Get your team proficient with AI in 90 days or less.
Chase leads your AI rollout: strategy, policy, team training and rollout, measured against your goals.
Start with the free AI assessment, about 10 minutes. Fractional from $6,000 CAD a month, 90-day minimum.
Have a question first? Text Chase at 778-999-0985, email, or connect on LinkedIn.
Sidekick has prepared the context, recommendation, and next move for each one.
First you, then your leadership team, then the rollout.
First you, one-on-one, until AI is part of how you work. Then your leadership team. Then the rollout, with baseline numbers set up front and progress reported against them. Chase handles the coordination across your leadership team, IT provider, vendors and partners, so it doesn't land on you or your team.
The assessment takes about 10 minutes. On the call we talk about where you are, what you want AI to do, and whether we're a fit.
Chase meets your leaders (up to six), shows AI working on your firm's own templates and past work (not client files), and presents what he found to your leadership team.
Measures agreed up front and reviewed every 30 days. You decide after each step.
Team training is run by Chase, with trusted partners for extra training capacity, and for IT and security work only when you don't have an IT provider.
If you're the one bringing this in
Your part: take the assessment, invite whoever approves to the 30-minute call, and help pick the first work and a few examples. Chase does the setup, the coaching and the reporting to your sponsor.
Need sign-off from your partners, board or boss? Send them the one-page summary.
Share the free AI assessment
About 5 minutes. Each person gets a report on where AI fits their own work, how to handle their data and what to do first. Nothing to buy.
Open the assessmentsidekickorchestration.ai/assessment
What it costs, and what it takes from your team.
One accountable partner to lead AI change across your business.
Most engagements run $6,000 to $12,000 CAD a month, depending on how many people we support and how fast you want to move. AI subscriptions are separate.
Your time: the executive sponsor, about an hour a week in month one; each leader, 30 minutes a week.
See the ownership scope
- →A roadmap of where AI fits, and where it doesn't
- →Your leaders and go-to people coached first
- →Managers and teams trained in groups
- →An AI-use policy and safe-use rules
- →Results reviewed against your baseline every 30 days
- →Coordination with your IT provider and any partners
Measures are agreed up front and reviewed every 30 days. If a milestone slips because of us, we keep working at no extra fee until it's delivered. You keep everything we build.
Book a 30-minute fit call →Want to move forward? Take the free AI assessment, about 10 minutes, then book a 30-minute fit call.
We are hiring and growing. For now, we take on a limited number of engagements at a time. If we are at capacity, we work with a network of trusted partners who can support clients who are unable to wait for the next available slot with Sidekick. What it takes from your team, step by step →
What you'll see, and when.
Before anything changes
How the work runs today and a baseline measure.
At each 30-day review
Which workflows are in use, by whom and how often, and what needed correcting.
By day 90
What changed in the measures you chose, what it cost to run, and a decision on what to scale and what to stop.
Illustrative 90-day plan for a 100-person firm.
No targets. Your plan, and who is involved when, is set in the first two weeks.
Days 1 to 30: you and your leaders
One-on-one coaching on each leader's own work. The staff AI-use policy is drafted. Baseline measures are set.
The baseline, and the first workflows in use by your leaders.
Led by: Chase
Days 31 to 60: your leadership team and managers
Small-group sessions. Each manager picks one team workflow to change first.
Which workflows are in use, by whom and how often.
Led by: Chase
Days 61 to 90: your teams
Hands-on workshops on each team's own work, then group coaching. Your IT provider handles access and licences.
What changed in your measures, what it cost to run, and what to scale or stop.
Led by: Chase, with a training partner if the timeline needs more hands
What changed inside their businesses.
Proposals, call prep, client follow-up and client work: processes that changed inside each business, described by the people who run them.
Every setup is built in the organization’s own accounts, so the business keeps it and the next person can pick it up.
Most of these start with one person’s process, often the owner’s. Fractional takes the same approach with your leadership team first, then the rollout.
Recaps and follow-ups after full-day sessions arrive drafted in the coach’s voice, ready to review.
“I hate sending follow-up emails.”
Meetings, presentations, investment memos and financial models are prepared behind the scenes.
“It feels like you suddenly have an admin, an analyst, and a small team working behind the scenes.”
Preparing properly for a call: about 45 minutes down to about 5.
“It remembers. Twenty-five years of relationships, and it holds the ledger: who introduced whom, what I promised, what they said in their own words.”
His calls and training sessions now update Salesforce, compare carrier PDFs and draft follow-ups.
“I built an interactive dashboard with my company’s branding in two minutes. Commission structures, stages, all of it. Then I built an accounting folder that basically works like a bookkeeper.”
Two or three clients’ work gets prepped at once, ready for the owner to take it from there.
“I can load it with two or three clients’ work while I’m on someone else’s. It’s already prepping the work, and I jump in and take it from there. I almost have my own support system instead of needing someone else to support me.”
A client newsletter with market statistics, in about 20 minutes.
“I’ve always wanted to send newsletters with market statistics to my clients and I’ve never been able to tackle it.”
Figures are each client's own estimate.
See these stories on What AI Can DoWhere most companies start.
Sales is usually first. Your people keep the relationship, the price, and every word that gets sent.
Sales teams
Each morning, a short list of the right people to contact and why, a one-page brief before each call, and CRM notes drafted after. Running for Sidekick Orchestration, now being set up for an HR firm.
Usually firstClient-facing teams
Proposals and client updates from your own past work.A Metro Vancouver home builder’s proposal process: about 40 hours down to about 4.
ProposalsOperations
Requests, reporting and the paperwork behind them.
RequestsMorning sales desk
When you are ready to prospect, a short list of the right people to contact and why.You keep: Who you contact and what you send.
See the sales desk →Figures are each client's own estimate.
More systems we've built →How we handle your data
Accounts and access
- Your AI runs in your own accounts, inside tools your company approves, with rules for what never goes in.
- Chase never logs in to your systems or asks for your passwords.
- We work with your IT provider on every package.
Files and records
- Client files are used only if you ask for it, case by case.
- Insured for professional liability and cyber.
- You keep everything we set up.
- Nothing that identifies you is shared without your permission.
For law, accounting and advisory firms.
Your clients trust you with their information, and your law society, professional body or regulator expects you to know how it is handled. So the work starts with what AI can see, and who checks it.
Client files stay out unless you ask
We start on your firm's own templates and past work. Client files are used only if you ask for it, case by case.
No logins, no passwords
Chase never logs in to your systems or asks for your passwords. Your IT provider or your team switches things on.
Your compliance lead sees it first
Your compliance lead sees what each tool can read before anything touches client matters. What a connection can do is set by its permissions, so we start read-only where possible.
A policy for how people use AI today
Solo for Execs gives the managing partner a staff AI-use policy that covers how people use AI today.
Tools: Microsoft Copilot, ChatGPT or Claude, chosen for your work and security needs, in accounts your business owns.
Chase founded Sidekick after more than a decade in B2B partnerships and revenue operations at SaaS, marketplace, and healthcare-data companies. Jobber. DoorDash. DrugBank.
The thesis is straightforward. Most owner-operated and mid-market firms cannot justify a full-time Head of AI yet. The fractional model is the bridge. Built right, it sunsets once the team is running the system without him.
Based in Metro Vancouver, BC. Selectively taking new engagements.
What buyers ask before signing.
Who is this for?
We tried AI before and it didn't stick. Why would this be different?
Can we keep using what's built if we stop?
Which tools do you support?
Is Fractional right for us, or Solo for a few people?
Can we stop partway through?
Not a fit: teams that need a full-time AI lead, or leaders who aren't convinced AI is for them.
Bring your leadership team's AI question.
The free AI assessment takes about 10 minutes. Then a 30-minute call: you leave knowing whether Solo, Solo for Execs or Fractional fits, or whether none does.
Start the free AI assessment →Send a note or book a 30-minute call. No preparation needed.
Have a question first? Text Chase at 778-999-0985, email, or connect on LinkedIn.
Looking for AI in your own work instead? See Solo and Solo for Execs. →