David Klein
For OpenAI

I help leadership teams see
what’s newly possible with AI –
then decide what to do about it.

That has been the through-line of my career: McKinsey-trained and Wharton-educated, I’m a former founder and CEO who shipped with engineers for a decade, who now leads hands-on AI transformation for CEOs and executive teams. This is what I do.

View résumé See the match
The match

What you’re looking for – I’ve done it.

Six of the things your post asks for. I’ve done them.

Innovation & strategy with CEOs You’ve led innovation, strategy, or transformation work with CEOs and senior leaders.
Since ChatGPT 3.5 launched, I’ve been engaged by boards and CEOs to reposition their operating models for the AI era – embedding with leadership, mapping where AI creates advantage versus exposure, and turning it into a plan they act on. Before that: founder/CEO, McKinsey, and Chief of Staff to the #3 executive at American Express.
Workshop design & facilitation You can move a group from possibility to decision.
I design and run the executive sessions that force hard and necessary choices. After a recent full-day Executive Team offsite I led: the CEO said it was “phenomenal,” and his key lieutenant (the key operational lynchpin at the company) called it the “best offsite I’ve ever been a part of.”
Reframe, don’t just optimize You help leaders rethink a familiar problem, not just improve a process.
My instinct is to reframe. For a client recently, I re-cut their CRM data across thousands of implementations to help them discover their #1 growth problem was not “win rate” but lead-to-opportunity conversion – changing where they invest.
Structure without narrowing You bring structure to ambiguity without closing down the opportunity too soon.
McKinsey-trained and founder-tested: turning the meandering into the clear is my craft – I was selected to McKinsey’s Global Faculty to teach it. As a founder I built a company in a category that didn’t exist – I know how to hold ambiguity long enough for opportunity to emerge.
Challenge leaders, keep trust You challenge senior leaders while keeping trust – imagination with rigor, not innovation theater.
I’ve spent my career in the room with executives – as a consultant, a chief of staff, and a CEO myself. And now as a senior counselor and advisor to CEOs and executive teams. I can push a leadership team hard on its assumptions and keep the trust. I know the difference between real change and innovation theater.
Fluent with technical teams You collaborate with engineers without being one, and make ideas tangible.
I shipped products with engineers for a decade and build with AI every day – agents, connectors, APIs. I’m not an engineer, but I speak the language, and I use working prototypes to test ideas.
Case study: a real engagement

From a fuzzy AI mandate to a clear path.

Recent work. Client details anonymized.

Software & services · AI-era transformation

Their core business was being disrupted by AI. They did not know what to do about it. They brought me in.

The situation
A software-services firm with a few hundred clients watched AI start to erode the work it sold. The brief was wide open: figure out what AI means for us, and what we should do.
Executive discovery
Embedded with the CEO and leadership team. Interviewed each leader, learned the business and its economics, mapped where AI created advantage and challenge – and surfaced the assumptions no one had said out loud.
The offsite
Designed and facilitated a full-day executive offsite that moved the team from open-ended possibility to a shared, three-part plan. We developed tactical ways to (1) fix the core growth engine, (2) use AI to cut the delivery cost, and (3) use AI to grow the value delivered to clients – all within a strategy we were able to pressure-test and align on live.
The organizational unlock
To accomplish these things, we designed a repeatable “innovation loop” – an operating model that turns delivery data and frontline sales signal into new AI-enabled offerings the team can design, test, and ship – continuously.
How I’d run it

How I take a leadership team from ambiguity to action.

The arc I run, whatever the industry. Tuned to each engagement.

Get inside the business – and the disagreements

“We know AI matters. We don’t agree on what it means for us.”

What I do
Interview the CEO and each senior leader. Learn the business, the customers, and the economics. Map where AI creates advantage versus exposure – and surface the assumptions no one has said out loud.
What leaders get
A shared, honest picture of where they actually stand, and the real disagreements worth resolving in the room.
The trap I avoid
Jumping to use cases before I understand the business. The best opportunities are usually hiding in the disagreements, not the obvious wins.

Turn a vague mandate into the questions that matter

“What do we do about AI?” is too big to answer. What are we really deciding?

What I do
Reframe the ambiguity into a small set of sharp innovation questions – the ones that, if answered, change where the company invests. Structure, without narrowing the opportunity too soon.
What leaders get
A focused agenda for the session: the handful of choices that actually move the business, instead of a hundred scattered ideas.
Why it works
I turn the meandering into the clear – I was selected by McKinsey’s Global Training Faculty to teach it to McKinsey professionals.

Run the room from possibility to decision

Plenty of ideas on the table, but no decision the team will commit to.

What I do
Design and facilitate the executive session. Push the team to think bigger than today’s processes, then force the trade-offs and drive to real choices.
What leaders get
Alignment they own, not a consultant’s recommendation they nod at. Decisions, not a deck.
Proof
A recent full-day Executive Team offsite: the CEO called it “phenomenal,” and his key deputy called it “best offsite I’ve ever been a part of.”

Make the future concrete enough to judge

“Sounds compelling. But would it actually work – and would customers want it?”

What I do
Guide a small tiger team to run tests on the strongest ideas – grounded in real feasibility.
What leaders get
Something they can react to and test – so the decision rests on evidence, not slideware.
Why it works
A decade shipping products with engineers, plus daily hands-on work with frontier models, agents, and APIs – so tangible means tangible.

Leave them with a portfolio, not a to-do list

“Where do we place our chips – and what happens Monday?”

What I do
Shape the choices into an opportunity portfolio: near-term experiments, bigger bets, and what each requires across operating model, governance, and technical feasibility.
What leaders get
A clear innovation direction, a roadmap of experiments, and the reusable method to keep doing this without me.
Why it matters
The goal isn’t one good workshop. It’s a repeatable motion the organization can run on its own.

How I run an engagement, tuned to each client – illustrative of the arc, not a fixed script.

Why this work, why now

The work I love, at the moment it matters most.

This sits where technology meets a leadership team’s hardest questions – the intersection I’ve operated at my whole career, as a consultant, a founder, and an advisor. I love it. It’s what I’m trained for and good at – it energizes me.

AI has hit its inflection point, and the leaders who move now will define their industries. Helping them see what’s newly possible – and turn it into action – from inside the company building the frontier is about as good as it gets.

Prepared independently by David Klein. This is a personal candidacy page and is not affiliated with, endorsed by, or sponsored by OpenAI.

© 2026 David Klein