AI strategy for
owner-led businesses
You don't need an AI department. You need one trusted advisor who knows your business, cuts through the noise, and helps you keep pace and build a real edge.
Three engagement levels
- AI Orientation
- You stay informed.
Know what matters. - $1K /qtr
- Most popular
- AI in Motion
- Build a roadmap.
Start executing. - $2.5K /qtr
- AI as Advantage
- Build a durable edge.
- $5K /qtr
Every owner knows AI matters
Many Aren't managing it strategically
You don't need an AI department. You need one trusted advisor who knows your business, cuts through the noise, and helps you keep pace, and build a real edge.
Hundreds of AI tools, zero framework for deciding which ones matter for your company.
AI tool providers can help, but their viewpoint is narrow and their advice comes from that viewpoint.
AI dabbling happens everywhere. Strategic AI adoption requires someone driving a plan.
Fractional CAIO services target $50M+ companies. AI freelancers sell training. Owner-led SMBs are stuck in between.
Hundreds of AI tools, zero framework for deciding which ones matter for your company.
AI tool providers can help, but their viewpoint is narrow and their advice comes from that viewpoint.
AI dabbling happens everywhere. Strategic AI adoption requires someone driving a plan.
Creating effective landing page for a digital agency.
Most AI services are either too technical, too generic, or quietly selling you something
Owner-led businesses need something different
The Fractional AI Director service is offered through Phimation Strategy Group, a strategic advisory practice built specifically for owners and leaders of small private companies.
Dave Haviland's work sits at the intersection of business strategy, investor discipline, and practical execution. He brings the same framework-driven, probabilistic thinking to AI adoption that he brings to every engagement: identify the 4–6 variables that actually determine outcomes, build conviction, and act with clarity.
This service is a natural extension of 25 years advising companies exactly like yours.
- Annual AI Opportunity Scan: guided evaluation of your needs and opportunities
- Quarterly AI Strategy Brief: a look ahead, filtered for your business
- Quarterly Review Session: 60-min call with prioritized 90-day recommendations
- Email access for quick questions and gut-checks
- Everything in Tier 1
- Working Session: an additional 60-min call per quarter
- AI Pulse: quarterly proprietary briefing on how your organization is actually using AI and where the leverage is
- AI Roadmap: a 4-quarter build plan for your business
- Everything in Tiers 1 & 2
- Quarterly Review extended to 2 hours
- One additional working session per quarter
- AI Pulse run monthly, if wanted
- Tool Selection Support: buy/build/skip recommendations with rationale
- Market Analysis: customized quarterly read on what your market, customers, and competitors are doing
- Frameworks: custom framework development for your business
Credentials:
By the numbers:
Start where you are,
Scale as you go
Three engagement levels designed for different stages of AI maturity, and different levels of ambition.
- Everything in Tiers 1 & 2
- Quarterly Review extended to 2 hours
- One additional working session per quarter
- AI Pulse run monthly, if wanted
- Tool Selection Support: buy/build/skip recommendations with rationale
- Market Analysis: customized quarterly read on what your market, customers, and competitors are doing
- Frameworks: custom framework development for your business
Tier 1
AI Orientation
- Annual AI Opportunity Scan: guided evaluation of your needs and opportunities
- Quarterly AI Strategy Brief: a look ahead, filtered for your business
- Quarterly Review Session: 60-min call with prioritized 90-day recommendations
- Email access for quick questions and gut-checks
Tier 2
AI in Motion
- Everything in Tier 1
- Working Session: an additional 60-min call per quarter
- AI Pulse: quarterly proprietary briefing on how your organization is actually using AI and where the leverage is
- AI Roadmap: a 4-quarter build plan for your business
Tier 3
AI as Advantage
- Everything in Tiers 1 & 2
- Quarterly Review extended to 2 hours
- One additional working session per quarter
- AI Pulse run monthly, if wanted
- Tool Selection Support: buy/build/skip recommendations with rationale
- Market Analysis: customized quarterly read on what your market, customers, and competitors are doing
- Frameworks: custom framework development for your business
Simple And Powerful
A rhythm that pushes and paces your AI development.
We do a guided assessment of your business, how people are using AI, what tools you're using, where the highest-leverage opportunities are, and what the right 2–4 priorities to attack next.
You receive a curated brief, not a news roundup, and not a high-level vision, but a look ahead 2–3 years into the future from the perspective of your business. Shows up in your inbox, no prep required.
We assess progress on the prior quarter's priorities, decide what changes, and lock the next 90-day plan. A high-leverage hour each quarter.
You get a regular look inside your company, with a proprietary assessment of your team's AI usage patterns that tells you whether adoption is actually working, where the leverage is being left on the table, and where to focus next. It's the management system that turns individual AI experimentation into organizational capability.
Between reviews, working sessions are where we build, evaluating tools, assessing workflows, preparing team briefings, or problem-solving whatever's in motion. Used on your highest-leverage needs.
Hundreds of AI tools, zero framework for deciding which ones matter for your company.
AI tool providers can help, but their viewpoint is narrow and their advice comes from that viewpoint.
AI dabbling happens everywhere. Strategic AI adoption requires someone driving a plan.
Fractional CAIO services target $50M+ companies. AI freelancers sell training. Owner-led SMBs are stuck in between.
Know where you are,
and where to head
The Scan is the entry point for every engagement, a structured diagnostic that maps AI opportunity to your specific business, not a generic framework.
- Annual AI Opportunity Scan: guided evaluation of your needs and opportunities
- Quarterly AI Strategy Brief: a look ahead, filtered for your business
- Quarterly Review Session: 60-min call with prioritized 90-day recommendations
- Email access for quick questions and gut-checks
- Everything in Tier 1
- Working Session: an additional 60-min call per quarter
- AI Pulse: quarterly proprietary briefing on how your organization is actually using AI and where the leverage is
- AI Roadmap: a 4-quarter build plan for your business
- Everything in Tiers 1 & 2
- Quarterly Review extended to 2 hours
- One additional working session per quarter
- AI Pulse run monthly, if wanted
- Tool Selection Support: buy/build/skip recommendations with rationale
- Market Analysis: customized quarterly read on what your market, customers, and competitors are doing
- Frameworks: custom framework development for your business
- Current AI use:
what tools are in the building and how systematically they're being used - Functional AI potential:
realistic uplift per function: sales, ops, service delivery, marketing, finance - Readiness factors:
data availability, team openness, technical infrastructure - Risk factors:
where AI could create problems if applied carelessly - Sequencing:
which moves to make first, and why the order matters
what tools are in the building and how systematically they're being used
realistic uplift per function: sales, ops, service delivery, marketing, finance
data availability, team openness, technical infrastructure
where AI could create problems if applied carelessly
which moves to make first, and why the order matters
Know whether AI
is actually working
Most companies have no idea whether their AI adoption is producing real value or just creating the appearance of productivity. The AI Pulse is how you find out.
- Annual AI Opportunity Scan: guided evaluation of your needs and opportunities
- Quarterly AI Strategy Brief: a look ahead, filtered for your business
- Quarterly Review Session: 60-min call with prioritized 90-day recommendations
- Email access for quick questions and gut-checks
- Everything in Tier 1
- Working Session: an additional 60-min call per quarter
- AI Pulse: quarterly proprietary briefing on how your organization is actually using AI and where the leverage is
- AI Roadmap: a 4-quarter build plan for your business
- Everything in Tiers 1 & 2
- Quarterly Review extended to 2 hours
- One additional working session per quarter
- AI Pulse run monthly, if wanted
- Tool Selection Support: buy/build/skip recommendations with rationale
- Market Analysis: customized quarterly read on what your market, customers, and competitors are doing
- Frameworks: custom framework development for your business
Each month, the system scans the organization's actual AI use and applies a structured assessment that surfaces patterns leadership can't see: where AI is creating real value, where adoption is lagging, what one person has figured out that nobody else knows yet, and what individuals and the organization should focus on next.
- Usage patterns:
how your team is engaging with AI across functions, and whether those patterns are building organizational capability or just individual efficiency - Leverage gaps:
where AI could be creating more value than it currently is, and why - Emerging practices:
what's working inside the organization that's worth spreading - Development priorities:
the highest-leverage areas to work on
- A leadership team that actually knows what's happening with AI in their organization, and has a plan for making it better every month.
Built for owner-led businesses
This service was designed for a specific kind of company, and it works because it was designed specifically, not generically.
Substantial enough to have something to protect and grow. Small enough that every decision matters and executive time is scarce.
Owner-operated businesses where the owner is also the strategist, and where trust and long-term thinking matter more than quarterly reporting.
Professional services, consulting, managed services, trade services. Businesses where the product is expertise and relationships, not widgets.
Big enough to have functional specialization. Small enough that AI adoption needs to be sequenced carefully against team bandwidth and company resources.
Find out where AI can move the needle
Start with the AI Opportunity Scan, a structured diagnostic that tells you exactly where to focus and in what order. Or book a call to talk through where you are.