What kinds of organizations does Paul Cheek advise?

Paul advises boards and C-suites at F500 / mid-cap / high-growth companies, PE operating partners ($500M–$5B AUM), and growth-stage founders ($5M–$150M revenue). Engagements focus on AI strategy, governance, organizational design, and transformation roadmaps.

What engagement models does Paul offer?

Three models: (1) Board advisor — formal seat, 2–4 days/quarter; (2) Project sprint — 8 to 12 weeks with a defined deliverable; (3) Executive coaching — two 60-minute sessions per month for senior leaders. All engagements are Paul direct, no junior team.

How is Paul Cheek different from other AI advisors?

Paul is an operator first — he has built five software companies and is currently founding new ones. He brings practical expertise via the AIDE Institute's AI maturity research, no junior team, no vendor incentives, and no retainer without conviction.

Will Paul disclose conflicts of interest?

Yes. Paul advises a number of AI companies; if a conflict could arise, he provides a clear disclosure before any recommendation.

Strategic advisory

Strategic counsel for the AI era.

Paul works with boards, C-suites, and founders who need to move fast on AI without guessing. He brings practical expertise and the hard-won judgment of an operator who is still building.

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Who I work with

Three types of engagement. One standard of rigor.

Boards and C-suites

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.

PE operating partners

$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.

Founders and CEOs

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

Four areas. All grounded in current practice.

AI Strategy Development

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.

Enterprise AI Transformation

End-to-end support for organizations restructuring their operating model around AI capability. Covers organizational design, governance, tooling decisions, talent strategy, and implementation sequencing.

Innovation Leadership

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.

Executive AI Education

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

Three ways to engage. All start with a conversation.

Ongoing

Senior advisor

A standing senior advisory relationship. Paul is available for time-sensitive calls and provides independent perspective on major AI decisions.

Time commitment2 to 4 days per quarter

Best fitCompanies that need an independent AI voice at the table and want Paul's network and research access year-round.

Time-bound

Project sprint

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.

Time commitment8 to 12 weeks, structured

Best fitOrganizations that need to move fast on a specific decision and want a deliverable they can act on, not a report that sits on a shelf.

Flexible

Executive coaching

A monthly sounding-board relationship for senior leaders navigating complex AI decisions. Two sessions per month, no deliverables required. Pure strategic dialogue.

Time commitmentTwo 60-minute sessions per month

Best fitCEOs, Chief AI Officers, and board chairs who want a trusted, independent thinking partner with no conflict of interest.

What makes this different

An operator who is still operating.

Most AI advisors are former executives or career consultants. Paul is currently building companies, teaching the next generation of founders at MIT, and running research through AIDE Institute. The advice comes from current practice.

I am an operator first. I have built five software companies. The work I advise on is the work I do.

MIT keeps me at the frontier. AIDE Institute runs the most rigorous AI maturity research in the market. I bring both into every engagement.

No junior team. Every engagement is Paul directly or the people he trusts most. Only experts.

No retainer without conviction. I only engage where I believe I can move the needle. If I am not the right fit, I will tell you and point you to someone who is.

Independent.* I have no incentive to recommend a particular vendor, platform, or approach. My only incentive is your outcome.

* I advise a number of AI companies so should one of them arise in conversation or recommendations a clear disclosure will be made.

Ways I create value

Beyond the strategy deck.

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

Where the real decisions get made.

For larger engagements

Need a full team behind it?

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.

Visit Cheek LLC →

Ready to talk?

Share a few lines about your situation. If there is a fit, Paul will respond within one business day.

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