A digital health company

A Canadian digital health company building an employee-benefits platform for employers and their benefits partners. Most of the team was already using AI every day. They brought us into their team offsite to turn individual habits into a shared way of working.

The challenge: Individual AI use, member data in the way of automation

The team knew it was scratching the surface. Most of them used Claude daily, but the use was shallow and individual: no connectors into the tools that hold their work, no shared context, and no way of passing on what one person had figured out. Every person named the same rule in their pre-work: AI can draft, but a human stays in the loop on anything that ships.

Member data was the wall. Sensitive health information sat inside their member systems, and with no clear line on what could touch a model, it blocked everything: no CRM automation, no connected tools, nothing past chat. We were brought in to draw that line, and we started by getting the whole team onto one shared workspace on a single team plan.

The solution: A survey, a half-day workshop, one-on-ones, a roadmap

We sent out a survey ahead of the offsite that mapped each role's time sinks, then ran a half-day AI training workshop at the offsite itself: a short security and data primer, then hands-on rounds on connectors, scheduled tasks, skills, and dispatch, each taught, demoed on the team's own work, and tried live in the room.

Afterwards, one-on-one meetings with each employee: what they had tried, where they were stuck, and the first automation worth building for their role. That fed a role-by-role roadmap with three scored automations per person, sequenced over the following two months.

The outcomes: Two CRM instances, sales automation within a week

The member-data question got a hard answer. Their CRM was split into two instances: one holding member data, closed to AI entirely, and one cleared for sales automation. With that line drawn, the team connected the tools that hold their work and started building.

The designer turned four one-pagers into a French copy deck in one sitting, work that would have gone out to a translator, and set up recurring monitoring for competitors and policy changes. The engineers went deeper into code-level workflows. Sales outreach automation was underway within a week of the one-on-ones, and the roadmap gives each person their next build.