A course gives you information. A coach gives you advice. I give you AI systems built and running inside your business. Engagements start with a paid AI Audit and graduate into a monthly retainer where I do the actual implementation — not just recommend it.
Most clients start with the AI Audit ($999, one-time) — a full workflow review with the top 3–5 AI opportunities and a written implementation roadmap. From there, most move directly into AI Management ($1,999/mo, month-to-month) where I build 1–2 systems in month 1 and add new automations as the business grows. Founders and SMBs who want full strategic ownership move up to the Fractional AI Officer retainer ($3,500/mo, month-to-month).
I co-founded Milo (an AI CRM for home service businesses) and have built and shipped multiple AI tools for real businesses — outreach automation, lead follow-up, CRM intelligence, content pipelines. I consult on what I've actually built and run, not theory.
Founders 0–18 months in with a real product, and SMBs with established revenue (typically $250K+ ARR) looking to use AI to compress operational cost or expand sales capacity. If you have repeated workflows, customer touchpoints, or sales motions — there's almost always something to automate.
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 90-minute discovery call, a workflow review across your sales / ops / admin functions, written report covering the top 3–5 AI opportunities prioritized by ROI and effort, a recommended build sequence, and a 60-minute delivery walkthrough where we go through the roadmap together. The roadmap is yours to keep — you can execute it yourself, hand it to your team, or hire me to run it.
Roughly 7 calendar days from kickoff to delivery. Your time investment is typically 2–3 hours total — discovery call, a workflow walkthrough, and the delivery call.
No. The audit is one-time and standalone. Most clients move into AI Management because the roadmap creates an obvious next step — but there's no obligation. The roadmap is yours either way.
Yes. The roadmap is delivered as a shareable document. Use it however helps — internal alignment, board updates, vendor briefs, or your own implementation.
1–2 of the highest-ROI systems from your audit roadmap, fully built, integrated with your existing tools, and deployed into your business. Setup is included — no hidden onboarding fee.
Ongoing monitoring and optimization of what's already built, plus new automations added each month as your business grows or new opportunities surface. You also get async support for questions and small changes, and a monthly performance report.
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.
You do. All deliverables — code, prompts, configurations, documentation — are yours. If you ever cancel, the systems keep running and you keep the keys.
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.
The audit is paid in full upfront. Retainers (AI Management, Fractional AI Officer) are billed at the start of each month. Payment by card, ACH, or invoice — whichever works for your accounting setup.
If I haven't started work on your audit, full refund — no questions. Once the discovery call has happened or work has begun, fees are non-refundable. Retainer fees are not refundable for partially-completed months, but you can cancel any time and you won't be billed for the next 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.
Audit kickoff is typically within 5 business days of payment. Retainers begin the month following the audit (or the following month if you skip the audit and apply directly).
Email carter@cartersimmons.org — I read and reply personally.