Work With Dr. Shepherd

Four ways to work together.

I take on a limited number of engagements at any time. Each is structured differently, but all operate on the same principle: real accountability, real results.

Engagement 01

AI Governance
& Strategy

When the governance architecture is in place, your board can approve AI bets with real confidence — because the accountability structures, decision rights, and risk tiers are already working, not being built after something breaks. Most boards aren't there yet: they're approving investments without a clear model for who owns the outcomes or what level of oversight each initiative actually requires.

I help PE boards and portfolio company leadership teams build the governance architecture that makes AI a durable asset, not an audit risk. This work is grounded in the frameworks I developed across 25+ years of AI and product leadership — and published in The AI-Native Organization.

What you leave with

Board-level AI governance policy and decision rights framework

AI Readiness Index across leadership, data, process, risk, and board literacy

Trust tier classification for every AI initiative in your portfolio

Board reporting template for AI investment decisions and ROI measurement

90-day governance roadmap with clear ownership at each level

Engagement formats

How this engagement is structured

Most AI governance work runs 60–120 days for the initial framework, followed by an optional retainer for ongoing board advisory.

Board Advisory RetainerMonthly engagement. Ongoing governance advisory, board prep, AI literacy sessions.
Governance Assessment60-day project. AI Readiness Index + governance framework + board reporting structure.
Portfolio ScanFor PE firms. AI risk and readiness assessment across a portfolio of companies.
Engagement 02

PE Operating
Partnership

I've managed a $1.2B P&L at CDW, directed product strategy at Microsoft for Defense and Intelligence customers, and built and exited a company. When I embed with a PE-backed portfolio company, I'm not an advisor with a framework — I'm an operator with scar tissue.

Operating partnership engagements are structured around a specific value creation mandate. I work at the CPO, SVP, or GM level, typically with authority to hire, build, and make product and go-to-market decisions that move the thesis forward.

Where I drive value

Leadership infrastructure: roles, accountabilities, decision rights in first 60 days

Operating cadence design: the rhythm of reviews, reporting, and accountability forums

Product and platform strategy aligned to the investment thesis

AI integration and operating model redesign — not bolt-ons to legacy org charts

Exit readiness: building the bench and operational story 18 months before you need it

What to expect

How operating partnerships are structured

Engagements are typically 6–18 months. I work at the senior leadership level with real authority — not as an external consultant submitting decks.

Embedded Operating PartnerFull-time or near-full-time. Senior leadership role with a clear mandate and accountability.
Value Creation Sprint90–120 days. Focused engagement around a specific inflection point — launch, restructure, or pre-exit prep.
Board Operating PartnerPart-time. Board-level operating support alongside the portfolio company leadership team.
Engagement 03

Fractional CPO &
Interim Leadership

Sometimes a company is between senior leaders. Sometimes the business is moving too fast to wait for a full-time hire. Sometimes the board needs someone with the title and authority of a CPO or SVP but not the overhead of a full seat.

As a Fractional CPO, I step in with real operating authority — running the product and technology organization, setting direction, and building the team — while working on a timeline that's structured around your actual need, not a permanent hire.

When this makes sense

Bridge between departing CPO/CTO and permanent hire — keep momentum without losing ground

Scaling inflection: company is outgrowing its current product organization structure

M&A integration: acquired company needs senior product/tech leadership immediately

AI transformation: company needs a leader who can set the AI agenda and deliver it — not just advise on it

Board accountability: investors need a senior operator who reports directly and tells the truth

Structure & commitment

What a fractional engagement looks like in practice

Engagements typically run 90 days to 18 months, with a defined scope and clear success criteria established at the outset.

3–5 days per weekFor bridge situations and high-velocity engagements requiring near-full-time presence.
2 days per weekFor transformation and AI agenda engagements where deep thinking matters as much as presence.
Defined outcomesEvery engagement has a specific mandate. We agree on what success looks like before day one.
Engagement 04

Board Advisory &
Independent Director

Boards are approving AI investments, signing off on operating model changes, and overseeing leadership transitions — often without a director who has actually done any of those things at scale. The gap isn't intent. It's the absence of someone who can evaluate an AI thesis with the same rigor they bring to a financial model, and challenge an operating assumption before it becomes a missed target.

I bring the AI governance, operating model, and P&L experience that most boards are missing. Not as a subject-matter expert brought in for a single session — as a director with skin in the outcome. The practical difference: the board can approve bolder AI bets — and hold management accountable for them — because someone at the table has actually done it.

What this brings to a board

Independent evaluation of AI investment theses — governance readiness, execution risk, and value creation probability

Operating model challenge: the ability to stress-test whether the management team's plan will actually work

Technology-to-business translation — bridging the gap between what the CTO is reporting and what the board needs to decide

AI governance policy ownership at the board level, including decision rights, risk tiers, and accountability mapping

Pre-exit operating narrative: building the AI and product story that holds up in diligence

Engagement formats

How board advisory is structured

Board relationships are typically ongoing. I take on a small number at a time to maintain genuine engagement — not board seat collection.

Independent DirectorFormal board seat. Full director accountability with the AI, product, and operating model lens the board needs.
Board Observer / AdvisorOngoing retainer. Attends board meetings, reviews materials, and provides independent perspective without a formal seat.
Pre-Transaction AdvisoryDefined project. Preparing the board's AI and operating narrative for a fundraise, acquisition process, or major strategic decision.
How it works

Every engagement starts the same way.

Ready to start?

The discovery call is 30 minutes.
No pitch. Just a direct conversation.

Tell me what you're trying to solve. I'll tell you whether and how I can help — and if I can't, I'll tell you who can.