AI Transformation Sprint

"Your AI pilot worked. Leadership bought in. Now nothing has changed."

Get an AI adoption maturity assessment, a change management plan, and a leadership alignment package — before the ROI questions get harder to answer.

70-person org Copilot standardization + agentic practices rolled out at Best Buy
3 months Structured AI bakeoff before committing to enterprise standard
Value Flywheel Direct participant — first cloud platform and organizational change at Liberty Mutual
Fortune 50 AI transformation from the inside, not a slide deck

The stalled AI rollout problem nobody on the leadership team wants to name

Every executive I've talked to has a version of the same story: the pilot worked. Leadership got aligned. Tools were licensed. Announcements were made. Six months later, nothing has fundamentally changed. Teams are working the same way they were before the AI initiative. The tools are licensed but underused. The ROI projections that justified the investment are now questions at the quarterly business review you don't have clean answers to.

This isn't a technology problem. It's a change management problem — and most organizations treat it like an IT rollout.

What's actually happening

  • Tools are licensed and available but adoption is 20% of what was projected
  • No one owns the rollout — it's on the roadmap for five different teams
  • Individual champions are using AI effectively; the rest of the org isn't
  • There's no measurement model connecting AI use to business outcomes
  • Leadership alignment from the pilot has eroded — different executives have different answers about what success looks like

The risk if this keeps drifting

  • Board and CFO AI ROI questions get harder to answer every quarter
  • Cynicism builds in the org: "remember when we were going to transform with AI?"
  • High performers who don't see organizational support for AI tools start looking elsewhere
  • A new wave of AI tools arrives and you still haven't operationalized the last round
  • The window to lead this transformation closes — and someone else becomes the model

A clear picture of where the org actually is — and a plan with real owners and real milestones.

The sprint ends with four deliverables your leadership team can use immediately. What you receive is the foundation and the plan. Executing the rollout is on your team — by design. The organizations that lead on AI adoption own it internally. This sprint gives you everything you need to own it.

What you receive at the end of weeks 4–6

  • AI adoption maturity assessment: Where the org actually is vs. where it thinks it is — by team, function, and tool. Includes current adoption rates, friction points, and the gap between executive expectations and on-the-ground reality.
  • Change management plan: Named owners, sequenced milestones, success metrics, and a realistic timeline. Scoped to what your organization can execute, not what looks good on a slide.
  • Leadership alignment package: Executive narrative, CTO/CHRO/CDO talking points, and board-ready framing that gets leadership speaking with one voice about the AI program.
  • Rollout playbook: A tool-specific adoption plan tied to the AI investments you've already made. Identifies quick wins, removes blockers, and sequences adoption for minimum disruption.

What this doesn't include: Executing the rollout. The sprint delivers the assessment, the plan, and the playbook. Your team implements them. This boundary is intentional — the engagement is scoped to what I can validate and deliver in 4–6 weeks with direct access to your leadership and data.

Engagement Terms

4–6 week fixed scope  ·  Fixed price  ·  No retainer required

Scoped to organization size and AI program maturity. Includes direct engagement with CHRO, CDO, or CTO and the functional leads responsible for AI adoption. Most clients use the deliverables to reset internal alignment, restart a stalled rollout, or build the case for continued investment.

Four to six weeks. Structured. No surprises.

01

Week 1 — Maturity Assessment

Diagnostic interviews with the leadership team and functional leads. Adoption survey across teams currently using AI tools. Honest inventory of where the org is — including what leadership believes vs. what's actually happening.

02

Week 2 — Gap Analysis

Map the distance between current adoption and stated goals. Identify the specific friction points blocking adoption: skills gaps, tool access, leadership misalignment, measurement gaps, or cultural resistance. Quantify the gap where possible.

03

Weeks 3–4 — Plan Development

Change management plan and rollout playbook built against the real gaps identified. Leadership alignment package drafted. Ownership assigned for every milestone. Plan reviewed with key leads before finalization.

04

Weeks 5–6 — Readout & Handoff

Executive readout with the leadership team. Final deliverables handed off. 30-day quick-start actions identified so your team can move immediately after the engagement ends.

Led from the inside at Best Buy and Liberty Mutual

70-person org

Enterprise-wide Copilot standardization · Agentic development practices

At Best Buy, I didn't just recommend an AI standard — I designed and ran the process that got to one. A 3-month structured evaluation of competing tools, a data-driven recommendation to the CTO, and then the harder work: rolling out agentic development practices across a 70-person global engineering organization across two continents. The technical decision took three months. Getting teams to actually change how they work took longer and mattered more.

Earlier in my career, at Liberty Mutual, I was a direct participant in what later became the Value Flywheel — setting up the first cloud platform and navigating the organizational change that comes with moving an enterprise off decades of infrastructure assumptions. That work was documented in The Value Flywheel Effect as a model for how technology transformation actually happens at scale. The lesson wasn't the technology. It was that someone had to own the change.

Both experiences share the same lesson: the technology works. The adoption doesn't happen by itself.

What I learned from leading these transformations

  • AI tools outperform expectations when adoption is actively managed — they underperform when it isn't
  • The gap between "tool available" and "team using it effectively" doesn't close on its own
  • Organizations that succeed treat AI adoption like a product launch, not an IT rollout
  • Leadership alignment at the start saves months of confusion at the execution layer
  • Measurement matters from day one — "teams are using it more" is not a metric

What I see in stalled AI programs

  • Most organizations are further behind on adoption than leadership believes
  • The most common gap is not technical — it's accountability and named ownership
  • Change management for AI rollouts gets deprioritized because it's harder to measure than licensing
  • The fastest path to results is structured adoption of tools already licensed, not new tools
  • Executives who stay close to adoption metrics in the first 90 days get dramatically better outcomes

If the ROI questions are getting harder to answer, the window is still open — but not indefinitely

A 20-minute call will tell us both whether there's a fit. No commitment required.

Schedule a 20-Minute Call