Role Overview
As our GTM Architect, Expansion & Retention, you’ll design, build and ship AI agents and agentic workflows that turn customer signals into saved renewals and cross-sell pipeline.
What You Will Do
You’ll protect renewals by building AI agents that continuously monitor renewal health, grow revenue from existing customers by designing and running an agentic cross-sell motion, and own the data flow between product usage systems and CRM.
Why It Might Be a Fit
You’ll be a good fit if you have a background in RevOps, GTM/marketing operations, customer success operations or GTM engineering, with hands-on experience building automation and a track record of shipping AI agents or LLM workflows to real users.
Requirements
- Background in RevOps, GTM/marketing operations, customer success operations or GTM engineering
- Hands-on experience building automation
- Low-code orchestration (n8n, Make, Zapier or similar)
- 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)
- Working SQL to query and validate usage, support and renewal data
- RevOps systems depth: strong CRM fluency and data modeling (HubSpot experience is a plus)
- Understanding of subscription business metrics (renewal rate, net retention, customer lifetime value)
- Experience with or strong interest in outbound and signal-based go-to-market motions
Benefits
- Base salary: $110,000 – $140,000
- OTE: $120,000 – $155,000
- LTIP program, share in Workleap’s long-term growth
- RRSP + Family health insurance + telemedicine + annual wellness budget
- Flexible vacation policy
- Remote work, with access to our Montreal office
- In-person gathering twice a year
- Claude access, for everyone
To apply for this job please visit job-boards.greenhouse.io.

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