Advisor
$1,500/ per month
Up to 3 hours per month
A trusted second brain for the calls you can't make alone.
- Monthly 90-minute strategy session
- Async Slack — reviewed periodically, replies between sessions
- One written decision memo each month
Fractional Chief Strategy Officer · Dan Jahn
Strategic Leadership for the AI Era
See the vision. Find the clarity. Build the strategy.
A fractional Chief Strategy Officer for founders and executives — with the AI and technology fluency most advisors don't bring.
The Vision → Clarity → Strategy Framework
One framework for every high-stakes decision.
The hardest calls aren't solved by a template. They're solved by three moves, in order — the logic behind how I work with founders and leadership teams.
Vision
What future are we building, and why does it matter?
Before tactics, we get sharp on where you're going and why it's worth the cost — a vision that survives contact with the market, not a slogan for the wall.
Clarity
What's true, what's confusing, what's misaligned, and what must be decided?
We separate signal from noise, surface where the leadership team is quietly misaligned, and name the decisions that can't keep waiting.
Strategy
What choices, systems, and priorities will move the organization forward?
Then the moves: the priorities, trade-offs, and operating systems that turn vision into action — and a way to keep deciding as the ground shifts.
Strategic thinking
Companies grow when their choices are aligned, intentional, and rooted in a strategy that actually matches the market. A Fractional CSO provides executive-level strategic leadership without the full-time cost — bringing clarity to complex decisions, integrating AI and emerging technology into how your business actually works, applying a global lens to decisions that cross markets, cultures, and borders, and helping leadership teams move faster with confidence.
Track record
$0M
Value created
0%
Return client rate
0+
Projects delivered
About
Three decades. Seven books. One operator.
I’m Dan Jahn — a strategist, advisor, and operator who has spent more than three decades helping founders and senior executives grow with clarity, discipline, and direction. I’ve built companies across technology, creative, and education sectors; taught leadership and strategy at major universities; advised organizations from early-stage startups to established enterprises; and worked in environments ranging from the White House to Silicon Valley.
My lens is global. Born in Sri Lanka, raised in Europe, and having worked across more than 68 countries — with degrees in International Relations and Religious Studies — I learned early that people, institutions, and markets don't all think alike. When a decision crosses cultures, borders, or belief systems, I read the forces underneath it: trust, authority, incentives, history, and power. That's the difference between a strategy that works on paper and one that holds up in the real world.
Technology and AI strategy run through almost every engagement I take. I help leaders make sense of generative AI, automation, and the broader digital reshaping of their industry — separating signal from hype, and translating it into clear decisions about what to build, what to buy, and where to invest.
My background gives me a wide-angle view of how leaders think, how teams succeed, and where companies get stuck. That perspective runs through everything I do, including my books on leadership and strategy — Leading with Impact and Stop Waiting Start Coaching, with The Human Algorithm, Stop Following, and The Mindful Executive on the way in 2026 — alongside earlier books on belief systems and conflict, The Pacem Papers and Islam in Sudan, which together distill practical lessons for leaders navigating complexity across cultures.
The pattern is the point. Builder, teacher, author, and global strategist isn't a résumé of hats — it's one way of reading people, markets, and decisions under pressure. When the stakes are high and the situation is genuinely complex — culture, capital, technology, and competing interests at once — that range is what lets me see the move others miss.
As a fractional CSO, I help founders and C-suite leaders sharpen strategic focus, build scalable systems, and integrate emerging technology into the business. Whether you’re entering a new growth phase, facing organizational challenges, or preparing for a pivotal shift, I bring the strategic rigor, AI and technology fluency, cross-industry insight, and operational clarity to move your company forward with speed and intention.
The work
I help leaders make better strategic decisions when the stakes are high and the situation is complex — with the judgment, range, and rigor to move forward with confidence.
As featured in
Testimonials
In their words.
invaluable
“Dan has advised us on everything from marketing to strategic to computers to VOIP to websites to e-commerce and everything in between. He is an invaluable partner for us.”
Casey Prather
Director, RMAC
guidance
“Clear, practical advice that actually made sense. Exactly the guidance we needed to move forward with confidence.”
Matt Hines
Digital Content Director, Sitka Gear
manageable
“The way Dan breaks down complex decisions makes everything feel manageable, and our team finally aligned.”
Gabby Roberts
Marketing Director, JILS
clarity
“Calm, structured, with deep technology insights — every session brought clarity we could act on right away.”
Kirk Conner
CFO, EPRD
braintrust
“Dan is a braintrust of information spanning AI, digital marketing, and modern business strategy.”
Lauren Guillory
Founder, Vow & Paper
decisive
“Dan turns a tangle of options into a decision you can actually defend. Every conversation moves us forward instead of in circles.”
Jim Bernier
Principal, JEBSys Associates
sharp
“He sees the second- and third-order effects the rest of us miss, then makes them simple enough to act on. Sharp, fast, and never academic.”
Steve Stewart
CEO, Protogenic
rigorous
“Dan brings real rigor to capital decisions — pressure-testing both the numbers and the story behind them. We allocate with far more conviction now.”
Dan Haskin
Managing Partner, Haskinvestments
clarifying
“I came in with noise and left with a plan. Dan has a gift for cutting to what matters and giving you the language to rally a team around it.”
Polly Babcock
Operations Director, SHOWLABS
grounded
“Dan brings perspective you can't get from inside the business, and the candor to tell you what you actually need to hear. Every conversation leaves us sharper.”
Sharon Steadman
Founder, The Steadman Group
Where the work matters most
Strategic leadership for complex decisions.
Some decisions can't be solved by a template. They take judgment, pattern recognition, cultural awareness, technological fluency, and the ability to align people around a clear path forward.
- Founder-led growth
- AI strategy & implementation
- International expansion
- Cross-cultural strategy
- Strategic planning
- Leadership alignment
- Market positioning
- Organizational complexity
- Capital & resource allocation
- Conflict-sensitive decisions
How I help
Five engagements, one through-line: better strategic decisions when the stakes are high.
Strategic Outcomes
What the work produces.
Engagements are confidential, so these are categories, not case studies — the kind of result leadership teams bring me in to create.
Aligned founder and executive teams around a single growth strategy
Built AI-enabled operating systems for growing companies
Designed investor-facing strategy and roadmap architecture
Clarified positioning and category strategy in crowded markets
Advised on cross-cultural and international strategic decisions
Built scalable decision frameworks for complex organizations
How an engagement runs
Same rhythm at every tier. The depth changes; the cadence doesn't.
Strategy work fails when it's a quarterly off-site and then silence. This is the operating rhythm I run with every client — from the founder on Advisor to the leadership team on Fractional CSO.
Week 1
Strategic audit
A 90-minute working session covering your current bets, near-term decisions, and where the leadership team is unaligned. I take notes; you don't have to.
Week 2
Memo + 90-day plan
A written memo with the priority calls and a 90-day operating cadence. Not a deck — a doc you can forward to your board.
Monthly
Memo + working sessions
One written strategy memo each month. One or two live sessions on whatever's loudest. Async Slack in between — answers come within hours, not days.
Quarterly
Scenario refresh + offsite prep
Three scenarios (base, upside, downside), five key drivers, one decision rule per scenario. If you're running an offsite, I'll prep the agenda and the materials with you.
Where the work lives
- Slack — async decisions, daily access
- Cal — sessions scheduled in your timezone
- Shared workspace — memos, scenarios, decision log
Engagement tiers
Choose the depth of partnership your moment calls for.
Three-month minimum commitment on monthly tiers.
Most chosen
Strategist
$4,500/ per month
Up to 10 hours per month
Recurring strategic rigor for growing companies that need direction, prioritization, and execution clarity.
- Two working sessions per month
- Quarterly scenario refresh + key driver review
- Monthly priority memo for the leadership team
- Async Slack — actively monitored, with frequent replies
Partner
$9,000/ per month
Up to 22 hours per month
For leadership teams managing multiple initiatives, growth decisions, and operating complexity.
- Weekly leadership working session
- Quarterly off-site facilitation + readout
- Board prep support each quarter
- Direct involvement in 1-2 priority initiatives
Fractional CSO
$15,000/ per month
Up to 40 hours per month
Embedded senior strategy leadership without hiring a full-time executive.
- In your operating cadence — weekly and ad hoc
- Strategy memo + scenario model owned by me
- Board narrative + investor-deck rigor
- Strategic hire input + interview rounds
Not sure yet?
Or, simply by the hour
On-Demand
$500/ per hour
A single high-leverage decision, a rapid second opinion, or one tightly-scoped conversation. No commitment, no monthly retainer — book the hour you need.
Questions you’re probably asking
The honest answers before you book.
A Fractional Chief Strategy Officer gives founders and leadership teams senior strategic leadership part-time — setting priorities, pressure-testing the big bets, integrating AI and technology, and turning vision into an executable strategy — without the cost of a full-time executive hire. In practice, it's an embedded second brain for the decisions that matter most.
Still something on your mind? Email me directly and I’ll reply within the business day.
Start the conversation
Most companies don’t fail from lack of effort. They fail from unclear decisions.
Twenty minutes. You leave with one specific strategic recommendation — including how AI and emerging technology fit into the next twelve months — regardless of whether we work together.