choose
Find the business opportunity worth the time. Ignore the rest for now.
David Sherry / AI strategy partner
AI strategyfor founder‑ledcompanies.
I partner directly with founders to decide where AI can create the most leverage, turn the right opportunities into working tools and workflows, and build the capability inside the team.
start with the AI roadmap
the problem
Don’t have time tobecome your company’sAI department?
You know AI could move the business forward. But between clients, the roadmap, and the team, deciding where to start keeps falling back to you.
Your team experiments when they can. Useful ideas stay half-built. The work that should get easier stays manual because no one owns the next step.
I help you choose the bottleneck worth fixing, turn it into a small build the team can finish, and develop someone inside the company to carry it forward.
the point of view / 01
Small companies have a massive tailwind if they turn repeatable work into software rails, while keeping human taste and judgment where it matters.
how the work moves
See it. Scope it. Ship it.
build
Make the smallest useful version with the people who will actually use it.
own
Teach someone inside the company to run, improve, and extend what gets built.
two ways to work together
Roadmap the first move. Build what matters.
AI–01focused starting point
AI roadmap
In one focused session, we map the opportunities, choose the one most worth pursuing, and turn it into a practical plan.
- Map the useful opportunities across the company
- Rank them by value, feasibility, and urgency
- Choose the first workflow and internal owner
- Leave with a practical 90-day plan
useful decision guaranteed.
roadmap the first move Leave knowing what to pursue now, what to consider later, and what not to spend time on, or I will refund the fee.
AI–02ongoing partnership
Strategic AI partnership
Ongoing support to prioritize opportunities, guide implementation, develop internal capability, and decide what should be built next.
- Work on one meaningful business priority at a time
- Scope the smallest useful version with the team
- Guide the internal owner as they build and test
- Measure what changed and decide what happens next
keep it moving.
build what matters If we continue within 14 days, the full Roadmap investment is credited.
your AI capability
Build with me. Own it without me.
I bring the outside perspective, judgment, and momentum. Someone inside your company builds and tests alongside me.
The goal is not to keep another consultant around forever. It is to make your team more capable every time we build something.
useful → used → owned
why david
Operator’s judgment. Advisor’s perspective.
I founded and bootstrapped Death to Stock, grew it to 500,000 subscribers, and eventually handed the reins to a new CEO. Today I work closely with founders to see what matters, turn priorities into action, and build companies that can keep moving.
2,200+founder sessions
50+founders advised
12years operating
“David became much more than a coach, a right-hand person who was part of the business. That’s really rare.”
Adrian Alfieri / CEO, Verbatim
ready when you are.
Where could AI help your company leap forward?
start a conversation I work closely with no more than five companies at a time.