Strategic advisory
Paul works with boards, C-suites, and founders who need to move fast on AI without guessing. He brings deep expertise and the hard-won judgment of an operator who is still building.
Schedule a consultationOutcomes
Mid-cap, large-cap, or mega-cap — every advisory engagement starts with a specific, measurable outcome the work can be held accountable to. Pick the one that maps to where you actually are. Numbers below are placeholders for your scale.
01
Make XX% of our team AI-literate
02
Help X,000 employees each build their first AI agent
03
Teach X,000 employees to create autonomous actions for the organization
04
Scare the s*** out of my board of directors so they learn about AI, invest in AI, or recruit AI talent to the board
05
Inspire my leadership team with the art of the possible with AI
06
Inspire all XX,000 people leaders in my company to build AI leverage for the organization
07
Transform my organization's operating model to be AI-native
08
Build one AI agent/workflow live for my team
09
Accelerate our AI risk/compliance/governance processes by X%
Featured feedback
On behalf of the [Confidential Company] team, a huge thank you for what was an incredible 2 day learning experience for our leadership team. It is super rare to get this group together (and live in person) for what was a thought provoking and energising two days.
Paul — Your presentation was outstanding. Many positive remarks from the [Confidential Company] team throughout the day… one of the comments I overheard was, “I thought we were ahead in AI, but after hearing Paul I understand now we’re way behind.”
Wow and thank you!! You were amazing today. The insights, the experiential feel, the fun delivery. I consider today a gift to me to have our paths cross. We are excited to have more of you — should your agenda allow…
Who I work with
F500, mid-cap, and high-growth companies
Enterprise leadership teams facing the AI mandate without an internal playbook. Paul brings a board-ready framework, a diagnostic for where you actually sit on the AI maturity curve, and a 12 to 24-month governance structure.
Typical outcome
A clear AI strategy that your board can hold the exec team accountable to.
$500M to $5B AUM
Private equity firms that need to assess AI maturity across a portfolio and build AI capability at the operating company level. Paul advises on both the portfolio strategy and the company-level transformation, often working directly with management teams.
Typical outcome
Portfolio-wide AI maturity assessment and a standardized playbook for operating company deployment.
Growth-stage companies, $5M to $150M revenue
Founders who need a strategic sparring partner on AI architecture, product strategy, and how to restructure the organization before a raise or exit. Paul has built five software companies. He does not advise on theory.
Typical outcome
A clear operating model for AI and a roadmap to the next phase of the company.
How I help
A structured process to define your AI vision, prioritize your AI portfolio, and create a board-ready roadmap with KPIs. Includes an AI maturity diagnostic and a gap analysis against where you need to be in 24 months.
End-to-end support for organizations restructuring their operating model around AI capability. Covers organizational design, governance, tooling decisions, talent strategy, and implementation sequencing.
For organizations that need to build an internal innovation capability without spinning out a skunkworks that the core business will kill. Grounded in the Disciplined Entrepreneurship methodology and the Startup Tactics framework, adapted for corporate environments.
Custom education programs for board members, C-suites, and senior leadership teams. Designed to build shared language and decision-making frameworks, not just awareness. Typically delivered as a series of half-day workshops.
Engagement models
A standing senior advisory relationship. Paul is available for time-sensitive calls and provides independent perspective on major AI decisions.
An intensive 8 to 12-week engagement with a defined output: AI strategy, governance framework, organizational design, or transformation roadmap. Paul works directly with your team, not through a junior consultant.
A monthly sounding-board relationship for senior leaders navigating complex AI decisions. Two sessions per month, no deliverables required. Pure strategic dialogue.
Ways I create value
Here are some of the ways I have created value for the companies I advise:
Led AI transformation initiatives
Made intro to new board member
Recruited a head of sales
Intros to key contacts for international expansion
Provided thought leadership to executive team
Presented at sales conferences and on webinars
Made connections to relevant researchers and research centers at MIT
Hosted daily calls during a frustrating fundraise
In the room
For larger engagements
For transformation engagements that require a team, Paul's firm Cheek LLC delivers strategy, governance, training, and implementation with a dedicated group of practitioners. Same rigor, broader capacity.
Share a few lines about your situation. If there is a fit, Paul will respond within one business day.
Schedule a consultation