Is this a fit?
Provide ongoing AI support for 3-5 small businesses — setting up tools, building automations, training teams, and continuously optimizing their AI stack month over month.
Skills to bring or develop
- AI Tool Setup
- Automation Building
- Team Training
- Project Management
The starting sequence
- Define your retainer scope and monthly deliverables
- Land 1 pilot client at a discounted rate
- Build repeatable onboarding and delivery workflows
- Scale to 3-5 concurrent clients
- Systematize with SOPs so delivery takes less time each month
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
Founder / CEO at growing small business
Company size
10-50 employees
Industry
Professional Services / E-commerce
Problems to investigate
- Knows AI could help but nobody on team knows how to implement
- Tried a one-off AI consultant but changes did not stick
- Team reverts to old workflows within 2 weeks of any change
- Wasting money on AI tool subscriptions nobody uses
- Competitors are using AI and pulling ahead
Channels to test
- Referrals
- Cold Email
- Communities
First launch approach
Deliver massive value, then convert to full-price retainer.
Ways to find your first customer
- Reach out to 10 businesses you have already helped with AI informally
- Post on LinkedIn: "I am taking on 3 pilot clients for ongoing AI implementation"
- Partner with business consultants who hear "we need AI help" from their clients
- Offer a free AI workflow assessment as the entry point
- Join small business owner communities and answer AI questions
Content ideas
- The 5 automations I build for every new client
- Why one-off AI consulting does not work (and what does)
- Monthly AI implementation report — real results from a real client
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.
Essentials
$2,500/mo example price
- 10 hours of AI implementation per month
- 2 new automations built
- Monthly strategy call
- Email support (48hr response)
- Monthly progress report
Growth
$4,000/mo example price
- 20 hours of AI implementation per month
- 4 new automations built
- Bi-weekly strategy calls
- Team training sessions (2/mo)
- Slack support (24hr response)
- Tool stack management
Scale
$5,000/mo example price
- 30 hours of AI implementation per month
- Unlimited automations
- Weekly strategy calls
- Unlimited team training
- Priority Slack support (same-day)
- AI tool evaluation and procurement
- Quarterly AI roadmap
Build and deliver the offer
Service delivery
Packages
Name
AI Stack Setup
Deliverables
- 2-3 automations built (Zapier/Make)
- Tool selection + setup
- Team training session
Timeline
1-2 weeks
Included in this example
- Workflow mapping session
- Documentation for the client team
Name
Monthly AI Retainer
Deliverables
- Ongoing automation builds/fixes
- Monthly team training/office hours
- Tool stack optimization
Timeline
Ongoing, monthly
Included in this example
- Priority support for broken automations
- New automation requests (capped per month)
Client onboarding
Step
Map current manual workflows worth automating
Who handles it
you
Step
Get access to the tools that need connecting (CRM, email, etc.)
Who handles it
client
Step
Build and test first automation end-to-end
Who handles it
you
Step
Train the team on the new workflow
Who handles it
you
Kickoff conversation
- Map the 3-5 highest-value manual workflows to automate first
- Confirm tool access and any security/compliance constraints
- Set the training cadence for the team
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.
0 of 17 tasks checked
01 · Foundation 3 days · suggested pace
Build your retainer delivery system and service definition
Write out exactly what each tier includes per month: number of automations, hours, meetings, support level. Create a one-page scope document you can share with prospects. Be specific — vague scope causes scope creep.
Target deliverable: Retainer scope document with 3 tiers
Tool examples: Notion, Google Docs
Planning allowance: 4 hours · AI can assist; review the output
Create an intake questionnaire, tool access checklist, first-30-days plan template, and kickoff meeting agenda. Every new client should go through the same onboarding so nothing gets missed.
Target deliverable: Client onboarding system
Tool examples: Notion, Google Forms, Loom
Planning allowance: 4 hours · AI can assist; review the output
Pre-build 10 common automations you can deploy for any client: email triage, meeting notes summary, invoice processing, social media scheduling, customer support routing, report generation, lead scoring, content drafting, data entry, calendar management.
Target deliverable: 10 reusable automation templates
Tool examples: Zapier, Make, ChatGPT
Planning allowance: 6 hours · AI can assist; review the output
Build a monthly report template that shows: automations delivered, hours saved, tools configured, team training completed, and next month priorities. Clients need to see the value to keep paying.
Target deliverable: Monthly report template
Tool examples: Notion, Google Sheets
Planning allowance: 2 hours
02 · Launch 7 days · suggested pace
Land your first pilot client and deliver massive value
Contact businesses in your network who you know struggle with manual processes. Frame it as a trial they can cancel anytime.
Target deliverable: 10 prospects contacted, 3 calls scheduled
Tool examples: LinkedIn, Email, Calendly
Planning allowance: 4 hours
On the sales call, walk through their current workflows and show them 3-5 quick wins you could implement in the first week. Present your scope document and pilot pricing. Close the deal.
Target deliverable: First pilot client signed
Tool examples: Zoom, Stripe, Google Docs
Planning allowance: 3 hours
Execute your onboarding checklist: get tool access, run intake questionnaire, hold kickoff meeting. Then immediately implement 2-3 quick-win automations so they see value in week one.
Target deliverable: Client onboarded + 2-3 automations live
Tool examples: Zapier, Make, ChatGPT, Notion
Planning allowance: 8 hours · AI can assist; review the output
At the end of month one, deliver a detailed report showing what was built, hours saved, and next month plan. This report is what converts the pilot into a full-price retainer.
Target deliverable: Month-one report delivered
Tool examples: Notion, Google Sheets, Loom
Planning allowance: 2 hours · AI can assist; review the output
03 · Scale 2 months · suggested pace
Grow to 3-5 retainer clients with systematized delivery
Use the month-one report to justify full pricing. Show the ROI: "I saved your team 40 hours this month — that is worth $X.
Target deliverable: Pilot converted to full-price retainer
Tool examples: Zoom, Google Sheets, Stripe
Planning allowance: 2 hours
Use your first client results as social proof. Post the case study on LinkedIn, ask for referrals, and reach out to 20 more prospects. Offer the discounted pilot to each new client.
Target deliverable: 2-3 new retainer clients signed
Tool examples: LinkedIn, Email, Calendly
Planning allowance: 8 hours
Document step-by-step how you build each automation, run each training session, and produce each report. As your library grows, each new client takes less time to serve.
Target deliverable: SOP library for all common deliverables
Tool examples: Notion, Loom
Planning allowance: 6 hours · AI can assist; review the output
Build a Notion or Airtable dashboard tracking all clients: active automations, hours used, next deliverables, renewal dates. This keeps you organized as you scale past 3 clients.
Target deliverable: Client management dashboard
Tool examples: Notion, Airtable
Planning allowance: 4 hours
04 · Exit 60 days · suggested pace
Prepare your AI implementation retainer business for sale, acquisition, or hands-off operation
Create comprehensive standard operating procedures covering every repeatable process in your AI implementation retainer 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
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
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
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
Create a teaser document (blind profile) for your AI implementation retainer 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
- Zapier
- Make
- Notion
- Loom
Tools to evaluate
Item
Zapier or Make
Why consider it
Named directly as the automation-building tool for both packages
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.
Operations Manager
Map this client's current manual workflow and flag the highest-effort steps
Backend Dev
Build and test this automation workflow end-to-end
Use the first task above as your opening prompt. Include your audience, desired output, constraints, and how you will judge quality.
Your first small test
- Choose one customer. Find five people who have the problem described in this guide.
- Show one useful sample. Ask about their current process, priorities, and objections.
- Offer a clearly scoped pilot. Agree on deliverables, a price to test, and what success means.
- 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.