Chief AI Commercial Officer & Fractional CRO
Whether you're selling an AI product or adapting to how B2B buyers now evaluate - the gap is commercial, not technical.
Who I Work With
The CAICO engagement is designed for both. The entry point and approach differ - but both close the same gap.
R&D has outpaced commercial readiness. The product is real - but the revenue motion, messaging, and ICP were often built for a different buyer than the one you're actually winning. Every month without a working GTM is runway burned.
89% of B2B buyers now use AI extensively before they contact a vendor. They arrive shortlisted. Your reps are showing up late to conversations where the evaluation is already complete - visible as pipeline softening, longer cycles, and reps arriving after the decision is made.
About Dave
I help established and scaling companies build the commercial leadership and revenue infrastructure they need to grow - and to navigate the disruption that AI is bringing to every market, including theirs. The bottleneck is almost never the technology. Value is unlocked in the people, process, and day-to-day execution.
What separates me from other fractional CROs is a career spent across multiple major technology disruption cycles - PC adoption, e-learning, SaaS, HR technology, and now AI - each time in a senior commercial or co-founding role, each time at the same inflection point organizations face now.
My most recent senior operating role was as EVP Global Sales at Insights Learning & Development - a $130M professional services business operating across 11 countries. I built and ran the commercial organization: 175 people, partner channels, direct sales, alliances, pricing, and revenue operations. I delivered 28% average annual growth at 21% profitability for two consecutive years. Clients included Google, Microsoft, Novo-Nordisk, BP, Sanofi and 100+ global enterprises.
I co-founded SightGlass Group - a research-based AI workforce readiness diagnostic platform - and I serve as CEO of Reset Productivity, the exclusive North American licensee. SightGlass is one of the tools I bring to CAICO engagements where the commercial challenge is tied to organizational readiness.
"The barrier to creating value through technology is always human, never the technology itself. I have spent 30 years proving it - in startups and larger organizations."
Dave is a creative and tenacious man with unlimited energy to meet business goals. His business drive is outstanding, but getting to know Dave on a personal level will really show you the true gentleman he is.
Dave is an exceptional thinker - creative, future-focused, innovative yet practical. He has a keen sense for identifying market opportunities and knowing the right risks to take. His terrific people skills, customer orientation, and fabulous sense of humor set him apart.
Four Engagement Types
Each engagement is structured for a specific kind of problem. I take a small number of clients at a time - which means when we engage, you have my full attention.
Bridges AI technology capability and commercial execution. For companies where the CEO knows the AI opportunity but cannot translate it into commercial traction - whether selling AI or adapting the commercial team to how AI-enabled buyers now evaluate vendors.
Start HereGTM redesign, ICP refinement, sales motion build, pricing architecture, and messaging - scoped, timeboxed, and accountable to a clear outcome. Built for AI companies whose go-to-market has not kept pace with their product. Converts to retained CAICO.
Fast ImpactRetained commercial leadership - owns revenue strategy, pipeline governance, team performance, pricing architecture, and GTM execution. Board-facing from day one. The operating partner who builds the machine, not just advises on it.
Most CommonStrategic input, network access, investor preparation, and commercial governance oversight. For established private companies and growth-stage businesses that want senior commercial judgment at the board level without the full-time overhead.
SelectiveProof of Work
These numbers come from a single sustained engagement - EVP Global Sales at Insights Learning & Development - not a career average. Two consecutive fiscal years, same P&L, same team.
Sustained across two consecutive fiscal years on a $130M P&L while maintaining 21% profitability. Both numbers held simultaneously.
Raised average NRR to ~115% while improving enterprise retention by 22%. Revenue that compounds inside the existing client base.
Achieved over two years through governance, QBR cadence, and tooling. Forecast accuracy is a proxy for the health of a commercial system.
Built as AI venture co-founder, validating 35 enterprise AI readiness engagements across three geographies.
Across 11 countries, operating under one unified commercial architecture built for complex, consultative, relationship-driven enterprise B2B.
One unified commercial architecture spanning direct sales, partner channels, alliances, pricing, and revenue operations.
Many CAICO engagements begin with a SightGlass diagnostic - a research-backed tool that measures whether an organization's people, culture, and structure are ready to generate value from AI before deploying it at scale. I co-founded SightGlass Group; Reset Productivity holds the exclusive North American license.
Start the Conversation
Tell me what is not working commercially. I'll tell you honestly whether it's something I can help with - and if it isn't, I'll tell you that too. No wasted time on either side.
AI companies (Series A-C) whose product is working but whose go-to-market, messaging, or revenue motion has not kept pace.
Established $15M-$80M B2B companies - professional services, L&D, HR tech, consulting - whose buyers have moved to AI-first evaluation and whose commercial team is still running the old playbook.
PE and VC operating partners - if the AI commercial challenge is live at a portfolio company, I welcome an introduction directly.
412-526-1593 · Charlotte, NC
Thanks for reaching out. I read every message personally and will reply within 24 hours. — Dave