Sidekick Orchestration
// For wealth, advisory and insurance firms in Canada

Know where AI fits your business,and where it doesn’t.

Your advisors want the hours AI can give back. Your compliance team wants to know where client data goes, who checks the output and what stays on file. We help your firm get both, in the tools you already use.

Book a 30-minute fit call

Referred by someone you trust? Mention them when you book.

Have a question first? Text Chase at 778-999-0985 or email chase@sidekickorchestration.ai.

  • Wealth and advisory firms
  • Portfolio managers
  • Mutual fund dealers
  • MGAs
  • Insurers

15+ businesses and teams have worked with Sidekick.

Founder-led from Metro Vancouver.

// What changes

Less time on the back office.More time with clients.

Common problems for advisors and financial firms, and what AI can take on, with a person reviewing anything that reaches a client.

The problemWhat changes

Meeting prep, notes and follow-ups take hours that should go to clients.

More time with clients. AI prepares a brief before each meeting from your CRM, email and calendar, drafts the follow-up after it, and updates the record.

Nathan’s call prep: about 45 minutes down to about 5.

Client information is spread across the CRM, email, documents and personal notes.

More from the clients you already have. AI pulls each client’s history together and flags upcoming reviews, renewals and the next useful conversation.

Key processes live in a few people’s heads, so work stalls when they’re away.

A firm that doesn’t depend on one person. We write down how the work really gets done, so the same steps guide your people, the AI and anyone new.

Every client message carries risk, and manual copying invites mistakes.

Fewer errors, cleaner records. AI drafts and files from your own information; a person checks the recipient and the content before anything reaches a client.

Growth, new clients and acquired books add work faster than you can hire.

Faster onboarding. AI compares incoming client records with your way of working, inside your own accounts, and lists the gaps for a person to resolve.

People already use AI on their own, with no firm rules.

A contained, safe start. One or two low-risk tasks, written rules, a named reviewer, and a written record if your compliance lead wants one.

Not sure which of these fit your firm? Book a 30-minute fit call

// From client work

Prepared work,reviewed by a person.

Results are reported by the client. We have not measured them independently.

Nathan ParkhouseFounder, Nathan Parkhouse Advisory
“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.”

Pre-call briefs are built from his files, calendar and recent emails. By Nathan’s estimate, preparing properly for a call went from about 45 minutes to about five minutes of reading.

About 45 minutesabout 5to prepare properly for a call

Files, calendar and emailPre-call briefNathan reads
Aman GrewalManaging partner
“It feels like you suddenly have an admin, an analyst, and a small team working behind the scenes.”

An AI workspace helps plan the day, prepare meetings, and draft presentations, investment memos, and financial models.

Research and contextAnalysis and draft workAman decides
Kevin ChaputInsurance advisor, Bloom Benefits
“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.”

Training sessions and client calls feed into Solo, which updates Salesforce, compares carrier PDFs to the client’s situation, and drafts follow-up emails in his voice.

Calls and trainingUpdates and draftsKevin reviews
Read more client feedback
Chase Bernier, founder of Sidekick Orchestration
// Who you work with

You work directly with Chase Bernier, Sidekick’s founder.

Chase leads every engagement from the first call through setup and handover. Before Sidekick, he sold financial planning software to advisors at Planswell. Sidekick’s first client was an insurance advisor, and Chase runs his own company on AI.

More than a decade in B2B partnerships and revenue operations, including roles at Jobber, DoorDash and DrugBank. Based in Metro Vancouver, BC.

  • Insured for professional liability and cyber
  • Never logs in to your systems
  • Your data rules in writing before anything connects
  • You keep everything we set up
// How we work

Start small and safe.Expand what works.

We implement AI in stages. Each stage has an agreed scope and measures, and nothing expands without your sign-off. The written procedures stay with your firm.

  1. A 30-minute fit call.

    You tell us how the firm works and what you want from AI. We tell you plainly where AI fits and whether we can help.

  2. Discovery with your people.

    We talk to people in each role, then play back the pain points in their own words. Your team confirms we heard it right.

  3. Start small and safe.

    We pick one or two low-risk, high-impact tasks, such as meeting prep or follow-ups, and measure how long they take today.

  4. We write the procedures.

    You explain how the work happens. We turn it into written steps that guide both your people and the AI. No data clean-up project first.

  5. Measure, then expand.

    Leaders first, then the team. We coach people to use it well and safely, report results against the starting numbers, and expand only what works.

// Client data

How we handle client data.Agreed in writing first.

  • We never log in to your systems.

    Your team or your IT provider makes every change, and we coach them through it. We don’t ask for passwords or admin access.

  • We don’t take your client files.

    The AI works inside your own accounts. Sidekick works on how the work gets done, and handles sensitive client information only if you ask, agreed case by case.

  • Business accounts, in tools you already use.

    Usually Microsoft 365 Copilot, or a business plan of ChatGPT or Claude connected to your accounts. The provider’s terms govern where data is stored. We read them with you before anything connects.

  • Access is set out in writing.

    Access and data handling are set out in the written scope before work starts. It names what the AI can see, what it can do, and who approves each connection.

  • Safety rules from day one.

    Every setup includes written rules in the AI’s settings: what never goes into a draft, and what a person reviews before it reaches a client. These rules reduce risk. They don’t remove it.

  • Your compliance team decides.

    We set things up to fit your policies. If your compliance lead, dealer or MGA wants it in writing, we write up the setup: what the AI can see, what it can do, who reviews, and where final versions are saved.

    See a sample setup record

We work in the AI tools your firm already approves, usually Microsoft 365 Copilot or a business plan of ChatGPT or Claude. We are not tied to any of them.

// Three layers of control

No single control is enough. Together they back each other up.

  1. What’s in the systemConnect only the data the work needs.
  2. What the AI can doLimit each connection. AI drafts, a person sends.
  3. What people followWritten rules and a named reviewer.

More access makes AI more useful and widens what can go wrong. We help you choose that trade-off on purpose.

This describes how Sidekick works. It is not legal or compliance advice.
// What the rules say

The guidance already covers AI.Here’s where to read it.

The guidance so far applies the rules you already follow to work done with AI. Each summary below is our plain-language reading. Read the source, and check with your compliance team.

Canadian Securities Administrators (CSA) · December 5, 2024

CSA Staff Notice and Consultation 11‑348: Applicability of Canadian Securities Laws and the Use of Artificial Intelligence Systems in Capital Markets

Securities law is technology-neutral. Registrants stay responsible for their advice and recommendations, whether or not AI helps. CSA staff expect AI policies, human oversight, outputs that can be explained, proper records, and oversight of outside AI providers.

Applies to: Registered dealers, advisers and portfolio managers.

Read the source (opens in a new tab)

Privacy Commissioner of Canada and provincial regulators · December 7, 2023

Principles for responsible, trustworthy and privacy-protective generative AI technologies

Use de-identified information in prompts where you reasonably can. Enter personal or sensitive information only where you are authorized to. Tell people when they are dealing with a generative AI tool.

Applies to: Any firm that handles personal information.

Read the source (opens in a new tab)

CIRO · February 17, 2026

CIRO Compliance Report for 2026: Helping Dealers with Compliance

CIRO says its examinations will review how dealers use AI and the controls that check it works as designed. Dealers should understand and document their AI use across the business.

Applies to: CIRO investment dealers and mutual fund dealers.

Read the source (opens in a new tab)

CCIR and CISRO · 2018

Guidance: Conduct of Insurance Business and Fair Treatment of Customers

Sets the conduct expected of insurers and intermediaries, from product design to claims. It predates generative AI. Our reading: the fair treatment standard applies to advice and client messages however they were drafted.

Applies to: Insurers and intermediaries, through your provincial regulator.

Read the source (opens in a new tab)

Not legal adviceThese are plain-language summaries, checked September 28, 2026. Your dealer, MGA or regulator may set stricter rules, and those come first.

// Read before your call

Free resourcesfor financial services firms.

// Free resource

Advisor AI use map

Where you can and can’t use AI, with sources.

Open the use map
// How we work with firms

Leaders first.Then the team.

For a firm, the usual first step is the free AI assessment, then a fit call.
What you keep: everything we set up.

For the firmUsual first step

Free AI assessment

Free

See where AI could help your firm, on your own time. Then a free 30-minute fit call with Chase.

Self-serve and online. The fit call tells you whether Fractional fits.

Take the free AI assessment
For the firm

Fractional AI Leadership

Starting from $6,000 CAD / month

Get your team proficient with AI in 90 days or less. For teams ready to run on it.

90-day minimum. In the first two weeks, Chase meets your leaders (up to six) and presents what he found. Then managers and rollout, with measures agreed up front.

For companies
For one advisor

Sidekick Solo

CAD 1,800 per person

Get proficient with AI in 30 days or less.

For one person who wants their own work set up first.

About Solo
// Good to know

Questions principals ask first.

Plain answers. Not legal advice.

Our dealer or MGA decides which tools we can use. Can we still do this?

Yes. We start with what they already allow. If they want it in writing, you get a setup record to share with them before anything connects. Not legal advice.

Can we put client information into AI?

Often yes, on a business account with the right settings and inside your policies. Where you reasonably can, leave identifying details out. We set written rules for what never goes into a prompt or a draft, and a person reviews anything that reaches a client.

Will this pass our compliance review?

We can’t approve anything, and we won’t claim to. We can document the setup, the data rules and the review steps so your compliance lead, dealer or MGA can review them against their own rules. You can see a sample setup record before the call. Not legal advice.

Are AI drafts part of our records?

That depends on your regulator and your policies, so your compliance team decides. We set up the process so the final, reviewed version is saved where your records already live. Not legal advice.

Do we need to clean up our data or replace our CRM first?

No. We start with how the work happens today and the tools you already have. Cleaner records and written procedures come out of the work.

Is our data used to train AI models?

On business plans, the major providers say they don’t train on your data by default. We check the current terms of your plan with you before anything connects.

Will AI make our service feel less personal?

The aim is the opposite. Less time on data entry, chasing and re-reading email threads means more time with clients. Your people keep the relationships and the judgment.

What if the AI gets something wrong?

Sometimes it will. That’s why a person reviews anything that reaches a client, and why the rules are written down. When something slips through, we add a rule so it doesn’t happen again.

Will this work with our CRM, dealer platform or agency system?

We don’t specialize in any one financial-services system. We work with what your AI tools can connect to, such as email, calendar, documents and many CRMs, and we tell you early if a system can’t connect.

Do you carry insurance?

Yes. Sidekick carries professional liability (errors and omissions) and cyber liability insurance. We can share a certificate of insurance on request.

What do you keep from our calls?

Notes from our calls go into Sidekick’s client records. Recording is optional and only with your permission. If you prefer, we take handwritten notes only, and those go into the same records.

// Next step

Bring the question your compliance team keeps asking.

  • Tell Chase how your firm works today and what you want from AI.
  • Hear where AI fits, where it doesn’t, and what is safe to start with.
  • Leave with a next step, whether that’s with us or not.
Book a 30-minute fit call

Have a question first? Text Chase at 778-999-0985 or email chase@sidekickorchestration.ai.

Referred by an advisor or consultant you trust? Mention them when you book.