Is this a fit?
Serve as the part-time AI strategy leader for 3-5 companies. Set AI roadmaps, evaluate tools, manage implementations, and train leadership — without anyone hiring a full-time CAIO.
Skills to bring or develop
- AI Strategy
- Executive Communication
- Change Management
- Tool Evaluation
- Business Analysis
The starting sequence
- Build your AI strategy framework and assessment toolkit
- Position yourself as a fractional CAIO on LinkedIn
- Land first client through your professional network
- Deliver quarterly AI roadmaps and monthly implementation support
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
CEO / COO at mid-market company
Company size
50-500 employees
Industry
Professional Services / Manufacturing / Healthcare
Problems to investigate
- Board is asking about AI strategy and there is no plan
- Employees are using AI tools randomly with no governance
- Competitors are moving faster on AI adoption
- Previous AI initiatives failed due to lack of leadership
Channels to test
- Referrals
- Partnerships
- Content Marketing
First launch approach
Position as a thought leader on LinkedIn with daily posts about AI strategy. Leverage existing executive network. Offer a free AI maturity assessment as the entry point.
Ways to find your first customer
- Publish a LinkedIn article: "Why your company needs a CAIO (but not a full-time one)"
- Reach out to 20 CEOs/COOs in your network with a personalized AI assessment offer
- Partner with management consultants and PE firms who advise portfolio companies
- Speak at industry events or host webinars on AI strategy for executives
- Ask satisfied clients from previous work for warm introductions
Content ideas
- How I build an AI roadmap for a new client in 2 weeks
- AI tool evaluation: what I recommend to my clients right now
- Fractional CAIO vs full-time hire — when each makes sense
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 Advisor
$5,000/mo example price
- 8 hours per month
- Monthly AI strategy session
- Tool recommendations and evaluations
- Email support
- Quarterly AI roadmap
Fractional CAIO
$10,000/mo example price
- 20 hours per month
- Weekly leadership meetings
- AI implementation oversight
- Team training sessions (2/mo)
- Vendor evaluations and negotiations
- Slack access for real-time questions
- Board presentation support
Full Engagement
$20,000/mo example price
- 40 hours per month (half-time)
- Daily standups with leadership
- Full AI transformation program management
- All team training and change management
- Budget management and vendor contracts
- Recruiting and hiring AI talent
- Board and investor presentations
Build and deliver the offer
Service delivery
Packages
Name
Fractional AI Officer Retainer
Deliverables
- AI roadmap document
- Monthly leadership briefing
- Tool evaluation + vendor management
Timeline
Ongoing, monthly (typically 5-10 hrs/week per client)
Included in this example
- Quarterly strategy review
- Change-management support for team AI adoption
Outside this example
- Hands-on implementation work (routed to an implementation partner or in-house team)
Client onboarding
Step
Interview leadership on business goals and current AI usage
Who handles it
you
Step
Audit current tools/workflows for AI opportunity
Who handles it
you
Step
Present roadmap and get leadership sign-off on priorities
Who handles it
you
Kickoff conversation
- Align on the 90-day roadmap priorities with leadership
- Confirm reporting cadence and who else needs visibility
- Set the boundary between strategy advice and hands-on implementation
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 5 days · suggested pace
Build your AI strategy toolkit and executive positioning
Create a structured assessment covering 6 dimensions: data readiness, tool adoption, process automation, team capabilities, governance, and strategic alignment. Score each dimension 1-5. This becomes your diagnostic tool for every new client.
Target deliverable: AI maturity assessment framework and scorecard
Tool examples: Notion, Google Sheets, ChatGPT
Planning allowance: 6 hours · AI can assist; review the output
Build a 90-day AI roadmap template in Google Slides: current state assessment, quick wins (30 days), strategic initiatives (60 days), transformation projects (90 days). Include budget estimates, resource requirements, and success metrics.
Target deliverable: AI roadmap template deck (20-30 slides)
Tool examples: Google Slides, ChatGPT, Notion
Planning allowance: 5 hours · AI can assist; review the output
Create your one-pager, case study template, and scope-of-work template. These need to look executive-grade — clean, professional, focused on outcomes and ROI. No flashy startup vibes.
Target deliverable: Professional one-pager + SOW template
Tool examples: Canva, Google Docs
Planning allowance: 4 hours
Rewrite your LinkedIn headline, about section, and featured section to position as a fractional AI officer. Post your first thought leadership article. Connect with 50 CEOs/COOs in target industries.
Target deliverable: LinkedIn profile optimized + first article published
Tool examples: LinkedIn, ChatGPT
Planning allowance: 3 hours · AI can assist; review the output
02 · Launch 14 days · suggested pace
Land your first client through network and content
Reach out to CEOs and COOs in your network. Offer a complimentary AI maturity assessment (90-minute call + written report). This is your top-of-funnel — executives who see the gaps hire you to fill them.
Target deliverable: 10 assessment calls completed
Tool examples: LinkedIn, Email, Calendly
Planning allowance: 8 hours
For each assessment, produce a professional report with scores, gaps, and recommended next steps. Schedule a follow-up call to present findings and propose your Fractional CAIO engagement.
Target deliverable: 10 reports delivered, 3-4 proposals sent
Tool examples: Google Slides, Notion, Zoom
Planning allowance: 12 hours · AI can assist; review the output
Follow up with the warmest prospects. Sign a 3-month minimum engagement. Get access to their tools and teams immediately.
Target deliverable: First retainer client signed
Tool examples: Zoom, Google Docs, Stripe
Planning allowance: 4 hours
Within the first 2 weeks, deliver a comprehensive AI roadmap. Present to the leadership team. This roadmap is what makes you indispensable — it shows the long-term vision they cannot execute without you.
Target deliverable: 90-day AI roadmap presented to leadership
Tool examples: Google Slides, Notion, ChatGPT
Planning allowance: 10 hours · AI can assist; review the output
03 · Scale 3 months · suggested pace
Build to 3-5 concurrent clients and establish thought leadership
Execute the first 30 days of the roadmap: deploy 3-5 AI tools, run training sessions, set up governance policies. Document measurable results (hours saved, costs reduced) for your case study.
Target deliverable: Quick wins implemented with measurable results
Tool examples: ChatGPT, Zapier, Notion, Loom
Planning allowance: 20 hours · AI can assist; review the output
Use your first client results as social proof. Publish a case study on LinkedIn. Ask for referrals. Continue offering free assessments. Target companies in the same industry as your first win.
Target deliverable: 2-3 additional retainer clients signed
Tool examples: LinkedIn, Email, Zoom
Planning allowance: 10 hours
Commit to 2 LinkedIn posts per week and 1 article per month on AI strategy topics. Share frameworks, anonymized client wins, and tool evaluations. Goal: become the person executives think of when they need AI guidance.
Target deliverable: Content calendar + 8 posts published
Tool examples: LinkedIn, ChatGPT, Notion
Planning allowance: 6 hours · AI can assist; review the output
Build a reusable 4-session AI training program for leadership teams covering: AI fundamentals, use cases by department, tool selection, and governance/ethics. Sell this as an add-on to the retainer.
Target deliverable: AI training curriculum (4 sessions)
Tool examples: Google Slides, Notion, ChatGPT
Planning allowance: 8 hours · AI can assist; review the output
04 · Exit 60 days · suggested pace
Prepare your fractional AI officer practice for sale, acquisition, or hands-off operation
Create comprehensive standard operating procedures covering every repeatable process in your fractional AI officer practice — 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 fractional AI officer practice 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
- Notion
- Google Slides
- Slack
Tools to evaluate
Item
Presentation tool (Google Slides, Notion, or similar) for the roadmap document
Why consider it
The AI roadmap document and monthly leadership briefing are named core deliverables
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.
Business Advisor
Draft an AI roadmap outline from these leadership interview notes
Product Manager
Draft the scope boundary section distinguishing strategy work from implementation work
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.