The technology is easy. Adoption is the hard part.
AI doesn’t deliver because tools get installed — it delivers when your people actually use them. We get your team fluent and bought-in, from a free peer roundtable to AI Sherpa, a guided 3-month program, to an alignment and planning workshop that isn’t only about AI. Practitioner-led, no theory, prices on the page.
Most AI fails at adoption — not the tech.
The model works. The pilot demos fine. Then it dies in the gap between “we bought it” and “our people use it every day.” That gap is change management — and it’s where we’ve spent two decades, running high-stakes workshops for operators long before AI.
These formats meet your team where they are: a low-stakes peer conversation, a guided program for your leadership team, a facilitated alignment and planning workshop, or a hands-on crash course. Pick the on-ramp that fits.
Four ways to build the muscle.
From free to hands-on. Each stands on its own — and each is a natural on-ramp into the work itself.
Table Stakes Roundtable
A peer roundtable — an honest conversation about AI with operators your size. No vendors, no pitch, no slides. What’s said in the room stays in the room.
Who it’s for: Owners, CEOs, COOs, and CFOs who want unfiltered peer input, not a demo.
See Table StakesAlignment & Planning Workshop
A facilitated working session on a decision in front of you: a system to replace, portals to unify, a process that outgrew its tools, or where AI pays off. We get the stakeholders in one room, map how the work really flows, agree on what matters and in what order, and leave you with written findings, the priorities, and a plan for what comes next.
Who it’s for: Leadership teams that need alignment and a plan before committing money to a project, a platform, or an AI initiative.
Talk about a workshopAI Sherpa
A guided program that takes a leadership team from “we should do something with AI” to fluent, aligned, and pointed at the right first automation — with a senior guide and your own business as the material.
Who it’s for: Leadership teams who want to learn before they build, or build with their eyes open.
How AI Sherpa worksAI & Automation Crash Course
Hands-on team training that turns curiosity into capability — your management team using AI on real work by the end.
Who it’s for: Leadership teams getting everyone to a shared, practical baseline.
Ask about a crash courseBring something to work on: the prompt library is the starting material for crash courses and workshops — copy-paste prompts by role, free.
AI Sherpa: get fluent, get aligned, then build.
Most leadership teams don’t have an AI problem — they have an alignment problem. Half the room is skeptical, half is over-excited, and nobody agrees on what to do first. AI Sherpa is three months with a senior guide who has shipped this work inside companies your size, working on your business, not case studies.
You come out the other side fluent in what these tools actually do, clear on where they pay off in your operation, and pointed at a first automation that’s worth doing — ready to go as the first month of AI Office, if you want to go on.
AI Sherpa is not a course, not a retainer, and not consulting by the hour. It is three months with a guide and a decision at the end — and it stops at three months on purpose. In businesses our size, that is where it reaches its full usefulness. Past that, you should be building.
AI Sherpa
- A senior AI strategist dedicated to your business for the cycle
- A weekly working session with your leadership team — your real workflows, data, and constraints as the material
- Executive AI coaching for you and your leaders
- A living AI roadmap: where AI pays off first, what to ignore, which vendors to trust
- Independent vendor and tool advisory, plus Slack and email access between sessions
- A scoped first automation at the end of the three months — yours to run with us or without us
AI Sherpa teaches your people. If you want a technology executive making the calls for you, that’s the Fractional CTO. See Fractional CTO/CAIO.
Training is the on-ramp. The work is the destination.
Enablement gets your team ready; then the work starts. AI Sherpa or a workshop flows naturally into an AI Office retainer — and the same team runs all of it.
Partner, not vendor.
It’s amazing how the programmers and staff are almost melted together with our staff — it’s hard to figure out where one stops and the other begins, because they truly are a team.
I’ve been working with software designers for over 25 years. Frogslayer understands our needs and meets deadlines. They’re a true partner.
Five steps, every time.
For training, “Engage” is the session or the cycle itself — and the first automation it points you at.
- 01Discovery Call30–60 min
You tell us the problem in your words. We tell you straight whether — and where — we can help. No slides.
- 02Deep Dive60–90 min
The people closest to the problem, in one room (or one call). We get to the real constraint and the number that matters.
- 03Proposal & Paperworkdays, not weeks
Scope, price, and timeline in writing. A standard MSA and a short SOW — no 50-page lock-up.
- 04Prep & Kickoffweek 1
Access, environments, and a kickoff with everyone who touches the work. You know who’s on it and what ships first.
- 05Engageongoing
The work itself — visible every week, in your environment, with your people in the loop.
Straight answers.
Do we have to be an AI Office client to do training?
No — every format stands alone. The Table Stakes roundtable is free; AI Sherpa, workshops, and crash courses are bought on their own. Many AI Sherpa clients go on to AI Office, but nothing requires it.
What’s the difference between AI Sherpa and AI Office?
AI Sherpa gets your leadership team fluent and aligned over three months and ends with a first automation scoped. AI Office is the team that builds — a monthly retainer for operators ready to ship. AI Sherpa first, then AI Office, is the most common path; skipping straight to AI Office is fine if you already know what you want built.
What’s the difference between AI Sherpa and a Fractional CTO?
AI Sherpa teaches your people; the Fractional CTO is your technology executive. One builds your team’s judgment; the other exercises judgment on your behalf.
Who should attend?
The people who will act on the result. For AI Sherpa and the Alignment & Planning Workshop, that is the leadership team plus the people who know the work in question. For the crash course, it is the managers and teams who will use AI day to day.
Is it hands-on or just slides?
Hands-on. By the end of a crash course your team is using AI on real work; a workshop ends with written findings and a plan your team helped make; AI Sherpa runs on your own workflows. No lecture-only formats.
Can you run it on-site?
Yes. We deliver in person where geography allows (the crash course has a virtual option), and we tailor the material to your business and tools.
How is it priced?
Roundtable: free. AI Sherpa: $7,500 per 3-month cycle. Alignment & Planning Workshop: from $4,500, scoped to the number of days and the size of the group. Crash courses are quoted by inquiry. Nothing is bundled or waived — every format is priced on its own.
Get your team fluent and moving.
Tell us your team and your timeline. We’ll recommend the right format — or just start with a seat at the next roundtable.