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 ShareGate, 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

ShareGate’s customers generate rich signals (product usage, support interactions, renewal dates), but those signals aren’t yet connected into an engine that protects and grows the revenue we already have. As our GTM Architect, Expansion & Retention, you’ll design, build and ship AI agents and agentic workflows that turn those signals into saved renewals and cross-sell pipeline. This is an embedded engineering role within GTM, not back-office ops: you’ll apply the signal-based, agent-first approach we already use for new customer acquisition to the customers we already have.

Your impact:

Protect renewals by building AI agents that continuously monitor renewal health and flag at-risk accounts to Account Managers early, with context, recommended next steps and enough lead time to act.
Grow revenue from our existing customers by designing and running an agentic cross-sell motion: score fit for our second product line, research each account, personalize outreach, qualify interest and route genuine intent to the right salesperson with the full context needed to close.
Define the signals your agents need and partner with Revenue Systems, which builds and owns the data flow between product usage and the CRM. Validate the data with SQL before you act on it.
Replace manual workflows with AI agents and reusable pipeline modules (not one-off automations) that Account Management and Sales can run and own on their own.
Tune both motions by owning reporting on pipeline generated, conversion, renewal outcomes and revenue impact, and by running controlled experiments without adding headcount.
Drive adoption by turning everything you build into SOPs, demos and playbooks, so the team uses what you ship, not just appreciates it.

Your team

You’ll join a GTM engineering effort that already runs a signal-based, agent-first approach to new customer acquisition, and now points it at the customers we already have. The challenge: connect usage, support and renewal signals into agents that reduce the friction between signal and action. The tools, plays and channels will evolve; that mission won’t.

Our stack: low-code orchestration (n8n, Make, Zapier or similar), Python or TypeScript, SQL on our data warehouse, and our CRM (HubSpot).

What you'll bring

Background in RevOps, GTM/marketing operations, customer success operations or GTM engineering, with hands-on experience building automation;
Hands-on experience with low-code orchestration (n8n, Make, Zapier or similar), plus working knowledge of Python or TypeScript for API integrations and data transformation;
fluency with agentic tools and MCP connectors. Strong LLM workflow design (agent orchestration, tool use, evaluation), sound judgment on when AI adds leverage versus complexity, and a track record of shipping AI agents or LLM workflows to real users, not just prototypes;
Working SQL to query and validate usage, support and renewal data., so you can build and trust the data behind your agents;
CRM fluency (HubSpot a plus): enough to des

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