// Inside Sidekick · Updated 1 Oct 2026

How Sidekick runs on AI, and where Chase still decides.

Three real outputs, with names hidden where needed, and one labeled sample.

Chase Bernier founded Sidekick Orchestration and runs it on AI. This page shows what each system does, and the decision it leaves for him.

Book a free 30-minute call See the outputs

// How it runs

Something happens. The whole job runs. It stops at a decision.

Each system waits for a trigger: a call is booked, a call ends, Monday comes. Then it gathers the context, drafts, checks the details and hands back one decision.

SalesA first call is booked
A brief from the email thread, the invite, the introducer's notes and anything the prospect has published: what to ask, what not to pitch, and which facts it could not confirm.
Chase decides what to say.
SalesA call ends
The CRM update drafted from the meeting record and email: who, what was said, and the next step.
Chase checks it before it is saved.
DeliveryA fit call goes well
A proposal draft. AI reads it as four kinds of buyer would and lists their objections. The draft is fixed, then AI checks every claim against its source before Chase sees it.
Chase approves the exact file and sends it.
DeliveryA contract, tax or privacy question comes up
The question framed plainly and a short draft note to the lawyer.
Chase and his lawyer decide.
OperationsMonday comes
A three-line progress summary on this quarter's priorities, with the numbers behind it and any data it could not find.
Chase makes one change to that week's priorities.
WebsiteA visitor finishes the AI Opportunity Map questions
The AI Opportunity Map is a free questionnaire, about 10 minutes. The visitor gets a short written report on where AI fits their work, on screen and by email. Chase gets a notice.
If the visitor books a call, Chase holds it.

// The outputs

Four pieces, as they came out.

Three are excerpts of actual output. One is a sample map on a fictional firm, and it is labeled. Names are swapped for plain descriptions in brackets. Pick one to read it.

What started it: A Sunday check of every open item.
What it did: Checked 51 open items against email, calendar, the live website and records. Nothing was sent or changed.
Where Chase decided: About ten minutes of yes or no. That afternoon 9 items closed and 21 were parked, each with a date to come back. The 21 came from several park lines on the list; the excerpt shows one of them.

Real output · 27 Sep 2026 · excerpt, names hidden

Decision list, checked 27 Sep 2026

Yes or no (about 10 minutes, nearest deadline first)

[A partner] reply, due 29 Sep. The draft says “attached”, but no file is attached. Attach the notes, check the file, then you send? Yes or no.
[A prospect] said not now. Close it as dormant? Yes or no.
Park the 11 items outside this quarter’s priorities. Yes or no. Each has a date to come back.

Counts

Done already: 7
Out of date: 15
Yes or no, under 2 min: 13
Needs input first: 8
Waiting, no change needed: 8

Every proposed change carries its evidence. “Mark the send done” cites the sent email “Thanks for today”, 25 Sep.

// You stay in charge

You choose how much each job does without asking you.

It acts alone.

Small, provable steps. Example: an item closes when a sent email proves it is done.

It acts, then tells you.

The next decision list says what it did. You can reverse it with one reply.

It prepares. You approve.

Anything sent, paid, published, priced or legal. It prepares the exact action. You send it, change it or bin it. At Sidekick, that is Chase.

How the list gets shorter: one real example

Sun 27 Sep · the list asks
[A prospect] said not now. Close it as dormant?
Chase’s answer, same afternoon
Don’t close it. Follow up in late November if we haven’t heard.
Same day · new rule
When a prospect says “not now”, keep the lead open and set a follow-up about 60 days out.

Next time, Chase is not asked. When the date comes, the note is drafted and he decides whether it goes.

Apart from the AI Opportunity Map report a visitor asks for, no email to a client or prospect goes out without Chase approving it.

Anything AI sends, posts or publishes is logged with who approved it. Nothing that identifies a client appears here without their permission.

Book a free 30-minute call

The first call is free.

// From client work

The same pattern, inside other businesses.

Each one starts on a trigger, does the job end to end and stops for a person. Two are shown without names. Two clients chose to be named.

A local home builder

Proposal engine

A proposal is needed
A review-ready draft from past proposals and pricing rules.
They decide: Scope, price and sign-off

Now drafts proposals with Claude: about 40 hours down to about 4 (client-reported).

An HR consulting firm

Proposal and RFP workflow, brand kit

A request for proposal lands
A draft in the firm's current wording, checked on five points, such as every requirement answered and no old client detail left. Missing facts are clearly marked.
They decide: What gets submitted

Proposal workflow, brand kit and templates delivered and in use. Time saved not measured yet.

Nathan Parkhouse Advisory · The founder’s call preparation

Preparing properly for a call: about 45 minutes down to about 5, by his own estimate.

Chase set up Claude to build a brief before each call from Nathan’s files, calendar and recent emails.

Nathan ParkhouseFounder, Nathan Parkhouse Advisory

How the work flows: Files, calendar and email · Pre-call brief · Nathan reads

Bloom Benefits · Coaching an advisor to build his own AI tools

Chase coached Kevin until he could build his own tools. He then built a branded dashboard for his commissions.

“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.”

Kevin ChaputInsurance advisor, Bloom Benefits

How the work flows: Coaching with Chase · Kevin builds his own tools · Branded commission dashboard

Figures are each client's own estimate.

What still needs work.

It still brings Chase more decisions than he would like. Each new rule makes the list shorter.

// Your business

Want your business to run like this?

In 30 minutes we look at your week and find what is worth building first.

Book a free 30-minute call Free AI Opportunity Map, about 10 minutes

Have a question first? Ask it here, text Chase at 778-999-0985, email, or connect on LinkedIn.