Citi

Bosch

Morgan Stanley

Raythe Technologies

Bristol Myers Squibb

Prolego

30 years in enterprise AI; dozens of Fortune 500 engagements; 1,000+ execs trained

Beta cohort: Participants get additional bespoke guidance & are expected to offer course feedback.

Beta

Cohort 1

In two weeks, turn chaotic AI activity into clear priorities, defensible decisions, and a plan for getting organizational alignment.

Enterprise GenAI Execution Operator

Kevin Dewalt

Three decades building enterprise AI — from neural nets to GenAI

Headlines make it sound like GenAI transformation is solved: agents deployed, workflows automated, ROI unlocked.Inside real enterprises, it isn’t.<ul><li>The board expects measurable impact</li><li>Your peers expect acceleration</li><li>Your teams expect clarity</li></ul>Meanwhile, vendor demos multiply, pilots stall in proof-of-concept limbo, and new AI capabilities outpace your company's ability to absorb change, creating portfolio sprawl, fragmented investments, and stalled adoption.If that’s your company, you’re not lacking ambition. You’re lacking a disciplined execution system.After leading dozens of seven-figure GenAI engagements at Fortune 500 companies, I codified a repeatable framework for triaging GenAI portfolios.In this two-week private intensive — limited to 10 senior executives — I will teach you how to apply this framework to your own program and you will leave with a defensible 90-day execution plan to gain control of your GenAI portfolio, including:<ul><li>GenAI Portfolio Map (stop / scale / start)</li><li>AI Tools Adoption Plan (usage + change)</li><li>Vendor Evaluation Framework (selection gates)</li><li>Company-Specific Production-Ready Build Plans (owners + milestones)</li><li>Templates and Decision Prompts</li><li>Private 1:1 Plan Review</li></ul>

For senior leaders accountable for GenAI results amid portfolio sprawl

Take command inside your unique enterprise constraints

Bring your full AI portfolio into a single operating view

Turn tool enthusiasm into adoption that delivers results

Put buy-versus-build decisions on a disciplined footing

Concentrate build effort where it can drive the highest returns

Turn fragmented initiatives into a 90-day execution plan

You control or directly influence priorities and budget, and can deploy resources.

Authority over GenAI funding and resource allocation

You have projects or tools underway. The challenge is focus and delivery, not getting started.

GenAI work already in motion

You can lead cross functional change and make tradeoffs, so we focus on GenAI program execution and adoption.

Senior strategic experience

Executives accountable for GenAI results at $50M+ enterprises You must set priorities, align leaders, and deliver measurable outcomes.

Rising leaders preparing to run GenAI programs You want a structured way to focus, align, and execute before the stakes rise.

Context Files: Scale GenAI Across Complex Work

Learn why durable context improves AI work far beyond one-off chat prompts.

Understand core shift behind context files

Create your own repeatable workflow with only Microsoft Word + an LLM

Build your first context file in 10 minutes

Prepare to extend this pattern to multiple projects and complex enterprise work.

Design a scalable reasoning system

Double Your Team's GenAI Adoption (Without Training)

Build a simple prompt and email that gets your team using GenAI on real work this week.

Immediately Accelerate GenAI Usage

Use a focused assignment that works for skeptics and power users at the same time.

Create Adoption Without Another Program

Generate a summary that reveals themes, blockers, and the fastest path to scaled adoption.

Prolego turns scattered AI motion into an executable plan

Prolego

About Prolego

Courses

The GenAI Execution Framework: A Two-Week Intensive for Senior Executives

Lightning Lessons

Context Files: Scale GenAI Across Complex Work

Double Your Team's GenAI Adoption (Without Training)