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Consulting · Full playbook

AI Executive & Team Trainer

Run paid AI workshops for businesses — for sales teams, marketing teams, executives, or entire companies. One client can be worth more than dozens of small consumer transactions.

Experience
Intermediate
Planning time
15-25 hours/week
Starter budget estimate
$100-$300

Illustrative planning ranges, not earnings projections. Check the full costs and customer demand for your own situation.

Is this a fit?

Run paid AI workshops for businesses — for sales teams, marketing teams, executives, or entire companies. One client can be worth more than dozens of small consumer transactions.

Skills to bring or develop

  • AI Tool Expertise
  • Training & Facilitation
  • Process Design
  • Change Management

The starting sequence

  1. Build your AI expertise portfolio
  2. Create workshop curriculum
  3. Offer free AI audits
  4. Land first corporate clients
  5. Scale with online courses and group training

What the work involves

You don't need to be an AI researcher or engineer. You need to be genuinely ahead of most business owners — comfortable inside tools like ChatGPT, Claude, Notion AI, or Make.com — and able to translate that fluency into plain language a 52-year-old operations manager can act on Monday morning. The real skill here is facilitation and change management, not coding. You're helping teams unlearn old habits and build new ones, which means you'll hit resistance, skepticism, and the occasional 'we tried that and it didn't work.' If you can stay patient, curious, and concrete in those moments, you have what it takes. If you need everyone to be excited before you can move forward, this will wear you out fast.

Find your first customers

Treat this customer profile as a starting hypothesis. Talk to people in this role and find out what they already do, what it costs them, and whether they want help.

Role

VP of Operations / COO

Company size

50-500 employees

Industry

Professional Services / Mid-Market

Problems to investigate

  • Team is curious about AI but nobody knows where to start
  • Wasting money on AI tools nobody actually uses
  • Competitors adopting AI faster
  • No internal AI expertise
  • Fear of AI replacing jobs creating resistance

Channels to test

  • LinkedIn
  • Local Networking
  • Referrals
  • Content Marketing

First launch approach

Offer free 30-minute AI readiness assessments to 20 businesses, convert top prospects to paid workshops

Ways to find your first customer

  • Post daily AI tips and tool reviews on LinkedIn
  • Offer free lunch-and-learn AI sessions to local businesses
  • Partner with HR consultants and business coaches
  • Speak at local chamber of commerce and industry events
  • Create a "Top 10 AI Tools for [Industry]" guide as lead magnet

Content ideas

  • How AI saved this team 20 hours/week
  • 5 AI tools every operations team should use
  • The real cost of NOT using AI in 2026
  • AI implementation mistakes that waste money

Shape the offer & delivery

These are example packages to adapt, not current market rates or promises of sales. Choose one deliverable, set a revision limit, and test the scope with a real buyer before expanding.

AI Audit

$1,500 example price

  • Tool assessment for your team
  • AI readiness scorecard
  • Top 5 quick wins report
  • 1-hour debrief call

Team Workshop

$3,500 example price

  • Half-day hands-on training
  • Custom to your industry
  • Prompt library for your workflows
  • Recording + materials
  • 30-day follow-up support

AI Transformation

$8,000/mo example price

  • Full implementation partner
  • Weekly training sessions
  • Custom SOPs for every department
  • Tool selection + setup
  • Ongoing optimization + support

Build and deliver the offer

Service delivery

Packages

Name

Team Workshop

Deliverables

  • Half-day or full-day AI training session for a team
  • Custom exercises using their real workflows

Timeline

1 day, scheduled 2-3 weeks out

Included in this example

  • Pre-session survey of team's current AI usage/gaps
  • Slide deck + exercise materials
  • Follow-up resource guide

Outside this example

  • Ongoing 1:1 coaching
  • Custom tool implementation

Name

Coaching Cohort

Deliverables

  • 6-week group coaching program, weekly live sessions

Timeline

6 weeks

Included in this example

  • Weekly live session
  • Private community/Slack for the cohort
  • Homework assignments applying AI to real work tasks

Name

Enterprise Retainer

Deliverables

  • Ongoing AI adoption advisory for an organization

Timeline

Monthly, quarterly-planned

Included in this example

  • Recurring training sessions
  • Tool evaluation and recommendations
  • Change-management support

Client onboarding

Step

Send a pre-training survey asking about the team's current AI tools, comfort level, and specific pain points

Who handles it

client

Step

Review a sample of the team's real work tasks so exercises use their actual context, not generic examples

Who handles it

client

Step

Confirm the org's AI usage policy/restrictions before designing exercises (some industries restrict specific tools)

Who handles it

you

Kickoff conversation

  • Understand the real barrier: is it skill, fear, unclear use cases, or organizational policy?
  • Identify 2-3 concrete workflows to use as live exercise material
  • Set the success metric for the engagement — usually a specific behavior change, not just "awareness"

Your launch roadmap

Work through the phases at your own pace. Durations and task hours are estimates; client conversations, sales, and other outcomes depend on the response you receive. Growth and exit steps are optional later decisions.

01 · Foundation 1 week · suggested pace

Build expertise portfolio and workshop materials

  1. Build a repeatable process for assessing a company's AI readiness — tools used, processes, pain points, quick wins

    Target deliverable: AI Audit Checklist + Scorecard

    Tool examples: Notion, Google Docs

    Planning allowance: 6 hours

  2. Create a half-day hands-on workshop with exercises, prompt libraries, and take-home materials

    Target deliverable: Workshop deck + materials

    Tool examples: Google Slides, Notion, Canva

    Planning allowance: 10 hours · AI can assist; review the output

  3. Create a 20-minute sample training video showing your teaching style and AI expertise

    Target deliverable: Demo reel for prospects

    Tool examples: Loom, ChatGPT

    Planning allowance: 4 hours · AI can assist; review the output

02 · Launch 2 weeks · suggested pace

Land first 2-3 corporate training clients

  1. Reach out to 20 businesses offering free 30-minute AI readiness assessment

    Target deliverable: 10 audits completed

    Tool examples: LinkedIn, Email, Loom

    Planning allowance: 10 hours

  2. Run a free "AI for Your Business" webinar to build authority and capture leads

    Target deliverable: 50+ webinar attendees

    Tool examples: Zoom, LinkedIn, Canva

    Planning allowance: 8 hours

  3. Follow up with audit prospects, pitch paid workshops

    Target deliverable: 2-3 paid workshops booked

    Tool examples: Email, Zoom, Google Docs

    Planning allowance: 6 hours

03 · Scale 2 months · suggested pace

Build recurring revenue and online presence

  1. Package workshop content into a self-paced online course for passive revenue

    Target deliverable: Online course live

    Tool examples: Teachable, Loom, Canva

    Planning allowance: 20 hours · AI can assist; review the output

  2. Post AI insights 5x/week on LinkedIn, grow to 5K+ followers

    Target deliverable: Authority in AI training niche

    Tool examples: LinkedIn, ChatGPT

    Planning allowance: 10 hours · AI can assist; review the output

  3. Pitch ongoing AI transformation packages to workshop graduates

    Target deliverable: 2 transformation retainers

    Tool examples: Email, Zoom, Notion

    Planning allowance: 8 hours

04 · Exit 60 days · suggested pace

Prepare your AI coaching and training business for sale, acquisition, or hands-off operation

  1. Create comprehensive standard operating procedures covering every repeatable process in your AI coaching and training business — client onboarding, delivery workflows, billing, and support. A buyer needs to run this without you.

    Target deliverable: Complete SOP handbook with video walkthroughs

    Tool examples: Notion, Loom, Google Docs

    Planning allowance: 12 hours · AI can assist; review the output

  2. Record the questions this step raises for your business, location, and circumstances. Confirm requirements and assumptions with current official sources and a qualified professional before acting.

    Target deliverable: Valuation estimate with supporting financials

    Tool examples: Google Sheets, ChatGPT

    Planning allowance: 6 hours · AI can assist; review the output

  3. Organize all financial records, contracts, customer data, IP documentation, and legal documents into a virtual data room that a buyer or their advisor can review.

    Target deliverable: Organized virtual data room

    Tool examples: Google Drive, Google Sheets

    Planning allowance: 10 hours

  4. Identify every area where the business depends on you personally. Delegate, automate, or document each one. Test by taking 2 weeks off and measuring impact.

    Target deliverable: Owner dependency scorecard (before/after)

    Tool examples: Notion, Zapier, Slack

    Planning allowance: 20 hours

  5. Create a teaser document (blind profile) for your AI coaching and training business and either list on marketplaces (Acquire.com, Flippa, Quiet Light) or reach out directly to 5-10 potential acquirers.

    Target deliverable: Teaser document + 5-10 buyer conversations started

    Tool examples: Acquire.com, Google Docs, Email

    Planning allowance: 8 hours · AI can assist; review the output

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Tools, budget & effort

These are tools named in the original playbook, offered as examples to evaluate. Check current capabilities, pricing, licensing, and data handling with the provider before subscribing. Start with the tools you already have.

  • ChatGPT
  • Claude
  • Midjourney
  • Notion
  • Loom

Tools to evaluate

Item

A presentation/workshop deck tool (Google Slides or Canva)

Why consider it

Paid workshops need real, polished delivery materials

Item

Zoom or similar for virtual workshop delivery

Why consider it

Many workshop clients want a remote-friendly option

Workshop delivery and virtual training
  • Zoom Webinars
  • Butter
  • Loom
Client deliverable and SOP documentation
  • Notion
  • Google Docs/Slides
  • Tango
CRM and client pipeline management
  • HubSpot CRM
  • Notion CRM template
  • Calendly

Make the numbers your own

Include setup, subscriptions, selling, fulfillment, revisions, support, and your time. Use your actual inputs and compare a cautious case with a better case.

Open the experiment calculator →

AI roles & prompt templates

Assign a clear job, provide approved inputs, and review the result. These are role and prompt ideas; this page does not run AI or connect your accounts.

Content Writer

Help me draft 3 hands-on exercises for a sales-team AI workshop

Sales Optimizer

Help me write an outreach message pitching a half-day AI workshop to a mid-size company

Copy a prompt, then add your context

Replace the bracketed placeholders. Use information you have permission to share, ask for sources, and check every factual or numerical claim.

Build a custom AI readiness audit for a prospective client
I run an AI coaching and training business. I have a discovery call coming up with a [INDUSTRY] company that has [NUMBER] employees and currently uses [LIST THEIR TOOLS]. They want to understand how AI could help their team.

Create a 15-question AI readiness audit I can send them before the call. The audit should cover:
1. Current workflow pain points (5 questions)
2. Existing tech stack and data hygiene (4 questions)
3. Team AI literacy and comfort level (3 questions)
4. Leadership buy-in and budget signals (3 questions)

For each question, include: the question itself, why I'm asking it (my internal note), and what a 'low readiness' vs 'high readiness' answer looks like. Format it as a Google Form-ready list I can copy directly.

Review requirements: Separate supplied facts from assumptions. Do not invent market data, customer results, testimonials, or source citations. Flag missing information and suggest a small validation test. Mark numerical examples as scenarios. Keep the final decision with me.
Write a workshop agenda and facilitator guide for a half-day AI training session
I'm delivering a half-day (4-hour) AI training workshop to a team of [NUMBER] people at a [INDUSTRY] company. Their primary roles are [JOB TITLES]. Their current AI experience level is [beginner/intermediate]. The business outcomes they want are [LIST 2-3 GOALS].

Create a complete facilitator guide including:
- A timed agenda broken into 30-minute blocks
- Learning objectives for each block
- 2-3 hands-on activities or exercises per block (specific, not generic)
- Suggested prompts or demos I can run live
- Common participant questions and how to answer them
- A 10-minute 'next steps' closing that leaves them with a concrete action plan

Make the activities specific to their industry and job roles. Avoid generic 'explore ChatGPT' exercises — give me real workflow-connected tasks they'll actually use Monday morning.

Review requirements: Separate supplied facts from assumptions. Do not invent market data, customer results, testimonials, or source citations. Flag missing information and suggest a small validation test. Mark numerical examples as scenarios. Keep the final decision with me.
Create a 90-day AI implementation SOP for a client's team
I need to write a 90-day AI implementation plan for a client. Here are their details:
- Industry: [INDUSTRY]
- Team size: [NUMBER]
- Current tools they use: [LIST]
- Top 3 workflow bottlenecks they want to solve with AI: [LIST]
- Budget for new AI tools: [MONTHLY BUDGET]
- Technical comfort of team: [LOW/MEDIUM/HIGH]

Create a 90-day phased implementation SOP with:
- Phase 1 (Days 1-30): Foundation — tool selection, team onboarding, first wins
- Phase 2 (Days 31-60): Integration — embedding AI into existing workflows, building internal prompts library
- Phase 3 (Days 61-90): Optimization — measuring time saved, expanding use cases, reducing friction

For each phase include: weekly milestones, who owns each task (role-based), success metrics, and a 'what to do if stuck' troubleshooting note. Format as a table I can drop into Notion or Google Docs.

Review requirements: Separate supplied facts from assumptions. Do not invent market data, customer results, testimonials, or source citations. Flag missing information and suggest a small validation test. Mark numerical examples as scenarios. Keep the final decision with me.
Generate a proposal and pricing package for an AI training engagement
I'm an AI coaching and training consultant. I just completed a discovery call with a potential client. Here's what I learned:
- Company: [INDUSTRY], [NUMBER] employees, [REVENUE RANGE if known]
- Their problem: [DESCRIBE PAIN POINT IN 2-3 SENTENCES]
- What they asked for: [WHAT THEY SAID THEY WANT]
- What I think they actually need: [YOUR ASSESSMENT]
- Their timeline: [WHEN THEY WANT TO START]
- Budget signals: [WHAT THEY SAID OR HINTED]

Write a professional proposal (not a template — a real one) that includes:
1. A one-paragraph 'situation summary' that proves I listened
2. Three tiered packages (Starter, Growth, Transformation) with clear deliverables, timelines, and prices in the range of $2,500 / $5,500 / $10,000
3. What's included and explicitly excluded in each tier
4. A ROI framing paragraph (time saved, errors reduced, capacity gained)
5. A clear call to action with a 7-day decision window

Tone: confident, specific, no fluff. Write it as if I'm sending it today.

Review requirements: Separate supplied facts from assumptions. Do not invent market data, customer results, testimonials, or source citations. Flag missing information and suggest a small validation test. Mark numerical examples as scenarios. Keep the final decision with me.

Build a personal AI team plan →

What a working week could look like

This is an example cadence. Include time for customer conversations, review, and admin; reduce the scope to fit your available hours.

What

Chief of Staff check-in — share one client win, one stuck point, one tool you tested

When

Daily · 15 min

What

LinkedIn content or direct outreach to niche contacts

When

Mon & Wed · 45 min

What

Tool and prompt testing — stay current, document what's useful for clients

When

Fri · 1h

What

Client delivery review — audit SOPs or workshop materials for accuracy and freshness

When

Sun · 1h

Problems to plan for

Use these playbook prompts to question your plan. Pricing, channels, and delivery models should be tested with your own customers.

Training people on AI tools instead of solving their actual business problems

Start every engagement with a workflow audit. Identify 2-3 specific tasks that eat time or cause errors. Design your training around those exact tasks. Measure time saved, not features learned.

Underpricing because you feel like you're 'just teaching'

Price by project or outcome, not by the hour. Anchor your pricing to the value delivered, not your time spent.

Taking on clients without change management buy-in from leadership

Before signing any engagement, require a 30-minute call with the decision-maker (not just the team lead). Confirm they'll attend the kickoff, send an internal communication endorsing the training, and set aside 30 minutes/week for follow-up during implementation. Make this a contract requirement.

Building a curriculum once and never updating it as AI tools change

Schedule a monthly 2-hour 'curriculum audit' block in your calendar. Update one module, test your demos, and note any tool changes. Treat your training materials like a living product, not a finished document.

Trying to serve every industry instead of picking a niche

After your first 3-5 clients, look at where you got results. Pick one or two industries and go deep. Build industry-specific case studies, prompts libraries, and SOPs. Your marketing becomes easier and your close rate goes up.

Your first small test

  1. Choose one customer. Find five people who have the problem described in this guide.
  2. Show one useful sample. Ask about their current process, priorities, and objections.
  3. Offer a clearly scoped pilot. Agree on deliverables, a price to test, and what success means.
  4. Record the evidence. Track responses, costs, hours, and what the buyer actually used. Decide whether to continue, change, or pause.

Explore related ideas

Adapted from Ashley’s Waymaker side-hustle playbooks, imported October 15, 2026. This is a published snapshot, not a live connection to your Waymaker account. Source examples are planning material, not verified customer outcomes. Explore Waymaker.

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