Enterprise GenAI Execution Operator

Headlines make it sound like GenAI transformation is solved: agents deployed, workflows automated, ROI unlocked.
Inside real enterprises, it isn’t.
The board expects measurable impact
Your peers expect acceleration
Your teams expect clarity
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:
GenAI Portfolio Map (stop / scale / start)
AI Tools Adoption Plan (usage + change)
Vendor Evaluation Framework (selection gates)
Company-Specific Production-Ready Build Plans (owners + milestones)
Templates and Decision Prompts
Private 1:1 Plan Review
In two weeks, turn chaotic AI activity into clear priorities, defensible decisions, and a plan for getting organizational alignment.
Ground decisions in mandate, constraints, and risk before inherited motion sets your agenda.
Sequence decisions so competing activity does not dictate what happens next.
Lead with command over tradeoffs, ownership, and next moves under real pressure.
Simplify decision-making with a single portfolio view of the key GenAI dimensions: tools, vendors, local workflows, and internal builds.
Separate durable progress from pilot churn, scattered effort, and work that does not deserve your attention.
Surface blockers and adoption reality while the portfolio is still yours to shape.
Move the conversation from tool preference to operating behavior tied to business results.
Identify which usage patterns can spread and back repeatable workflow change instead of scattered power-user wins.
Turn scattered experimentation into a managed adoption effort with ownership, evidence, and follow-through.
Judge vendor options on fit, burden, durability, and evidence before flashy demos take over the discussion.
Make realistic, disciplined calls based on SME demand, internal effort, and operating load.
Establish a standard that lets you say yes, no, not yet, or pause without reopening debates.
Separate promising ideas from the few opportunities that justify real build commitment.
Only make build investments when there is a credible path to production impact.
Stop teams from sinking time and goodwill into work that creates motion but does not ship.
Sequence work in one plan instead of wasting another cycle of discussion without commitment.
Ensure your decisions can clear governance, funding, and ownership friction in the business.
Leave with defensible next moves, explicit tradeoffs, and a plan you can execute.

Three decades building enterprise AI — from neural nets to GenAI
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.
You control or directly influence priorities and budget, and can deploy resources.
You have projects or tools underway. The challenge is focus and delivery, not getting started.
You can lead cross functional change and make tradeoffs, so we focus on GenAI program execution and adoption.

Live sessions
Learn directly from Kevin Dewalt in a real-time, interactive format.
Organizational Snapshot: your current actionable diagnosis
I share the framing I use to get leaders out of vague AI ambition and into a diagnosis they can use immediately to focus decisions, reset expectations, and stop reacting to scattered activity. You get a leadership-ready brief that captures your mandate, constraints, risks, and where execution is breaking down.
Current State Map: your single operating view
I give you the framework I use to surface your full portfolio fast, so you can see where efforts overlap, where ownership is unclear, and what no longer deserves leadership time. You quickly create a working map of what is already in motion across tools, vendor activity, team-configured workflows, and internal builds.
Tool Adoption Plan: a way past low adoption and random enthusiasm
I provide the logic, examples, and measures I use to separate valuable operating use of AI from random activity. I’ll demo the activation approach I use when leadership wants ROI (not more ineffective training). You leave with a practical plan to achieve org-wide change that can produce measurable impact.
Buy-vs-Build Decisions: a standard for making realistic technical calls
I share my practical decision logic for judging whether a capability should be bought, built, paused, or left as it. Logic that will hold up once execution begins, that reflects your strategy, and factors in your real operating load.
Vendor Evaluations: a process to protect your agenda from shiny new demos
I give you my vendor evaluation framework which covers evidence, durability, reliability, SME demand, and operating burden. It covers the hard questions that usually get skipped when teams get pulled in by polished demos. You’ll be able to use it to force clarity before a pilot becomes a commitment the business is not prepared to support.
Build Strategy: where to invest, and how to avoid expensive distractions
I share how to separate what should be lightweight local experimentation from the few opportunities that deserve real technical build resourcing. I bring the criteria and examples I use to keep leaders from treating every promising idea as a portfolio bet.
Agentic Workflow Strategy: help business teams create value without chaos
I share how to spot the simple, bounded AI workflow opportunities business teams can configure themselves, and where they should not. We cover failure modes, ownership, and reliability guardrails so local experimentation creates value without becoming a support burden or scaling mess.
Build Investment Criteria: a standard for what can be reliably delivered
I share the operating standard that I use to tell the difference between a project that can ship and one headed for prototype purgatory. You’ll use it to stop weak builds early, before they can consume your precious technical resources and goodwill.
1:1 Review of Your 90-Day Plan: live, constructive pressure-testing
We’ll do a one-on-one review of your 90-day execution plan, focused on whether the sequencing, tradeoffs, ownership, and near-term moves will hold up inside your business. I pressure-test the plan with you directly, so you leave with something you’re able to defend with complete confidence.
Private Executive Q&A: candid discussion with peers under similar constraints
I facilitate a private discussion space anchored in real enterprise mandates, not generic AI commentary. We’ll use this time to surface the hardest practical questions around sequencing, funding logic, and governance friction. You’ll gain perspective from other executives, identify patterns and sharpen your judgment.
Maven Guarantee
This course is backed by the Maven Guarantee. Students are eligible for a full refund up until the halfway point of the course.
5 lessons • 2 projects
Live sessions
4 hrs / week
9 hours of interactive time across 2 weeks, used to discover, discuss, decide in an exec working group led by Kevin.
Projects
2 hrs / week
Real work time used to prepare your GenAI Program capstone: a bespoke 90-day execution plan.
Kevin helped our executives turn GenAI from a vague idea into clear business action. I’ve been attending and hosting his executive workshops for nearly 20 years, and most recently he helped lead several Scott Data cohorts involving 15 companies.
Executives came in with lots of ideas but little clarity on what GenAI meant for their business. Kevin made it concrete. He walked them through real use cases, showed what was possible, and helped them decide what to do next. The feedback was consistently strong. Some teams moved ahead with broader tool adoption. Others used the work to shape board-level strategy.

Ken Moreano
Kevin helped our leadership team turn AI from a loose set of ideas into a practical plan for 2026. I organized and ran this workshop for 20 senior leaders across the business, and for many of them it was the first time AI really clicked in a business context.
Kevin made it concrete. He showed where tools could improve day-to-day work, where we should look for team-level automation, how to spot real AI workflow opportunities, and when to buy versus build. The result was better alignment across the leadership team and a much clearer foundation for budgeting, adoption, and next steps going into the year.

Katelyn Viola
$10,000
USD