// Inside Sidekick · Updated 1 Oct 2026

A business that moves when something happens, and stops where you decide.

This is how Sidekick runs on AI. Real outputs, names hidden.

Nothing here runs all day in the background. Each system waits for something to happen, does the whole job, then stops at the decision. Chase makes that call. Less comes back to a pile.

Book a 30-minute fit call →See the real outputs

// One real flow · end-to-end testRuns on its own

TriggerA visitor finishes the free AI assessment
ScoresTheir answers, against where AI fits their kind of work
BuildsA report: where to start, what it costs today, what is set up once, what then runs, what you decide
SendsThe report to the visitor and a notice to Chase
StopsWaiting on Chase: the call. Nobody pays until both sides agree it fits

Within 4 secondsBoth emails arrived in the end-to-end test. A sample report is below.

27 Sep 2026: 51 → 13open items checked, cut to yes or no calls
As of 1 Oct: 31written workflows the system runs
Since we started: 15+businesses and teams have worked with Sidekick.
The rule: No email to a client or prospect goes out without Chase approving it.

// 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. A decision Chase makes once becomes a rule, so next time it does not come back to him.

Sales
A first call is booked
A brief from the email thread, the invite, the introducer's notes and public work: what to ask, what not to pitch, and how sure it is.
Chase decides what to say.
Sales
A 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.
Delivery
A fit call goes well
A branded proposal, read by simulated buyers (a sponsor, a skeptic, the day-to-day owner, IT), fixed, then every claim checked against its source.
Chase approves the exact file and sends it.
Delivery
A contract, tax or privacy question comes up
The question framed plainly and a short draft note to the lawyer.
Chase and his lawyer decide.
Operations
Monday comes
Three lines against this quarter's priorities, with the math shown and anything it could not read named.
Chase makes one change for the week.
Website
A visitor finishes the free assessment
A scored report on screen, a link to it emailed to the visitor and a notice to Chase.
Chase holds the call. Nobody pays until both sides agree it fits.

// At your size

What the same pattern looks like in your company.

Illustrative examples. Every rollout starts with the leader, then the leadership team, then the company.

15 people

A professional services firm

A client call ends: recap, follow-up and CRM note ready to review.
A proposal request lands: a checked draft from your past proposals.
Sunday: everything waiting on you, cut to yes or no.

RolloutYou first, then the two or three people who run the work.

120 people

An accounting or advisory firm

A new engagement is agreed: the letter drafted from your templates.
A year-end deadline nears: client chasers drafted for each manager.
Review notes come back: what is still open, file by file.

RolloutPartners first, then managers, then the wider team.

200 people

A construction or property services firm

A daily site report is filed: a summary with issues flagged.
A request for proposal lands: requirements listed, response drafted.
An inspection fails: a fix note with who owns it.

RolloutThe leadership team first, then site supervisors.

// The outputs

Four pieces, as they came out.

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

What started it: Sunday’s weekend reset.
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.

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, still correct: 8

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

// A week, before and after

The same week, with less chasing.

WhenWithout itNow

SundayDig through the inbox, calendar and notes to find what needs you.51 open items checked and cut to 13 yes or no calls. About ten minutes.

Before a first callReread old threads and notes in the minutes before the call.A brief is ready: what to ask, what not to pitch, and how sure it is.

A call endsThe CRM note waits until someone remembers it.The update is drafted from the meeting record and email, ready to check.

MondayGuess where the week stands.Three lines against this quarter's priorities, with the math shown and the gaps named.

A visitor finishes the assessmentA form lands in the inbox and waits.The visitor gets a scored report and Chase gets a notice. Both arrived within 4 seconds in testing.

Only the Sunday list and the assessment emails were timed. The other rows describe what changed, not hours saved.

// You stay in charge

Three levels. You set which job sits where.

It does it.

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

It does it and tells you.

One line on the next list names what it did. One word undoes it.

It prepares. You approve.

Anything sent, paid, published, priced or legal. It prepares the exact action. Chase sends it, changes it or bins it.

How the list gets shorter

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.

No email to a client or prospect goes out without Chase approving it.

The one automatic email is the report a visitor asks for. Every outside action an AI takes is logged with who approved it. Nothing that identifies a client appears here without their permission.

// 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. Three clients chose to be named.

A local home builder

Proposal engine

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

Proposals from about 40 hours to about 4 (client-reported).

An HR consulting firm

Proposal and RFP workflow, brand kit

A request for proposal landsA draft in the firm's current wording, checked on five points. Missing facts are marked, not guessed.They keep: What gets submitted

Brand kit and templates delivered. 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.

“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.”

Nathan ParkhouseFounder, Nathan Parkhouse Advisory

Files, calendar and emailPre-call briefNathan reads

Bloom Benefits · An advisor’s client follow-up

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.”

Kevin ChaputInsurance advisor, Bloom Benefits

Calls and trainingUpdates and draftsKevin reviews

G2 Virtual · The owner’s client work, prepared in parallel

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.”

Jennifer PrincipalliOwner, G2 Virtual

Client files and schedulesWork prepped in parallelJen takes it from there

Figures are each client's own estimate.

What still needs work.

Only one system runs on a clock: the weekday LinkedIn comment drafts. Jobs that used to run on a schedule are paused.
It still brings Chase more decisions than he would like. Each new rule makes the list shorter.
The site chat has raised one hand so far, and an email filter hid that notice for 9 days.

Accepting new engagements

// Your business

Want your business to run like this?

In 30 minutes we look at your week and find the triggers worth building first. You leave knowing what fits, or whether nothing does.

Book a 30-minute fit call →

Or take the free AI assessment, about 10 minutes