AI Strategy & Roadmaps
Connect AI investments to business decisions, portfolio priorities, measurable outcomes, and responsible adoption — sequenced so each phase funds the next.
Solutions Overview
Most AI programs stall at the pilot. I help executive teams get past it.
Advisory for leadership teams that need an AI roadmap tied to real decisions — with the governance, sequencing, and investment narrative to survive contact with the board.
The situation
Why AI programs stall
Most enterprises are not short on AI activity. They are short on AI decisions — the small number of consequential choices that would turn scattered experimentation into operating advantage. Four patterns show up almost every time.
01
The portfolio is organized around technology, not decisions
Initiatives are named after models, tools, and vendors. Nobody can point to the business decisions that would get faster, clearer, or more defensible if the work succeeded.
02
Pilots have no path to production
Promising proofs of concept never acquire an owner, a budget line, or an operating model. The demo lands; the transition to something that runs the business never gets designed.
03
Governance arrives last
Data, risk, and responsible-adoption questions surface after commitments are made — and stop the work at the most expensive possible moment.
04
There is no shared executive vocabulary
The board hears capability, the operators hear disruption, and finance hears cost. Teams are deciding against different pictures of the same program.
The leadership imperative isn't to start with technology. It's to start with the decisions that move the business — and then build the AI capability that makes those decisions faster, clearer, and defensible.
Skip Vanderburg
Decisions named
The AI portfolio maps to a short list of business decisions, each with an owner.
Roadmap sequenced
Work is ordered by value, feasibility, and risk — with an investment narrative attached.
Governance in place
Data, risk, and responsible-use guardrails are designed in, not retrofitted at review.
Where I add value
Six solution areas
Advisory grounded in building the thing, not just recommending it — across the operator, consultant, and founder seats.
Agentic Decision Intelligence
Design multi-agent approaches that synthesize evidence, compare scenarios, and improve executive decision velocity rather than adding another dashboard.
Enterprise Transformation
Align technology, operating models, customer experience, and cross-functional teams around change that scales past the first business unit.
Product & Platform Leadership
Convert emerging-technology concepts into enterprise SaaS capabilities, working prototypes, and market-ready solutions with a credible delivery path.
Innovation & Experience Design
Apply human-centered design and emerging technology to create differentiated products and services people actually adopt.
Board & C-Suite Communication
Translate complex AI concepts into clear choices, risks, governance priorities, and an investment narrative the board can act on.
How the work is prioritized
Opportunities are ranked with established frameworks rather than intuition — RICE, MoSCoW, Eisenhower, scenario planning, risk assessment, and resource optimization — so the roadmap can be defended line by line to finance, risk, and the board.
How we work together
Three ways to engage
Scoped to the decision in front of you — from a single executive session to ongoing advisory alongside your leadership team.
A working session with your leadership team to establish a shared, non-hype view of what AI can and cannot do in your operating context — and where the real constraint sits.
- Current-state read on the AI efforts already underway
- Where decisions — not tools — are the bottleneck
- A short list of candidate opportunities, ranked
- Written summary the team can circulate internally
A defined engagement that produces an AI roadmap tied to business decisions, prioritized with established frameworks rather than intuition, and sequenced against real capacity.
- Opportunity assessment and prioritization across the portfolio
- Operating model and governance guardrails
- Sequenced roadmap with investment narrative and success measures
- Board-ready readout and executive summary
Retained advisory alongside your executive team — the senior AI perspective in the room, without adding a full-time role or a consulting bench.
- Standing counsel to the CEO, CIO, CTO, or CPO
- Portfolio and vendor decision support ahead of commitments
- Board-ready communication and narrative
- Working sessions with the teams doing the delivery
Engagements are typically sized after a short scoping conversation; the briefing is often the fastest way to establish whether a sprint or a retained relationship is the right next step. Travel and expenses billed at cost.
Focus sectors
Where this work lands hardest
The advisory approach is industry-agnostic, but five sectors carry the combination of decision complexity, regulatory weight, and data fragmentation where getting past the pilot matters most.
Insurance
Carriers & brokers
Underwriting, claims, and distribution each run their own experiments. The portfolio view — what to fund, in what order, against which loss-ratio outcome — is missing.
Opening move · A single prioritized roadmap across underwriting, claims, and service, with a governance layer above it.
Healthcare
Providers & payers
Clinical and administrative AI advance on separate tracks, and governance questions — privacy, clinical accountability, model oversight — arrive after the pilot has already been promised.
Opening move · Separate the decisions that carry clinical risk from the ones that don't, and sequence accordingly.
Financial Services
Banking & capital markets
Model risk management and regulatory expectation set the pace, and ambitious AI programs stall waiting for a defensible control story.
Opening move · Build the governance and evidence trail into the roadmap rather than bolting it on at review.
High Tech
Software & platforms
No shortage of capability — the constraint is prioritization. Too many credible AI bets, too little agreement on which ones earn engineering capacity this year.
Opening move · Rank the portfolio with explicit frameworks so the trade-offs are visible and arguable.
Manufacturing & Industrial
Operations & supply chain
Operational data is abundant and fragmented; AI initiatives cluster at the plant level and rarely aggregate into an enterprise capability.
Opening move · Identify the recurring enterprise decisions the plant data should be feeding, and build toward those.
Sector framing is a starting point, not a template. Every engagement begins with your operating context, the AI work already in flight, and the decisions your leadership team is actually trying to get right.
Background
Built across the operator, consultant, and founder seats
Thirty-five years translating emerging technology into enterprise strategy, products, customer experiences, and operating advantage — at Fortune 500 companies, global consultancies, enterprise software firms, and as a founder building the thing itself.
35+
Years across Fortune 500, global consultancies, and enterprise software
17
Beta customers validating agentic decision intelligence at Prioriti AI
3
Published books on generative AI, decision intelligence, and prioritization
15
Podcast episodes on enterprise AI implementation and ethics
Selected experience
- Prioriti AI — Founder & CEO; agentic decision intelligence and generative prioritization
- Brillio Design Studio — Head of Design
- Tata Consultancy Services — Partner; Chief Innovation Officer, DESS
- Siebel Systems & Mercury — Executive technology and innovation roles
- The Coca-Cola Company — Engineering and development leadership
Writing & thought leadership
- Illuminating Pathways — decision intelligence and generative AI for enterprise prioritization (2024)
- The Future of Generative AI: Creating Tomorrow
- The Rise of Decision Intelligence
- Executive speaker, Practical Journey to AI; featured expert, The Catalyst by Softchoice
- Creator and host, Illuminating Pathways podcast
Let's talk
What decision are you trying to get right?
If your team is weighing where to invest in AI — or trying to move from pilots to something that actually runs the business — a short conversation is usually the fastest way to find out whether I can help.
LinkedIn
/in/skipvanderburg
Based in
San Francisco Bay Area
