Two pathways. Three altitudes. One clear line.
How the work is structured, who I work with inside the company, and where the line sits between strategy and execution.
The Advisory Project
For a specific strategic moment, your capital raise, category launch, repositioning, brand architecture or GTM reset. Embedded with you and your executive team for the duration of the project, with weekly working sessions and async support between.
You leave with the strategic decisions made, alignment across your executive team, and a written plan your team can execute against.
A Series B-stage AI company three months out from a raise. Six weeks. Investor narrative sharpened, category claim defined, positioning system that holds under VC pressure.
A scaleup CEO with a head of marketing who knows what to do but no clear strategic direction. Five weeks. Positioning reset, GTM model redesigned, marketing team given the brief they've been waiting for.
The Advisory Retainer
Ingrained in your business as a standing senior voice. Weekly strategic time with you. Working sessions with your executive team. Standing presence in your board moments where narrative, category or growth architecture is on the table.
The kind of relationship where the advisor knows the business well enough to be useful in the moment a decision needs to be made, not just at the scheduled meeting. Most retained clients say the value is having Simon's number on speed-dial when something happens.
An AI-health company through an 18-month period of international expansion. Weekly time with the CEO. Standing presence in board meetings where positioning, hiring decisions, M&A messaging or investor narrative is on the table. Quarterly half-day with the executive team on strategic priorities.
Most engagements begin with a short scoping conversation. If we're aligned, we move directly to a project or retainer.
If we're not, you'll leave with a sharper read on the problem and a recommendation for someone better suited.
A compressed format for teams who need senior thinking now.
For founders and executive teams who need structured strategic work, without committing to a multi-week engagement.
The same thinking from the advisory practice, delivered in a compressed, working format. Built around a specific decision your team needs to make in the next 90 days: a category claim, a narrative reset, an investor positioning sprint, a GTM model rebuild, or a pre-raise board strategy session.
Often used as the entry point to longer advisory work, and sometimes the only engagement a team needs.
Bringing your team together for an offsite, board strategy session, or founder cohort? Most workshops are scoped in a 20-minute call.
A small number of workshops each quarter, alongside the advisory practice. Founder cohort programs from 2026.
The AI-Native Growth Intensive
A 1–2 day executive masterclass for marketing, growth and operations leaders rebuilding the function for the next era. Drawn from the forthcoming book. Built around four working sessions: the AI-native marketing function blueprint, the new growth architecture, category claim under AI conditions, and the operating model that compounds. Delivered privately for one company, or quarterly as a curated cohort of 8–12 leaders from non-competing companies.
Executive team intensive
One to two days with your founder and executive team. Working format, not talking format. Designed around a specific strategic decision you need to make, often used pre-raise, pre-launch or pre-reposition. Delivered in person at your offices or off-site.
Board strategy session
Half-day or full-day session with your founder, executive team and board. Built around an inflection moment, a raise, a category claim, a major repositioning, or an M&A conversation. The format boards remember.
Founder cohort workshop
Two-day workshop for 8–12 founders going through the same strategic moment. Curated cohort. Hosted format. Built around narrative, category and AI-native growth architecture. Run quarterly from 2026.
Three altitudes. One coordinated engagement.
The CEO is the buyer and strategic partner. The executive team is where the work gets built day-to-day. The board is where strategic output gets presented. Senior advisory only works when all three altitudes are coordinated.
With the CEO
Strategic partnerFraming the problem, setting direction, owning the outcome. Strategic alignment on positioning, category, narrative and growth. Kickoff, midpoint, final, ad-hoc strategic calls.
With the executive team
Working partnerHead of marketing, head of growth, head of operations, COO. Weekly working sessions, side-by-side collaboration. They bring inside knowledge of the company. I bring senior outside perspective.
With the board
Strategic counselBoard narrative, investor narrative, presenting positioning to investors when the moment requires it. Standing presence in board meetings during raises or strategic inflection points.
For heads of marketing, growth and operations:
I work alongside you, not over you. The strategic clarity from this work makes your job easier, not harder, sharper direction from above, clearer permission to execute below. Strong functional leaders are partners in this work, not subjects of it.
Strategy and senior decisions are inside the work. Execution and team management are outside. Zero grey area.
What I advise on and help decide.
- Narrative and positioning strategy
- Category design and architecture
- Growth architecture and GTM model
- Capital raise and investor narrative
- Brand strategy and architecture
- Founder and executive positioning
- Board and investor communication
I produce the strategic artifacts that come out of these decisions, positioning documents, narrative frameworks, GTM maps, investor narratives. These are outputs of the work, not the work itself.
What I don't do.
- Campaign management
- Media buying or performance marketing
- Content production or copywriting
- PR or social media execution
- Agency briefing or production management
- Day-to-day marketing operations
- Team management or hiring
If you need execution capacity, you need an agency or a head of marketing. The strategic clarity from this work makes both work better.
I work with marketing teams, not over them.
Strong functional leaders are partners in this work. The best engagements I've had were ones where the head of marketing or growth was an active co-author of the strategy.
Senior or not at all.
I work directly with founders, CEOs and their executive teams. Senior strategic work requires senior access.
Decisions, not deliverables.
The value of senior advisory is the conviction in the room when the decision gets made. Deliverables are a byproduct.
Honest, not flattering.
The reason founders pay for outside counsel is to hear what their team may not say. I'll tell you what I think, including when I think you're wrong.
Two to three companies at a time.
The practice exists to be useful inside specific companies, not to scale across many.
Book a call.
A 30-minute conversation about where you are, what you're trying to build, and whether this is the right fit for senior counsel on what comes next.
Not sure which fits? Start with a general scoping call →
Open to two new advisory partners this quarter. Workshops by invitation.