Executive AI coaching

Turn an all-day task into a 45-minute one.

You build the AI that does it, one-on-one, in your first 2-hour session.

Executive AI coaching for business owners and leaders. Every session ends with a working tool you keep.

How it works · 73 sec
Book a free 30-minute call

Coaching from $9,000 · full pricing below

Client results

The job that used to take a day, gone.

Every number is the client’s own. Two of them happened in the first session.

First session
A full day45 minutes

Ben was pulling aircraft data and building market reports by hand. One session later, a full market analysis finished before lunch.

What would have taken me an entire day took 45 minutes.
Ben McPeak President, Vertical Jet Sales
First session
18 months of failureFirst try

After $100K+ on AI consultants, Scott still couldn’t pull structured data from 250-page curriculum guides. One session found the approach.

Eighteen months of failed attempts, and we solved it on the first try.
Scott Desimone Co-Founder, Really Great Reading
One hour
20+ dev-team hours1 hour

Deven arrived with a broken prototype. He left with a production-ready MVP, Stripe integration included, and knew how it worked.

He fixed everything while teaching me how it actually works.
Deven Delarco Founder, Gadgitmatic
Two sessions
2–3 hours per motionAutomated

A solo family-law attorney. AI now drafts every motion, complaint, and discovery she files, and she reviews instead of writes.

I have AI drafting skills for every motion, complaint, and discovery I write.
Sarina Gianna Founder, S. Gianna Law
Book a free 30-minute call

Coaching from $9,000 · full pricing below

How it works

No curriculum. No slides. You share your screen, I guide, you drive.

01

A 30-minute call Free

You tell me what takes your time. I tell you what AI can realistically do about it, and which package fits. If coaching isn’t the right fit, I’ll say so.

02

Two-hour working sessions Weekly or bi-weekly

You share your screen and your real files. We build the tool together, and I explain what we’re doing and why as we go. The learning happens as a byproduct of building, so by the end you can build the next one without me.

03

You leave with it running Every session

A working tool, the recording and transcript, and a follow-up email with lessons learned and homework. Bring your team to any session; I recommend keeping the group small so everyone stays focused. The tools we build are usually shareable, so one session’s work can give hours back to several people. Between sessions, email me with anything.

In their words

From people who run real companies.

Dylan has not only saved me hundreds of hours of work, he opened my mind to growth I never thought possible. Social media, email marketing, audio transcriptions, deep searches for new clients — most of it happens while I sleep. Trust me, Dylan is worth your investment.
John TeshBroadcaster & Entrepreneur

Built together

  • 01A paid Pain & Mobility program at tesh.com
  • 02Decades of radio archive turned into a content engine
  • 03Spec spots in his voice for the sales team, in minutes
  • 04Runs Codex and Claude himself now, no developer needed
3:05

“Tasks that took me two, three, four hours now take literally minutes. Projects I’d put off for five years, done in a couple of days.”

Brad BaileyOwner, Bailey Boys Services
1:36

“He built a scraper that pulls every coder job post in the country. It’s saved us over $100,000 in time, and we’ve closed three deals from it, north of $500,000 each.”

Joe StefanskiGrowth & Finance, Kode Health
2:55

“Five to fifteen new stories every day that we weren’t producing before. One person is more effective, so I didn’t have to hire that second person.”

TJ MontemerOwner, Mirror Media Group
Menu costing went from over a week to about ninety minutes.

“Our team now uses AI for cash reconciliation across seven properties, payroll review, dashboards, and marketing.”

Sean TaylorFounder & CEO, Taylor Hospitality Group
A live SaaS product, built with AI instead of a developer.

“Eight sessions later, I’m running a live product with payments, a self-filling CRM, and onboarding. If you want to ship real software with AI instead of engineers, just hire Dylan.”

Ken SavageFounder, AutoM8
Book a free 30-minute call

Coaching from $9,000 · full pricing below

Dylan Davis, AI executive coach Dylan Davis
Who you’re working with

What I do, in plain terms.

I build AI systems and automation for a living. I did it inside Mastercard, HSBC, and Bank of America, and I do it now with business owners and executives across law, hospitality, aviation, media, education, and more. I also make free videos about it on YouTube.

What I sell is leverage: the ability to do things your current headcount can’t, and to get hours back from the things it already does. The fastest way I’ve found to give a leader that is to build something real, on their own workflow, next to someone who does this every day and has seen where the models break. That’s what the sessions are.

Fortune 500Mastercard, HSBC, Bank of America
Dylan Davis AIFree videos on YouTube
One-on-oneLive two-hour working sessions
Pricing

Three packages. Same sessions, same support.

Start
4sessions
4 weeks weekly · 8 weeks bi-weekly

One or two working tools. Best when there’s one task you want gone from your week.

$9,000
Transform
12sessions
12 weeks weekly · 24 weeks bi-weekly

A system your team runs without you. Multiple departments, with you leading the rollout instead of a vendor.

$25,000

100% satisfaction guarantee

We keep working together until you have AI tools saving you 10+ hours a week.

Not sure which fits? That’s what the call is for.

Book a free 30-minute callNo obligation
Is this for you

Honest fit.

This is for you if

  • You’d rather use AI than read about it
  • A recurring task is eating your week
  • You’ll share your screen and drive
  • You can protect a two-hour block, weekly or bi-weekly
  • You want to lead your company’s use of AI, not outsource it

This isn’t for you if

  • You want it built for you rather than with you
  • You have no interest in how it works
  • You can’t protect the time for regular sessions
  • You want a one-time fix, not a skill
Questions

Before you book.

Which package should I start with?

Match it to how much you want to build. One use case is usually a four-session job. Two or three use cases, plus rolling them out to your team, is usually eight. If you finish with more you want to build, you add another package.

What do I actually get?

Working tools built on your own workflow. The recording and transcript of every session. A follow-up email after each one with lessons learned, resources, and homework. Email support between sessions. And the skill to build the next tool without me.

What if I’m not technical?

Good. Most of my clients had never written a line of code when we started. You share your screen, I guide, you drive. Brad, Joe, and Sarina above all said the same thing.

Have you done this in my industry?

Most likely, yes. Private equity, law, hospitality, aviation, media, education, healthcare, accounting, lending, home services, commodities, and more. Most problems have the same shape: take in a lot of information, then make a decision or produce an output. The industry changes the words, not the build.

How quickly will I see results?

Usually in the first session. Ben’s full-day market analysis ran in 45 minutes after one session, and Scott’s 18-month data problem was solved in one. You leave every session with something working, so the results start the same day and add up as you build more.

Next step

Bring the task that takes the most of your week.

A free 30-minute call. You tell me what takes your time, I tell you what’s realistic, and we pick a package. If coaching isn’t the right fit, I’ll say so.

Book a free 30-minute callCoaching from $9,000