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SysAid builds service management software used by 4,000+ organizations in 140 countries and more than 9 million people every day. We're recognized in Gartner's ITSM Magic Quadrant and by AWS as a Rising ISV Star, and generative AI sits at the centre of our product roadmap.
The Role
Our go-to-market stack is already connected to Claude through MCP, and we use it every day for forecasting, pipeline tracking, and account research. What we don't have yet is one person who owns that system end to end. That means two jobs at once. You'll set revenue strategy with the exec team: how a global sales org plans, forecasts, and sells. Then you'll build the workflows that carry it out. Most of that building happens directly in Claude, not as tickets in an ops queue.
What You Will Own:
1. Planning & Forecasting
- The forecast, capacity model, coverage, quota design, segmentation, and territories across regions.
- Tell leadership where growth will come from, where it won't, and what to shift as a result.
2. The Revenue Workflows
- Pipeline generation, enrichment, outreach, deal inspection, forecasting, and reporting.
- Decide what agents run and what people run, build it, keep it running, and replace it when something better ships.
3. Trust & Data Quality
- Evals, guardrails, and data quality, so a forecast an agent produced holds up in a board meeting.
- Know a workflow is drifting before a rep tells you.
4. Revenue Intelligence
- One view of performance from first touch through renewal and expansion.
- Surface risks and opportunities from Gong, Salesforce, and Snowflake before anyone has to ask.
5. The Stack
- Run it as one system. Add what earns its place and cut what doesn't.
What the Work Looks Like
- Late-quarter slippage shows up in one region. By the end of the week, an agent flags every deal without a next step and sends the list to the regional lead.
- Pipeline review prep that used to take a manager two hours is ready before they log on.
- A rep asks for a target list. Instead of building it, you fix the workflow so every rep can pull their own.
- You work through next year's territory design with the revenue leadership team, using a model you built that afternoon.
How We Work
Our footprint is global, and our team is lean, so leverage matters more than headcount. If a task repeats, it becomes a workflow. If a workflow matters, it gets measured. Some things should stay human, like a hard renewal conversation or a judgment call on comp, and we want you to have a clear view on where that line sits. You'll also bring the sales org along: share what you build, write the playbooks, and show people how to work this way themselves.
What You Bring
- You've built things with LLMs that a real team depends on, whether agents, MCP integrations, Claude projects or scripts, and you can walk us through what broke and how you fixed it.
- Strong revenue fundamentals: forecasting, capacity planning, comp, territories, and funnel management. Typically that's 5+ years in RevOps, sales ops, or strategy at a SaaS company, though what you've shipped matters more to us than tenure.
- You're comfortable in Salesforce and SQL (Snowflake or a similar warehouse), and you've used tools like Gong, Clay, Lemlist, or ZoomInfo, or can pick them up quickly.
- You can take a messy dataset and a skeptical executive and leave the room with a decision.
- You're based in Toronto or willing to relocate, and you'll be at Liberty Village four days a week.
How to Apply
Along with your resume, send us something you've built: a workflow, an agent, a repo or a short screen recording. A few lines on what it does and what you'd change next are plenty.
