From Truck Driver to AI Builder: Cristino Santiago on Career Pivots and Learning by Doing

Cristino Santiago went from pre-med to trucking to cybersecurity to Lean Portfolio Management. He shares how he learns anything new, the AI tool he built to do his timesheet, and why you don’t need to code to start with AI. What if your next career move meant a step back first? In this episode of AI-Powered Career Edge, Yousuf talks with Cristino “Chris” Santiago, a Lean Portfolio Manager with one of the most varied career paths we’ve covered. Chris started pre-med, then became an over-the-road truck driver who drove to every state in the lower 48. After that came tech support, student support programs, and a run of low-paid internships in AI, crypto, and cybersecurity. Those internships led to a full-time job as a cybersecurity software engineer, and later a move into product and program management. In this conversation: Why Cris took $8-10/hour internships when he was earning more as a trucker His four-step learning process: learn it, do it, write about it, teach it A real AI project: an MCP that logs his FreshBooks timesheet for him What an MCP is, in plain language Why the next challenge for AI is value realization, not just AI training Why domain experts are well placed to succeed with AI His advice: invest in yourself, start now, and be okay with failing Key quote “You already have all the knowledge that you need. You just need to know how AI can help you solve problems now.” About the guest Cristino “Cris” Santiago is a Lean Portfolio Manager working in transportation consulting. His background spans DOD contracting, cybersecurity software engineering, and teaching Python at a UCF boot camp. Chapters 00:00 Intro 01:21 Chris’s career arc 05:08 Why he took internships to learn 09:08 How Chris learns 11:31 Screen share: AI projects 15:50 What is an MCP? 20:25 What’s next: AI value realization 22:48 Advice for getting started with AI 25:22 Domain experts and AI Next step Not sure how AI fits into your career? Take the free AI Career Gap Analysis: https://aicareergapanalysis.edge-careers.com/ai-career-gap-analysis-page AI, career change, career pivot, MCP, no-code AI, lean portfolio management, cybersecurity, lifelong learning