Senior AI Developer - Product Operations

Location: Montreal

Company Description  Workleap is a Montreal-based tech company, founded in 2006. We're builders at heart, we make simple products that actually matter to the people who use them. We have two product lines:
Workleap Agent, our newest solution built to make every manager more effective, and Share Gate, the world's leading solution for Microsoft 365 migration and governance. More than 15,000 companies worldwide trust us to do exactly that. We're intentional about who joins us. If you're the kind of person who gets excited by a hard problem and wants to help shape what comes next, there's a place for you here.

Your role
At Workleap, our engineering teams already ships more than twice as fast with AI. Now we’re expanding beyond code to everything around it: briefs, specs, design, launch, and measurement. The idea is simple: agents do the work, and people make the calls. We’ve are rethinking how we build products and are exploring the technical possibilities, this is just the beginning. As a Senior AI Developer, you’ll join us to shape and build this solution ensuring that we have solid technical foundation.
Your impact:
Ship the first production agents with our Product Managers, starting with brief creation and the Product Manager-to-design handoff, then extend to the rest of the product lifecycle.
Shape the shared architecture and standards (orchestration, skills, memory, evals, guardrails) so that both our product lines are built on the same foundation.
Own the production quality of these agents: observability, testing, security, and cost built in from the start, with human approval at every gate.
Co-design with Product Managers: understand how they work, reuse what they’ve already automated, and ship small iterations they test and adopt.
Measure what works: time saved, time from customer signal to shipped decision, and cost per agent and per feature, then cut what doesn’t add value.
Grow others: share your agent development practices so the team can build, run, and improve agents on their own.

Your team  Over the next 6 to 12 months, you’ll work on questions like: how does an agent turn an idea into a brief that a Product Manager approves without rewriting it? How do specialized agents pass context without losing it or blowing up costs? How do we decide an agent is reliable enough to lighten a gate? The vision is set, and a proof of concept in Slack is underway: you’re joining early enough to shape the architecture and turn this start into a production standard.
You’ll join the  Product Ops team , a small team serving Product Manager across two product lines that already owns tracking, product data quality, and analytics. You’ll work daily with this team, our AI-Software Development Life Cycle team, which already automates software delivery, and with our Product Managers working on both product lines. You’ll also partner with the Senior AI Developer on our Data team to share patterns and tooling.

We use AI every day, decide fast, and ship in iterations.
What you'll bring   Strong production engineering across the agent development lifecycle;
Hands-on experience designing and shipping multi-agent systems to production: orchestration, tools, context, and memory, integrated with tools like Slack, Atlassian, and MCP;
Experience instrumenting and evaluating non-deterministic systems: evals, observability, regression testing, and cost tracking;
Sound architectural judgment across reliability, security, and cost, including which model fits which job, and the confidence to form and defend a technical opinion;
Experience building components or tooling that other people adopt;
Real product sense: you understand how a Product Manager works and you build with users, not for them;
A taste for building as a team…