About

The story.

Trailhead started because of a gap we kept seeing: between buying AI tools and actually using them. Firms would expense a seat, give it to a curious associate, and call it their "AI initiative." Six months later nothing had changed except the line item on the SaaS bill. The technology was capable. The work to integrate it into how a firm actually operates was just never done.

Calgary is a city of professional services firms (law, accounting, engineering, agencies) that are exactly the right size to benefit from AI and exactly the wrong size to staff an in-house AI team. They need someone who can show up on a Tuesday morning, understand the workflow, and ship the thing by month-end. That's what we do.

We chose to be specialists rather than generalists. Our deepest depth is with Anthropic's Claude, the enterprise AI platform with the strongest security, integration, and reasoning posture for the firms we work with. Every engagement still starts from your workflow, not from a tool we want to sell you. Specialisation lets two people credibly outdo a generalist consultancy on any given workflow. It's the only way a small firm gets the depth of expertise that justifies bringing us in.

The Calgary downtown skyline
Calgary, AB

The founders

Two founders. Complementary skill sets, not duplicated ones.

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 professional services environments.

His day-to-day at Trailhead is mapping where AI fits inside a firm (usually invoicing, drafting, intake, or document review) and making sure each deployment is something a partner can defend in the budget meeting six months later. Spends most engagement time on-site, not behind a deck.

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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 professional services environments.

His day-to-day at Trailhead is the finance and communications side of a deployment (reconciliations, month-end reporting, client correspondence) and making sure the numbers behind every AI workflow hold up. Focused on the practical follow-through that turns a build into something a firm actually keeps using.

LinkedIn ↗

How we work

Four principles. We say them out loud so you can hold us to them.

Specialists, not generalists.
We say no to AI work that isn't a fit for our depth. That keeps the work we do say yes to demonstrably better than a generalist would deliver.
Fixed fees only.
You know the cost before we start. No timesheets, no scope creep, no "well it ended up being more complicated than we thought."
Measured outcomes.
Every sprint has a baseline KPI captured before we start and an after-number captured before we leave. If the math doesn't work, we tell you.
Local and accountable.
We come to your office. We're not a 1-800 number to Toronto, and we're not subcontracting the work to anyone you haven't met.