Common questions.
Clear answers about Sidekick Solo and Fractional Chief AI Officer before you decide what fits.
Fractional Chief AI Officer
12 questionsWhat does a Fractional engagement cost?
Ongoing Fractional Chief AI Officer engagements start at $3,000 CAD per month with a 90-day minimum. An organization can also begin with one measured workflow when the problem, sponsor, and evidence are clearly bounded. That starting scope and price are confirmed after qualification. Any specialist technical delivery is scoped separately when the workflow and operating requirements justify it.
What is Fractional Chief AI Officer?
A Fractional Chief AI Officer is an accountable operator for how AI enters the organization. Sidekick helps choose the workflows worth changing, implements the first useful changes, and establishes controls, adoption, measurement, and ownership around them.
An organization can start with one measured workflow or use ongoing Fractional ownership when several teams, systems, or delivery partners need coordination. Your team keeps the workflows, operating context, controls, and decision record.
Who is this for?
Fractional is for organizations where AI use is spreading without shared priorities, controls, or ownership. The best fit has an accountable executive sponsor, one or more real workflows to improve, and people who can help define the current process and review the result. You do not need a large technical team. You do need an owner for the business decision and access to the people who run the work.
We've tried AI before and it didn't stick. Why would this be different?
We begin with the current workflow, what already exists, and the reason earlier attempts did not hold. Then we define the result, boundary, owner, and review process before changing the tools.
The first change stays small enough to test in real work. We record what passed, what needed correction, and what the evidence supports next. Useful parts of the existing setup stay. Weak parts are improved or stopped instead of being scaled by default.
What does the engagement look like: timeline and commitment?
We start with a fit conversation about the work, sponsor, current process, and main constraint. A bounded organization can begin with one measured workflow: establish the baseline, build the smallest useful change, review it with real users, and decide whether to hand off, improve, expand, hold, or stop.
Ongoing Fractional is a monthly engagement for organizations where several workflows, teams, controls, systems, or delivery partners need one operating owner. Every engagement has a defined scope, decision rights, and transfer path.
Do we have to start with one measured workflow?
No. A measured workflow is a sensible bounded start when the organization needs evidence or a contained first step. You can enter ongoing Fractional ownership directly when the sponsor, workflow evidence, operating cadence, and decision rights are already in place.
Is the bounded start a workshop?
No. The team maps one real workflow, configures and tests the smallest useful change, uses it on approved cases, and leaves with a runbook and an evidence-based next decision.
Do you replace our existing tools?
Usually not. We start with the workflow and the systems already involved, then choose the smallest platform change that fits the work, risk, access, and review requirements. A new subscription or specialist integration is added only when the operating need justifies it.
What does human-in-the-loop actually mean in practice?
It means the workflow names which actions AI may prepare, which actions a person must review, and which decisions remain fully human. The review boundary depends on the data, impact, reversibility, and client policy. Consequential sends, commitments, account changes, and production actions stay behind explicit approval unless the client has separately designed and authorized a different control.
How do you handle our data?
Your data stays yours. Data handling is defined before we build, with work performed in client-controlled accounts and tools wherever practical. Any data sent to an AI provider or connector follows the permissions, plan, and settings you approve. Sidekick does not use client data for model training. Provider training and retention terms depend on the service and plan you choose, and that boundary is documented before launch.
Do we need a technical team to work with you?
Not for every engagement. We need an accountable sponsor and people who understand the workflow. Technical, security, data, or system owners join when the work touches their responsibilities. Specialist implementation is scoped separately when the operating requirement needs it.
What happens when the engagement ends?
Your team keeps the delivered workflows, operating context, controls, documentation, and decision record, subject to the agreed licences and third-party platform terms. The engagement ends through a defined handoff or continues only through a separately agreed scope. Sidekick does not make ongoing dependence a condition of using what was delivered.
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
14 questionsWhat'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 $1,200 you get the full done-for-you setup, a 30-minute onboarding session, and seven days of support; Solo + Coaching at $1,800 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?
The result varies with the work, source quality, review burden, and how consistently you use the workspace. Solo does not promise a fixed number of hours or a guaranteed return.
The first goal is dependable use: the workspace starts with your context, recurring work, and review preferences instead of a blank chat. During onboarding and the refinement window, you learn how to brief it, check the result, and adjust the workflow.
A useful Solo workflow should make a recurring task easier to prepare or review without lowering the quality you need. Use your own before state to judge whether it helped.
Can't I just set up Claude myself?
You can. Solo is for people who want the workspace configured around their role, priorities, communication style, recurring decisions, and review preferences. The value is the connected context and operating structure, plus onboarding and a refinement window, rather than a single prompt or template.
How much does Sidekick Solo cost?
Solo comes in two tiers, both one-time. Sidekick Solo is $1,200 CAD: the full done-for-you setup, a 30-minute onboarding session, and seven days of support. Solo + Coaching is $1,800 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. Choose the plan that fits your workload; for sustained Solo use, we recommend Max 5x at $100 USD/month as the practical starting point. Lighter users can begin on Pro, and heavier daily users can choose Max 20x. Claude bills separately and can change its pricing and limits. There is no ongoing Sidekick subscription or proprietary Sidekick runtime.
Can I buy Solo for several employees?
Sometimes, when each person needs an independent workspace and no shared operating change is involved. We qualify the use case first. Shared workflows, team rules, and ongoing ownership belong in Fractional. If several people need to change how they work together, start there instead.
How long does setup take?
The workspace is built and configured before delivery. Once it is ready, opening it in your Claude account and starting your first session takes only a few minutes. A 30-minute onboarding session is included with every Solo delivery so Chase can walk you through the system and answer questions. The $1,800 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 can use the Claude plan that fits your workload and judgment. For sustained Solo use, we recommend Max 5x as the practical starting point because it provides substantially more capacity than Pro. Lighter users can begin on Pro, and heavier daily users can choose Max 20x. Anthropic bills the subscription separately, and its prices, usage limits, data settings, and terms can change.
Is my data private?
Your Solo workspace runs in your own Claude account. Sidekick does not have ongoing access to your live Claude sessions or account after delivery unless you explicitly share something for support. Claude is a cloud service, and Anthropic's training, retention, and privacy treatment depends on the plan and settings you choose. Review those settings against the sensitivity of your work. Sidekick does not use your client content for model training or sell it to third parties.
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 does not fit how you work, we review the mismatch and adjust the instructions, output format, or approved context where appropriate. The goal is a workspace you can use and review confidently.
Why does a Cowork session take longer than a regular Claude chat?
A Cowork session can read approved files, use configured tools, and build an output across several steps. That usually takes longer than producing one chat response. The right comparison is whether the finished work is useful and reviewable, not whether every response is instant.
What if I want more help after I'm set up?
Bring the next outcome to Chase. Additional support or work is scoped separately only when the need, owner, boundary, and expected result are clear.
What if I start with Solo and later want a Fractional Chief AI Officer engagement?
Solo and Fractional solve the same operating problem at different scales. A future Fractional engagement can reuse relevant personal context and working patterns when the organization has a shared workflow, accountable sponsor, and appropriate access. Contact Chase to discuss the organization-level need.
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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