How working with us works

Most leaders we talk to ask the same things before they bring in help with AI. Will this work for a business like ours? How much of my time will it take? What happens to our data? How will we know it worked? Here are our answers.

Is this a fit for us?

We work with owners and leaders of growing service firms, about 20 to 300 people, and with individuals who want their own AI set up.

You are a good fit when:

• You believe AI is worth it and want it working in your business.
• You have clear goals you want to reach faster.
• Your time, or your leaders' time, is the bottleneck.
• You are willing to change how you personally work.
• The person who makes the final decision takes part in the work.

We are not the right help when:

• You are still deciding whether AI is worth it at all. We are most useful once you have decided it is. Start with the free AI Opportunity Map; it shows where AI could help in your week in about ten minutes.
• There is no goal to speed up. Without one, nobody can tell whether it worked.
• You want staff trained before your leaders use it. Without leaders who use it themselves, a rollout stalls in competing opinions.
• You need a full-time AI lead. We will say so and help you hire one.

Solo or Fractional?

Solo is for one person, such as an owner or a leader, who wants AI handling some of their recurring tasks. Want a few key people set up too? Each person is their own Solo, at $1,800 CAD per person. That is also a smaller way to start: Solo for the owner and one or two leaders, then decide about the company.

A leader who also has to answer the board, partners or staff can take Solo for Execs ($2,900 CAD once): Solo plus an AI position brief, a staff AI-use policy, talking points and a personal 90-day plan.

Your Solo setup arrives within 48 hours of your payment, and coaching then runs for 30 days. You switch it on with a short guide, or your IT provider does, so Chase never needs your passwords.

Fractional is for a company that wants AI across a team, a department or the whole business. It always starts with your leaders, because they set the priorities and the budget.

What gets set up

Everything is built around work you already do, from your own templates and past work:

• For a leader: replies drafted in your voice, a brief waiting before each meeting, decisions prepared with the facts in one place.
• For sales: call prep, follow-up drafts ready on time, CRM notes, proposal drafts built from your past proposals.
• For a professional firm: client replies, engagement letters and monthly reports drafted from your own templates.
• For an owner who runs the office too: a quote drafted from your site notes, answers to common client questions, recurring reports.

You review anything before it goes to a client.

Where do we start, and how do we find the bottlenecks?

We start with your week. Where does the leader's time go? What work repeats? What waits on one person before it can move? Then we rank those against your goals.

1. The free AI Opportunity Map. About ten minutes. You rank your priorities and get your map straight away. Get your AI Opportunity Map.
2. The fit call. Thirty minutes on your work and what you want from AI. You leave knowing which option fits and what it would take.
3. For Fractional, the first two weeks of the engagement. 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. Then you get a 90-day plan with measures agreed up front.

Who do we work with in your company?

• Your leaders first. They learn to use AI in their daily work and set a written AI strategy and policy you can take to your board.
• Then your managers, so they can lead AI use in their teams.
• Then your teams, with training and rollout across departments or the whole company. When several teams need training at the same time, we bring in a vetted workshop trainer. That work is quoted before it starts and billed by Sidekick on top of the monthly fee.
• Your IT provider. We talk with them directly or send a checklist, your choice. They make any account changes. We never log in to your systems or ask for passwords.
• One person on your side who owns it day to day, about an hour a week checking results, collecting corrections and answering colleagues' questions, so it keeps running after us.

Asked to look into AI for your company? Get your free AI Opportunity Map, send the owner this page with your map, and invite them to the fit call.

What does it take from you?

For Solo:

• Examples of the work that fills your week, if you have them. Templates and past work with client names removed are fine.
• About 3 hours over the month: a 30-minute onboarding call and four 30-minute calls with Chase, ideally one a week, plus email or text to Chase between calls for 30 days. Calls can move around your week.
• Using it on your real tasks between calls. That is what makes it stick. If AI has not stuck for you before, here is why it usually stalls.

For Fractional:

• An executive who leads it on your side and uses it themselves.
• About 4 hours from that executive in the first two weeks, and 45 minutes each from other leaders. After that, each person's time is set in the 90-day plan.
• Starting numbers for the measures, or time with us to set them.
• One person who owns it day to day, about an hour a week checking results, collecting corrections and answering colleagues' questions.
• Quick decisions when we need them, and access approved by your IT provider.

We do the building, testing, documentation and coordination between meetings.

What does success look like, and when?

• Solo: proficient in 30 days, meaning you give AI work every week without us.
• Fractional: by day 90 your leaders are proficient, you have a written AI policy and plan, and the measures you picked have moved against where you started.
• Measures come from goals you already track: how long proposals take, how many follow-ups go out on time, how much leader time goes into preparation.
• On Fractional we review the measures with you every 30 days. Thirty days is usually too early to see a number move, so we judge results at 90 days.
• On Fractional, if a milestone slips because of us, we keep working at no extra fee until it is delivered. If a slip is on your side, we say so plainly and reset the plan.

What does it cost, and what do you keep?

• Solo: $1,800 CAD, once. You pay the AI provider (Microsoft Copilot, ChatGPT or Claude) directly.
• Fractional: from $6,000 CAD a month. Most engagements run $6,000 to $12,000 CAD a month, with a 90-day minimum. The price depends on how many people we support and how fast you want to move. The first 90 days are a firm commitment. At day 90 you decide whether to continue, change the scope or stop.
• You keep everything we build. It stays in your business account after we finish.

Your data, your IT provider and which AI tool

We agree data handling in writing before we build, including what stays out. We do not take sensitive client data unless you ask, and then we agree it case by case. Accounting, engineering and law firms: tell us on the fit call what your professional duties cover. What the AI provider may keep depends on the plan you choose, and we write that down with you. We are happy to sign your NDA.

Read: AI and sensitive information: a few settings and a few decisions

Which tool? We recommend the one that fits your work, your data and what you already pay for. Microsoft 365 businesses often start with Copilot.

Read: Copilot vs ChatGPT vs Claude: which is safer?

Who you will work with

Chase Bernier, founder. He leads every engagement and is your single point of contact. He runs Sidekick on AI (here is what it handles) and has set up AI for more than 15 businesses and teams. Before founding Sidekick Orchestration, he spent his career on the business side of new technology: turning around a market at DoorDash, building the partnerships division at DrugBank, and, at Jobber, seeing inside a couple of thousand small service businesses as they moved from paper to software, which showed him where change stalls.

Sidekick takes on at most four Fractional clients at a time, so Chase can lead each one. If we are full, or the work is outside what we do, we tell you and suggest someone who fits.

Not ready to talk yet? Get your free AI Opportunity Map first, about ten minutes.

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