A course gives you information. A coach gives you advice. I build and run AI systems inside your business. Engagements start with a free qualifying call and audit, then move into a monthly retainer where I do the actual implementation — not just recommend it.
Every engagement starts with a free qualifying call — no commitment, no pitch. We identify where AI will actually move the needle in your business. From there, most clients start on the AI Pilot — one system built and live by Day 7, audit included — to prove the concept with minimal risk. Once the value is clear (usually by month 3), clients graduate to AI Management, where AI becomes a permanent function: one new system ships every month, everything running gets maintained, and you get a monthly report. Founders and SMBs who want full AI strategy ownership move up to the Fractional AI Officer retainer, by application.
I've built and shipped two AI products from scratch, solo — Milo (an AI CRM for home service contractors) and HireRecruitAI (an AI recruiting platform). I build and run AI systems inside client businesses every day. You're hiring someone who does the work, on what I've actually shipped and run, not theory.
SMBs with established revenue — typically $250K+ ARR — looking to use AI to compress operational cost, scale without adding headcount, or expand sales capacity. If your business has repeated workflows, customer touchpoints, or a sales motion, there's almost always something worth automating.
Tampa-first — I'm based in Tampa, FL and prefer to do kickoffs in person when possible. Working nationwide remotely otherwise. Time-zone overlap with US business hours is required for retainer clients.
A 30–45 minute call where I review your workflows, identify the top 3–5 AI opportunities ranked by ROI, and map what to build. You'll leave with a clear picture of where AI will move the needle in your business — no cost, no obligation.
Yes. The qualifying call and audit are included at no cost. If we're a fit and you want to move forward, that's when the retainer starts. No pressure either way — the call is genuinely about figuring out if there's a real opportunity in your business.
The qualifying call is 30–45 minutes. If you move into the AI Pilot retainer, Month 1 is where the full audit, pilot build, and delivery walkthrough happen — typically 7 calendar days from kickoff to live system.
Yes. The roadmap delivered in Month 1 is yours to share — internal alignment, board updates, vendor briefs, or your own implementation.
The Pilot is about proving the concept — one system, live fast, low risk. AI Management is about making AI a permanent function in your business. Instead of maintaining one system, I'm shipping a new one every month, running everything in the background, and owning the roadmap with you. Different scope, different intent.
One full-scale AI system per month — outreach engines, CRM intelligence layers, support agents, content pipelines, proposal systems, and similar. Each is scoped to your business and shipped that month. All existing systems stay monitored and maintained in parallel.
No — if you already know AI works for your business and you want to move fast, you can start on Management directly. Most clients come through the Pilot first because it's lower risk, but it's not a requirement.
No. AI Management is month-to-month. Cancel anytime. No long-term contract.
Outreach and prospecting automation, AI-powered follow-up, intake bots, CRM intelligence layers, content engines, internal-ops automations, customer-support agents, and similar. The audit determines exactly what — every business is different.
Your systems are built, hosted, and maintained as part of your retainer — you get full use of everything they do for your business while we work together. They run on managed infrastructure and keep improving every month. It’s month-to-month with no lock-in: if you ever pause, the managed service ends.
While you're on a retainer, you get full use of everything I build for your business — wired into your own tools and accounts wherever possible. I build, host, and maintain the systems and the engine behind them as part of the service, so they keep working as models and APIs change. Month-to-month, no lock-in. Want to own and self-host a specific build outright? We can scope that separately.
SMBs that want full AI strategy ownership rather than just execution — companies large enough to benefit from a senior AI voice in the room, but not large enough (or not ready) to hire a full-time AI lead. I act as a fractional executive, owning the roadmap, building the big systems, training the team, and reporting ROI.
Strategic depth and priority. Fractional AIO includes 2 strategy calls per month (vs. async-only on Management), 1 major system built per quarter (vs. 1–2 in month 1 then incremental), team training and tool stack management, monthly ROI reporting, priority Mon–Fri response, and first-in-line same-week turnaround on new builds.
Yes — and it's the most common path. Most Fractional AIO clients started on Management and graduated when their AI footprint outgrew the lighter retainer.
All retainers are billed at the start of each month. Payment by card, ACH, or invoice — whichever works for your accounting setup. The qualifying call is free.
Once a billing cycle has begun, retainer fees are non-refundable for that month. You can cancel any time with 30 days written notice and you won't be billed for the following month.
Every engagement is covered by a mutual NDA by default. Your business data, customer information, and proprietary processes stay private. I don't share client information, never use your data to train external models, and follow least-privilege access on every integration.
I integrate with what you already have whenever possible — HubSpot, Salesforce, Pipedrive, Notion, Google Workspace, Slack, Stripe, etc. If a tool genuinely needs replacing, that's part of the audit recommendation — but I won't push a switch unless it's the right call.
Underlying API and tool costs (OpenAI, Anthropic, third-party SaaS, etc.) are passed through to you and billed directly to your accounts. I'll forecast these in the audit so there are no surprises, and they're typically a small fraction of what the systems save or earn.
The qualifying call is typically scheduled within 2–3 business days of booking. If we're a fit, your retainer can start the following month — Month 1 is when the audit and pilot build happen.
Email carter@cartersimmons.org — I read and reply personally.