Question 1

What's the difference between Sidekick Solo and Fractional AI Officer?

Accepted Answer

The difference is what gets equipped, and from which direction. Sidekick Solo equips an individual: we build one person their own AI workspace, configured around their role, and coach them to run on it. One-time, $1,800 CAD. It works for anyone, an independent professional, a business owner, or a leader inside a large company, and an organization can put its people on Solo one by one. That is adoption from the bottom up. Fractional AI Officer equips the organization itself: Chase embeds in your business, builds AI into how the operation runs, and trains your team to run it without him. From $3,000 CAD per month. That is adoption from the top down. The two work together. Many clients start with Solo and expand into a Fractional engagement, and Fractional engagements can include Solo setups for key people.

Question 2

What's included in Sidekick Solo?

Accepted Answer

A configured skill system covering strategic thinking, communications, meeting intelligence, and operations. Done-for-you setup built around your specific role and context. Seven days of direct 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 also includes four weekly coaching sessions and async messaging through your first month, so you have someone in your corner while you build confidence.

Question 3

Can't I just set up Claude myself?

Accepted Answer

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 100+ 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.

Question 4

How much does Sidekick Solo cost?

Accepted Answer

$1,800, one-time. That includes the full done-for-you setup plus four weekly 30-minute coaching sessions with Chase, async messaging between sessions, and hands-on support through your first month. You also need your own Claude subscription: the $20 USD/month Claude Pro plan is the minimum, though we recommend the $100 USD/month Claude Max plan, since real daily use almost always hits the limits on the lower one. We walk you through this on the call. You pay once for Solo and the workspace is yours.

Question 5

Do you offer volume or bundle pricing?

Accepted Answer

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 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.

Question 6

How long does setup take?

Accepted Answer

Setup takes about five minutes. You receive your configured workspace and start using it right away. A 30-minute onboarding walkthrough is included with every Solo delivery so Chase can walk you through the system and answer questions. Solo also includes four weekly 30-minute coaching sessions over your first month, plus async messaging between sessions.

Question 7

Do I need any technical skills?

Accepted Answer

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.

Question 8

What is a skill?

Accepted Answer

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.

Question 9

What Claude plan do I need for Sidekick Solo?

Accepted Answer

The $20 USD/month Claude Pro plan is the minimum. We recommend the $100 USD/month Claude Max plan: across our clients so far, real daily use has consistently hit the Pro plan's usage limits. If you are not hitting your plan's limits, you are likely not using this enough to get the return.

Question 10

Is my data private?

Accepted Answer

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.

Question 11

What if Solo doesn't work for me?

Accepted Answer

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.

Question 12

Why does a Cowork session take longer than a regular Claude chat?

Accepted Answer

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. Sessions take longer because they are 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.

Question 13

What if I want more help after I'm set up?

Accepted Answer

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.

Question 14

What if I start with Solo and later want a Fractional engagement?

Accepted Answer

They are designed to work together. Clients who start with Solo and move into a Fractional engagement build on the foundation they have already established. The context you build in Solo (your workflows, your communication style, your decision patterns) becomes the starting point for a broader engagement, not something you rebuild from scratch.

Question 15

What is Fractional AI Officer?

Accepted Answer

Fractional AI Officer is an embedded AI operations leadership engagement for owner-operators and operations leaders. Chase works inside your business as your fractional AI ops lead, building workflows, coaching your team, and architecting the AI operations layer your business runs on. Three tiers: Pilot ($3,000 CAD per month), Build ($6,000 CAD per month), Operate ($12,000 CAD per month). Three-month minimum commitment, then six-month renewals. Built to sunset once your team can run the system on its own.

Question 16

What does Fractional AI Officer include at each tier?

Accepted Answer

All three tiers include AI operations strategy, workflow design and build, leadership coaching, a team knowledge library, and async support. Pilot ($3,000 per month) is the entry-tier engagement: focused workflows, light coaching, team-ready recipes. Build ($6,000 per month) adds multi-team workflows plus culture and adoption strategy. Operate ($12,000 per month) is AI as the operating layer: cross-functional architecture with a shared knowledge layer and multiple working sessions per week.

Question 17

What counts as a partner-routed build?

Accepted Answer

Custom multi-agent deployments (Managed Agents architecture, bespoke MCP servers, API-direct integrations) sit outside the Fractional engagement. Cost is determined by partner and scope, ranging from low 5 to low 6 figures. Sidekick has multiple implementation partners for that work depending on your requirements and base infrastructure. Chase scopes and oversees; you own the output. This is different from Fractional engagement work, which is strategy, coaching, and workflow design delivered by Chase directly.

Question 18

We've tried AI before and it didn't stick. Why would this be different?

Accepted Answer

Most AI projects fail because they ask your team to learn a new tool and change how they work. Sidekick Orchestration inverts this. We map your existing workflows first, then build AI workflows to fit them. Your team does not learn a new tool. They just do less of the repetitive parts of their current job.

Question 19

What does the engagement look like: timeline and commitment?

Accepted Answer

Every engagement starts with a free 30-minute intro call. From there, the three-month minimum begins: Chase maps your workflows, ships the first ones into production, and embeds with your team. After three months, you can continue with six-month renewals or wind down. The engagement is built to sunset once your team can run the system on its own.

Question 20

Do you replace our existing tools?

Accepted Answer

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 goal is fewer manual steps, not a rip-and-replace.

Question 21

What does human-in-the-loop actually mean in practice?

Accepted Answer

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.

Question 22

How do you handle our data?

Accepted Answer

Your data stays yours. We implement strict protocols ensuring no sensitive information is used to train external AI models. Read/write access is granular: we touch only what the workflow requires, and nothing more.

Question 23

Do we need a technical team to work with you?

Accepted Answer

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.