CEOs, COOs and operators at privately held $30M-$500M companies who have AI on the 2027 agenda and no answer yet for where it fits. We wrote it first for leaders in the Carolinas. You don’t need to be technical, and chapter 13 defines every term we use.

Nothing. Tell us where to send it and the PDF lands in your inbox.

Why do you ask about revenue, ownership and location?

It tells us who’s reading, so the note from Drew and the next edition fit your company. Everyone who asks gets the playbook, whatever they answer.

Will I see client names or numbers in it?

No. The patterns come from our 2026 meetings with leadership teams, operators and partners. There are no client names or client numbers in it.

Can we run the leadership session without you?

Yes. Chapter 04 has the agenda, the survey and the templates to run the half day yourself. If you’d like help, reply to the email and we’ll set up time.

How is this different from the AI North Star Playbook?

The AI North Star Playbook was written for technology leaders. This one builds on it and is written for the CEO and COO who own the 2027 budget.

Yes. We’re treating it as a product and will keep updating it as AI changes. Email hi@stealthx.co if there’s something you’d like to see in the next version.

2027 AI Strategy Playbook · free

Decide where AI fits in your 2027 plan, and put a number on it

A free 55-page playbook for CEOs, COOs and operators at privately held $30M-$500M companies. It’s how we plan AI with leadership teams, written down so you can run it yourself.

See where your company stands before you spend, with a 12-point self-check.
Build a budget you can defend with your own numbers: four cost lines and a value case for every AI bet.
Run a half-day leadership session that ends with owners and dates. The agenda, survey and templates are included.
Leave with a one-page AI plan for your 2027 budget and a checklist for the first 90 days.

Cover of the StealthX 2027 AI Strategy Playbook

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Read a few pages before you sign up

These are real pages from the PDF, exactly as they print. The rest of the playbook comes with your copy.

Contents

Fourteen chapters, in the order you’ll use them

Start with where you stand, then find the money, run the leadership session, write the one-page plan and get through the first 90 days. Use cases, trust checks, common concerns, an FAQ and a glossary round it out.

Playbook page 5: the table of contents listing chapters 01 to 14 with page numbers.

Chapter 02

Where you stand

Two ladders, one for a single person and one for the whole team, and a 12-point self-assessment across one person at a time, the whole team and leadership. Your score tells you which chapter to start with.

Playbook page 10: the two ladders table, single player and multiplayer, rungs 1 to 5.

Playbook page 11: the 12-statement self-assessment checklist and the table for reading your score.

Chapter 07

Use cases paying off in the mid-market

Each use case names the problem, what the AI does, the human step, what it needs first and how you’ll know it’s working. This page covers orders that arrive by email and quoting from your own job history.

Playbook page 36: two operations use cases, orders that arrive by email and quoting and pricing from your own history.

Chapter 08

Keep people in the loop

AI drafts, a person approves, and each workflow earns more room on its own record. The chapter ends with an eight-point trust design checklist to run before anything goes live.

Playbook page 40: the eight-item trust design checklist to run before a workflow goes live.

Get the full playbook

What’s inside

Fourteen chapters. The ones marked preview are on this page, and the rest come with your copy.

01
Start here
Why 2027 is the budget year, and eight guiding principles.
In your copy
02
Where you stand
Two ladders and a 12-point self-assessment.
Preview
03
Find the money
Four cost lines and a value case for every AI bet.
In your copy
04
Run the half-day leadership session, with or without us
The agenda, the survey and the templates.
In your copy
05
One-page AI plan for your 2027 budget
The page you bring to your board or owners.
In your copy
06
The first 90 days
A 30/60/90 checklist for getting started.
In your copy
07
Use cases paying off in the mid-market
Back-office and customer-facing work, with the human step named.
Preview
08
Keep people in the loop
How to design trust in, plus the checklist.
Preview
09
Common concerns
The worries that come up in most rooms, answered.
In your copy
10
Applying this in your industry
Where the first bets differ by industry.
In your copy
11
FAQ
Ten questions leadership teams ask, starting with what to budget.
In your copy
12
About the author
Who wrote it and how to reach him.
In your copy
13
Glossary of terms
Plain definitions for every term we use.
In your copy
14
AI transformation story
One story, blended from several engagements, start to finish.
In your copy

About the author

Drew Burdick

Founder & Managing Partner, StealthX

Drew has spent over 15 years designing products and experiences and advising executives at Fortune 500s, mid-sized companies and startups. He’s helped many companies decide where AI fits and quickly build working prototypes that test what creates business value.

Connect with Drew on LinkedIn