Staff engineer architecting event - sourced, offline - first ordering systems for Owner’s all - in - one restaurant platform. Improving replication, reconciliation, observability, and recovery across distributed point - of - sale devices.
About the role
- GTM engineer building AI agents that protect renewals and generate cross-sell pipeline. ShareGate provides Microsoft 365 migration and governance software for IT teams.
Responsibilities
- Design, build and ship AI agents and agentic workflows that turn customer signals into saved renewals and cross-sell pipeline
- Monitor renewal health and flag at-risk accounts to Account Managers with context, recommended next steps and sufficient lead time
- Design and run an agentic cross-sell motion, including fit scoring, account research, personalized outreach, interest qualification and routing intent to salespeople
- Own data flows between product usage systems and the CRM, including data quality, sender reputation and attribution accuracy
- Replace manual workflows with reusable AI-agent pipeline modules that Account Management and Sales can operate independently
- Own reporting on pipeline generated, conversion, renewal outcomes and revenue impact
- Run controlled experiments without adding headcount
- Create SOPs, demos and playbooks to drive adoption
Requirements
- 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)
- Working knowledge of Python or TypeScript for API integrations and data transformation
- Fluency with agentic tools and MCP connectors
- Strong LLM workflow design, including agent orchestration, tool use and evaluation
- Track record of shipping AI agents or LLM workflows to real users
- Working SQL to query and validate usage, support and renewal data
- Strong CRM fluency and data modeling; HubSpot experience is a plus
- Experience with clean integrations between product usage data and CRM
- Deliverability management for outbound
- Understanding of subscription business metrics, including renewal rate, net retention and customer lifetime value
- Experience with or strong interest in outbound and signal-based go-to-market motions
- Ability to work directly with Sales and Account Management and translate complex builds into plain language
- Ability to earn adoption through demos and handoff documentation
- Bonus: experience building AI-driven qualification or scoring systems
- Bonus: B2B SaaS background with multiple product lines, ideally product-led or demo-led
- Bonus: published technical content making complex systems accessible
Benefits
- 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
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