I help CEOs restructure their companies around AI. I know what it takes because I've already done it.
You know AI should be changing how your company operates. You've tried some tools, maybe hired someone, but you don't have a plan and you don't have the depth to lead this yourself yet.
You've tried ChatGPT. Maybe you bought a Copilot license or had someone build an internal tool. But nothing has fundamentally changed how your company operates. You're dabbling, not transforming.
The gap isn't awareness — you know AI matters. The gap is depth. You don't have a concrete plan that connects AI to your business model, your team structure, and your day-to-day operations. Meanwhile, your competitors are restructuring.
You need more than tools. You need a roadmap, a leaner team structure, and the personal fluency to lead the change — not just approve it.
A transformation partner, not another consultant with a slide deck.
You don't need more AI advice. You need someone who's actively restructuring their own company and can help you do the same — with a concrete plan, not theory.
What this is
- A 90-day AI implementation roadmap built specifically for your business, your team, and your margins
- A clear picture of what your team looks like in 6 months — who stays, what changes, where AI takes over
- Personal AI fluency deep enough to evaluate what your team is doing and lead the transition with credibility
- A thought partner who’s making these same restructuring decisions in his own company, in real time
- Direct access to someone who runs a real business — not a consultant working from frameworks
What this isn't
- A one-size-fits-all framework — your roadmap is built for your specific business, team, and goals
- Theory from someone who read a book — everything I advise, I’m doing in my own company right now
- A course or group program — this is 1:1 strategic advisory
This is for you if:
- You’re a founder or CEO at $1M+ revenue
- You run a business with a team — SaaS, services, media, e-commerce, or any company where AI is reshaping how work gets done
- You’ve bought some AI tools but nothing has stuck — no real transformation, just experiments
- You’re thinking about team restructuring but don’t know where to start
- You’re making decisions about team structure, hiring, and operations and want to get them right
- You want someone who runs a real business, not a consultant who’s never operated
The 90-day AI transformation roadmap
From “we know AI matters” to “we have a plan and we're executing.” Four phases, clear milestones, real accountability.
CEO Fluency
Weeks 1–4
Before you can lead a transformation, you need enough depth to be dangerous. You’ll build a personal AI stack you use daily, learn to evaluate tools, call BS on vendors, and develop the credibility to lead your team through what’s coming.
Milestone: You can articulate your company’s AI vision to your team with conviction — and demo something that blows their minds.
The Audit
Weeks 2–6
We map your entire business. Every role, every process, every SOP. Where is time being wasted? Where are the obvious automation wins vs. the ones that need more sophisticated tooling? We also find the political landmines — the people who’ll resist and the processes nobody fully understands.
Milestone: A complete operational map with every role tagged: keep as-is, augment with AI, consolidate, or eliminate.
The Roadmap
Weeks 4–8
We build the future-state org chart and the plan to get there. What does your company look like leaner? Which tools replace which roles? What’s the sequence — because you can’t cut everything at once. What do you tell the team? How do you handle the humans in this?
Milestone: A documented 6-month implementation plan with specific tools, timelines, team changes, and expected margin impact.
Implementation Support
Months 3–6+
Things will break. People will quit. Tools won’t work as expected. New AI capabilities will drop that change the plan. This is where you need someone in the trenches with you — adjusting the plan as reality hits, not handing you a binder and walking away.
Milestone: Measurable margin improvement and a team that’s operating in the new model.
Throughout the engagement you get
- Strategy calls — 2x 60-minute calls per month, recorded
- Async access — Slack or Voxer between calls, 24–48 hour response
- Direct access — no assistants, no gatekeepers
Why me
Still in the arena
I run Castos, a 7-figure ARR SaaS company. I took it from AI-skeptical to AI-native — leaner team, more profitable, runs better. I’m not advising from theory. I’m making these same decisions every week.
At your scale
Not $100M advice applied to your $3M business. I understand the constraints, the small teams, the wearing-multiple-hats reality.
Building in public
I publish everything I know and am learning on YouTube — so you can see how I think before we ever get on a call. Nothing I tell you is theoretical.
What founders say
I've leaned on Craig countless times when blocked or confronted with a particularly tricky fork in the road. More than once, a single call with him has translated into clear next steps. Because he's actively scaling Castos himself, his advice is grounded in real SaaS operator experience.
Craig is a great coach because he has literally been there and done that. He has the experience and the firsthand knowledge of building a business and he really helped me take a step back and evaluated where my business was and what it needed.
Craig is an outstanding coach who brings clarity and focus to every session. His thoughtful questions help me cut through the noise and leave each call with a clear action plan and renewed motivation.
How it works
Apply
Takes 2 minutes. Helps me understand your situation and determine fit.
Discovery call
30 minutes. I’ll be direct about whether this is the right fit.
Proposal
If there’s mutual fit, I’ll send scope, pricing, and start date.
Kickoff
90-minute deep dive to map your current state and build your roadmap.
3-month minimum commitment
Exact rate depends on your company's complexity and scope. We'll figure out the right number on the discovery call. For context — one wrong AI tool purchase or wasted implementation easily costs more than a full year of advisory.
I take on 5–7 advisory clients maximum. If you're reading this, there's likely a spot open. That won't always be the case.
Frequently asked questions
By end of month 1, you’ll have personal AI fluency and a complete operational audit of your business. By month 2, you’ll have a documented 6-month implementation plan with specific tools, timelines, team changes, and expected margin impact. Month 3 and beyond is execution support — adjusting the plan as reality hits. Most clients have a fundamentally different operating model within 6 months.
You don’t need to be. I translate AI capabilities into business strategy. You understand your business — I help you see where AI changes the math on your team, your costs, and your operations.
We start with CEO Fluency — getting you personally deep enough with AI to lead the transformation with credibility. In parallel, we audit your entire operation: every role, process, and SOP. Then we build the future-state org chart and a 6-month implementation plan. By the end of the 90-day intensive, you have a concrete roadmap and you’re already executing.
2 strategy calls per month plus async access via Slack or Voxer. Most clients use 2–3 hours of my time per week. You’re not buying hours — you’re buying access, expertise, and a plan.
Yes. For the right fit, I take on fractional and board-level advisory roles. We can discuss that on the discovery call if it makes sense for your situation.
Real transformation takes time. Month 1 is assessment and roadmap. Month 2 is implementation. Month 3 is when you see measurable results. Shorter engagements don’t give you enough runway to actually change how your company operates.
The companies that win the next 5 years are restructuring right now. The question is whether you have a guide.
Apply Now(opens in new tab)Takes 2 minutes. I review every application personally and respond within 48 hours.