Operator, not just advisor.
Keith Vertrees has built AI products, led engineering organizations, and made high-stakes product and technology decisions. RealWorldAI.Work brings that operator perspective to teams shipping AI pilots, offers, and operating-model changes.
IBM — Pillar A Credibility
Building AI before it was a strategy
Long before "enterprise AI strategy" became a boardroom agenda item, Keith was building it at IBM. As Director of Product within the Watson Marketing division, he led teams shipping AI-powered products to Fortune 500 clients — learning, firsthand, how large organizations actually absorb and operationalize machine learning capabilities.
That work included designing and delivering immersive AI demonstration experiences for IBM Customer Experience Centers across multiple cities — gesture-based, narrative-driven environments that showed Fortune 500 executives what AI could do for their marketing organizations. These weren't demos built by a slide deck; they were fully functional prototypes that won budget, changed roadmaps, and generated patents.
The IBM years built a deep foundation: how enterprise AI adoption actually fails (misalignment between product and engineering), how it succeeds (leadership conviction plus practitioner execution), and what separates a compelling proof-of-concept from a product that ships and sustains.
Shift Technologies — Pillar C Credibility
Operating with real stakes
As SVP CTO/CPO at Shift Technologies, Keith held full P&L responsibility for the product and engineering organization at a publicly traded automotive marketplace. The title wasn't ceremonial — it meant making decisions on headcount, architecture, and roadmap with real board visibility and real consequences.
During that tenure, Keith led M&A integrations that restructured entire engineering orgs, navigated nine-figure financial decisions, and rebuilt product development culture in a company scaling under pressure. He managed the tension between investor expectations, engineering reality, and customer demand — the exact triangle that breaks most technology transformations.
That experience is what makes the RealWorldAI.Work advisory model different. The recommendations aren't drawn from frameworks developed in a consulting lab — they're drawn from having been the person in the room when the board wants answers, engineering wants more time, and customers want now.
Current Work — FDE Credibility
Still in the arena
Keith isn't advising from the sidelines. Today, he is embedded as a Fractional CTO/CPO inside enterprise B2B SaaS companies, working in the codebase, sitting in the sprint reviews, and making the architectural calls that move products forward. The engagements are long enough to see outcomes, not just deliver reports.
The technical work is current. Keith builds production AI workflows with Claude Code and vLLM, runs inference workloads on a DGX Spark and RTX 5090, and operates at the practitioner level where most advisors stop at PowerPoint. When a client asks whether a particular architecture will scale or whether an AI feature is actually production-ready, the answer comes from someone who built it this week — not from a whitepaper.
That combination — operator experience at scale, plus daily hands-on AI engineering — is the foundation of every RealWorldAI.Work engagement. It's what makes it possible to compress timelines, avoid the expensive mistakes, and give clients the unvarnished assessment they need rather than the optimistic one they might prefer.
What makes us different
Proprietary Methodology
The AI-First Enterprise Framework is a structured blueprint for deciding where to start, what to pilot, and how to turn early AI wins into repeatable operating changes.
Operator, Not Just Advisor
Former CPTO who has made these decisions with real budget, real headcount, and real board pressure. This is practitioner-led transformation, not consultant theater.
Technical Depth
Runs AI workloads on production-grade hardware, builds with Claude Code and vLLM daily, and understands the engineering reality at the practitioner level. No hand-waving.
What clients say
“Your quick impact and ability to constructively challenge our thinking has been invaluable. The detailed feedback and strategic insights are helping us navigate complex challenges and get to the best answers for our AI initiatives.”
Senior Executive
Product & Engineering Leadership
Enterprise B2B SaaS
“Keith brought exceptional technical leadership during a critical infrastructure transformation. His ability to optimize performance while managing complex migrations kept our platform running smoothly for our users.”
Mohit Kadahari
Co-founder
Sprect
“The AI demo was truly impressive — showing how AI can revolutionize marketing workflows. A game-changer for the industry.”
Marketing Executive
Enterprise Client
Fortune 500 Company
Ready to work with an operator?
Book a discovery call to discuss where you are in your AI transformation journey, or take the assessment to get a structured view of your readiness.