Calgary · AI strategy + implementation

AI that pays for itself.

We find where your business loses the most time, build the AI fix, and prove the result. Fixed fees, local team.

Book a conversation See the packages

The Problem

Your business is already paying for AI.

Not in licence fees, in the hours your people spend on work AI can now do in minutes. Every week you don't fix this, that bill gets bigger.

Where AI Pays Off

What AI gives your business back.

Invoicing & billing

Generate invoices, follow up on late payments, reconcile against time tracking, all without a human in the loop.

Drafting

Quotes, proposals, follow-up emails, and project updates — written in your voice from a few bullet points or a voice note. You review and send. You never start from blank.

Client intake

Every inquiry — website form, email, or phone call — captured and organised automatically. No dropped leads, no manual typing at the end of a long day.

Document review

First-pass review of any contract, supplier agreement, or lease. Flags what needs attention and summarises the rest. Read in minutes, not hours.

Policies & process docs

Capture the workflows that live only in your senior people's heads and turn them into something the rest of the team can run.

Internal knowledge

Search across years of documents, emails, and shared drives like they're one searchable brain.

Marketing & content

Blog posts, social captions, email campaigns — drafted from a brief and ready to edit. You set the direction; AI handles the blank page and the schedule.

Client relationships

Client interactions logged, follow-ups drafted, and next steps surfaced automatically. No relationship falls through the cracks because you were too busy to update a spreadsheet.

Recruiting

Every application screened against your criteria before a human spends a minute on it. Your team reads the shortlist, not the pile.

What We Build

Four ways in. No retainers without proof first.

01 / 04

AI Quick-Check

$500 fixed

2 days

A fast, low-commitment read on where AI can help. The easiest way to get a clear answer without a budget meeting first.

  • 90-minute discovery session
  • Top-5 use cases, ranked
  • Short written report
  • 30-minute readout
Most popular
02 / 04

AI Readiness Audit

$3,000 fixed

1 week

The full diagnostic. A half-day on-site workshop, process maps of your top workflows, and a 90-day deployment plan with tool picks and projected efficiency gains.

  • Half-day on-site workshop
  • Workflow process maps (top 3)
  • Ranked AI use-case shortlist
  • Tool & tier recommendations across the leading AI platforms
  • 90-day deployment roadmap
  • Initial governance policy draft
  • Polished PDF report + 60-minute readout
  • Audit-fee refund if we don't identify clear efficiency gains
03 / 04

Implementation

From $6,000 fixed

2 – 6 weeks per package

Pick the build that fits the workflow you want fixed. Each package is a single fixed price and targets one measurable outcome, with a baseline KPI and an after-number.

  • Workspace Deployment $6,000
  • Custom Integration $10,000
  • Skill or Plugin Build $15,000
  • Baseline KPI capture
  • Build, train, and measure
  • Documentation and runbook
  • Post-launch monitoring (30 days)
04 / 04

Fractional AI Architect

$3,500 / month

6-month minimum, then month-to-month

For businesses past their first build who want a permanent in-house-level capability without the full-time hire. One monthly number; we adjust scope, not price.

  • Monthly strategy session
  • Up to 10 hours of build and maintenance work
  • Quarterly AI-landscape review
  • Staff office hours
  • Slack response within 24 business hours
  • Quarterly KPI and ROI report

Every engagement is a single fixed price, quoted before we start. No hourly billing, no surprise overages. If scope changes, we agree a new number first.

Not sure which tier fits? Start with a conversation.

What We Don't Do

Where we say no.

  • Generic AI training courses

    We're not a training company. Training happens as part of a deployment, not as a product.

  • Replace your best people

    We make your team faster. We don't pretend a model can carry the expertise, judgment, or relationships your best people bring.

  • Sell you vendor licenses or take referral fees

    Our recommendations are independent. If Claude Teams is the right fit we'll say so; if Microsoft Copilot fits better, same.

  • 12-month transformation programmes

    We ship in weeks. If a vendor pitches you a year-long roadmap, get a second opinion (from us if you like).

  • Subcontract anything we sold you

    Two founders, every engagement, end to end. We're not a 1-800 number to a delivery team in another city.

  • Lock you in

    Take the integrations, runbooks, and documentation we ship and run them yourself, with your IT team, or with another vendor. The work is yours.

Founders

Two founders. Every engagement, end to end.

Portrait of Griffin Cheesman

Griffin Cheesman

Co-founder · Strategy & Engagement

Leads strategy, audit delivery, and client engagement at Trailhead. Background in business strategy and operations, with hands-on experience deploying AI workflows inside small business environments.

LinkedIn ↗
Portrait of Ben Adema

Ben Adema

Co-founder · Accounting & Communications

Leads accounting workflows and client communications at Trailhead. Background in accounting and financial reporting, with hands-on experience putting AI to work inside small business environments.

LinkedIn ↗

The start of the journey

Find out if AI can pay for itself at your business.

Free 30 minutes at your office. We come with three use cases costed for your business. If it's not a fit, no follow-up.

Book a conversation