:04 — The one-engineer experiment that changed everything 33:49 — From one engineer to eight Scrum teams — the rollout strategy 42:01 — First 90 days and a message for anyone still waiting Connect: * Sage Tech AI: https://www.sage-tech.ai * Subscribe for new episodes every week Keywords: enterprise AI transformation, CIO strategy, legacy code modernization, AI-first enterprise, Sage Tech AI, software modernization, technical debt, private equity portco, healthcare technology, SDLC AI integration, CIO podcast, technology leadership, AI tools for developers, code base analysis, digital transformation ROI
