Common questions.
Everything you need to know about Solo and Fractional Chief AI Officer before booking a call.
Fractional Chief AI Officer
What is Fractional Chief AI Officer?
A Fractional Chief AI Officer is an embedded engagement where Chase works inside your organization to build AI into how you actually operate. Not a workshop. Not a report of recommendations. A real implementation: we map your workflows, identify where AI creates the most leverage, and build the infrastructure that makes it stick.
The difference from a consultant is the depth. Chase is not advising from the outside. He is inside the operations long enough to see where the real friction is, and building solutions that do not require you to maintain them indefinitely after he is gone. Three tiers: Pilot ($3,000 CAD per month), Build ($6,000 CAD per month), Operate ($12,000 CAD per month).
Who is this for?
Owner-led businesses and SMBs with five to one hundred employees where leadership is trying to figure out AI before the competition does. Typically the founder or CEO has seen AI ROI projections, maybe bought some subscriptions, and six months later half the team has stopped using them. The Fractional Chief AI Officer engagement is designed for organizations where the intent is there but the implementation has stalled. You do not need a big IT budget or a technical team. You need someone who understands both the technology and how a small business actually runs.
We've tried AI before and it didn't stick. Why would this be different?
Most AI projects fail because they ask your team to learn a new tool and change how they work at the same time. This engagement inverts that. We map your existing workflows first, then build AI to fit them. Your team does not learn a new tool. They just do less of the repetitive parts of their current job.
The engagement does not start over from scratch either. It starts from an honest assessment of what is there: what is working, what was never going to work, and what is worth keeping. You do not lose the investment in what you have already tried. The difference from a consultant is the depth: Chase is not advising from the outside. He is inside the operations long enough to see where the real friction is, and building solutions that do not require you to maintain them indefinitely after the engagement ends.
What does the engagement look like: timeline and commitment?
Every engagement starts with a free 30-minute intro call. From there, three phases: Pilot, Build, and Operate. Pilot is the diagnostic and first build. We map your current state, identify the highest-value entry points, and ship one or two working workflows your team can use immediately. Build is the infrastructure phase. We go deeper, add integrations, and build out the use cases that create real leverage for your operations. Operate is the ongoing layer. The workflows are running, and we tune them over time as your business changes.
Each phase has a defined scope and deliverables. Nothing is open-ended. Pilot runs for a defined window, usually four to six weeks, and gives you something working quickly. Build takes longer depending on the complexity of your operations, typically two to four months. Operate is ongoing as long as the business wants embedded support. The three-month minimum applies, then six-month renewals or wind down. The engagement is built to sunset once your team can run the system on its own.
Do you replace our existing tools?
No. Sidekick Orchestration builds AI workflows around your current stack. We connect to what you already use: your CRM, your email tools, your project management software, and build workflows that run on top of them. The only new subscription is Claude for your team. The goal is fewer manual steps, not a rip-and-replace.
What does human-in-the-loop actually mean in practice?
It means nothing executes without your team approving it first. AI handles the research, drafting, and preparation. Your team reviews the output, makes any edits, and approves before anything gets sent or logged. We design this into every workflow from the start, not as an add-on.
How do you handle our data?
Your data stays yours. Operational data stays in your tenants. No training data flows back to Sidekick or to Anthropic for model training. The only data that crosses a boundary is what you authorize through your own tool permissions during workflow build.
Do we need a technical team to work with you?
No. One of our core requirements is that clients do not need to manage anything technical on their end. What we do need is someone who understands the workflows we are implementing: typically a manager or ops lead, not an engineer.
What happens when the engagement ends?
The infrastructure belongs to your organization. All workflows, integrations, documentation, and trained systems stay with you. You are not dependent on an ongoing subscription to a third-party platform that owns your data. After the engagement, clients who want continued support typically move to a lighter retainer: a few hours a month to tune, expand, and handle whatever the business brings next. That is optional, not a condition of the engagement.
Most Fractional engagements start after at least one failed rollout. Read what actually changed for five owners →
Ready to talk about your organization? The 30-minute call is the right next step.
Sidekick Solo
What's included in Sidekick Solo?
30+ configured skills covering strategic thinking, communications, meeting intelligence, and operations. Done-for-you setup built around your specific role and context. Seven days of direct email support from Chase. A refinement window to adjust anything that is not working the way you would expect. You receive a workspace that is ready to use from session one, not a template you configure yourself. Solo comes in two tiers: at $1,600 you get the full done-for-you setup, a 30-minute onboarding session, and seven days of support; Solo + Coaching at $2,200 adds four weekly 30-minute coaching sessions and async messaging through your first month, so you have someone in your corner while you build confidence.
How much time will this actually save me?
Setup compresses dramatically. Ongoing ROI builds with use. Week 1 is calibration, not payoff.
Think of it like a gym membership, except we set the gym up in your house, stocked it with the right equipment, and gave you a trainer for the first month. You still have to lift. The learning curve does not disappear. Sidekick compresses it from months of solo trial and error to a few weeks with a guide.
Setup is where the big compression happens. Without support, getting AI working in your business means months of figuring it out alone: bad outputs, no configuration done for you, no resources, no one to ask. With Sidekick, you are operational in days. Your workspace is built, your workflows are configured, your tools are in place.
Ongoing ROI grows as you build the habit. A follow-up email that used to take 30-40 minutes takes 5. Meeting prep that used to eat an hour is a quick review. By Month 2, clients stop thinking "Claude saves me time here" and start thinking "why did I ever do this manually?"
Week 1 is when you are learning how to give good instructions. Claude is brilliant but takes instructions literally. The better you get at briefing it, the better the output. That skill compounds, and it is the single biggest predictor of how fast the ROI arrives.
Can't I just set up Claude myself?
You can. Most professionals and business owners who find Sidekick Solo have already tried. The difference is between a general-purpose AI that starts from zero every session and a configured workspace that already knows your role, your priorities, your communication style, and the way you make decisions. The system behind Solo is 500+ sessions of iteration: context systems, voice calibration, decision history, and cross-skill integration where each piece references the others. The easy part is the first file. The hard part is everything that makes the system compound.
How much does Sidekick Solo cost?
Solo comes in two tiers, both one-time. Sidekick Solo is $1,600 CAD: the full done-for-you setup, a 30-minute onboarding session, and seven days of support. Solo + Coaching is $2,200 CAD: everything in Solo plus four weekly 30-minute coaching sessions with Chase and async messaging through your first month. You also need your own Claude subscription. For real daily use we point clients to the Claude Max plan: $100 USD/month for Max 5x is the realistic minimum, or $200 USD/month for Max 20x if you lean on it heavily. The $20 Pro plan is fine for trying it out but hits its limits fast. We walk you through this on the call. You pay once and the workspace is yours.
Do you offer volume or bundle pricing?
Yes. Solo seats are discounted progressively for three or more, so equipping a team gets more affordable per person as it grows. Separately, if you run both Solo and a Fractional Chief AI Officer engagement, Solo comes at a heavily reduced rate. To be clear, the two are independent. You can run either on its own, and most clients do. The discount is simply there for anyone who chooses both. Contact us for specifics on either.
How long does setup take?
Setup takes about five minutes. You receive your configured workspace and start using it right away. A 30-minute onboarding session is included with every Solo delivery so Chase can walk you through the system and answer questions. The $2,200 Solo + Coaching tier adds four weekly 30-minute coaching sessions over your first month plus async messaging between sessions.
Do I need any technical skills?
No. If you can use Claude, you can use Sidekick Solo. The setup requires nothing technical from you. You describe how you work and we build around it. After delivery, using the system is just opening Cowork and starting a session. Nothing to install, configure, or maintain.
What is a skill?
A skill is a pre-built workflow that runs inside your Claude workspace. Each one is configured to handle a specific kind of task: drafting follow-up emails, briefing you before a call, synthesizing your week, tracking commitments. You describe what you need and it handles the rest, already knowing your role, your voice, and your context.
What Claude plan do I need for Sidekick Solo?
You need at minimum Claude's Pro plan. If you are not hitting your plan's usage limits, you are likely not using this enough to get the ROI. If you run multiple long sessions each day, Claude Max removes the ceiling entirely. You can upgrade at claude.ai/settings.
Is my data private?
Yes. Your Solo workspace runs on your own Claude account. Sidekick Orchestration does not have access to your sessions, your files, or your conversations after delivery. Nothing you put into your workspace is used to train AI models or shared with anyone. Your context stays on your machine, in your account.
What if Solo doesn't work for me?
Every Solo delivery includes a refinement window and seven days of direct support from Chase. If a skill is not landing or a workflow does not fit how you actually work, we adjust it. Most refinements are small: a tone shift, a different output format, an added context source. The goal is a workspace you actually use, not one that looks impressive on delivery day.
Why does a Cowork session take longer than a regular Claude chat?
Cowork is not a chat interface. When you give it a task, it reads your files, runs specialized tools, and builds actual output, not a single generated response. A session that drafts your follow-up emails, consolidates action items across three recent calls, and surfaces two flagged client relationships is doing the work of an hour of focused attention. It takes longer because it is doing more.
The people who get the most out of Solo keep two or three sessions open at once and rotate between them. The wait disappears.
What if I want more help after I'm set up?
Ongoing support, project-based work, coaching, and group training are all available beyond your initial setup. Ask on the call and we will figure out what makes sense for where you are.
What if I start with Solo and later want a Fractional Chief AI Officer engagement?
These products are designed to work together. Clients who start with Solo and move into a Fractional Chief AI Officer engagement build on the foundation they have already established. Contact Chase to discuss what makes sense for your organization.
The fastest answer is a 30-minute call.
No pitch, no pressure. If it is not the right fit, we will tell you.
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