Location: REMOTE / Toronto, Ontario
This job allows you to work remotely.
Runbook is building the AI workforce for the backbone of the physical economy, replacing the hidden layer of human busywork (emails, spreadsheets, phone calls, legacy software) with AI agents that run messy, multi-day workflows end to end, learn from every correction, and hit 90%+ autonomous execution in production. Runbook's agents currently run real operations for real customers today, from mid-market field services companies to large Fortune 500 enterprises. Founded by Obaid Khan, who previously co-founded Motive and scaled it past $350M in revenue and a $5B+ valuation. Small, high-velocity founding team with roots at Meta, Amazon, Discord, Carta and Scale AI.
This is a generalist role on the post-sales Deployments team: the person is the one who gets Runbook's AI product working inside a real customer's business. They learn how a customer's workflows actually get done, deploy AI agents to handle them, and keep fine-tuning until the agent runs reliably on its own -- turning something that looks good in a demo into something the customer can count on every day. Responsibilities span requirements discovery on messy real-world processes, building trusted-advisor relationships directly with enterprise customers, iterating agents (prompt engineering, skill files, process changes, or looping in engineering) until they hit a high autonomy bar, and owning each deployment end to end from first pilot through production.
This is the first Canada-based hire for this role (Runbook is SF-based and in-office); the person may be part of a larger Canadian team over time. Runbook is hiring both an Agent Product Ops Lead (new grad/early-career) and a Senior Product Ops Lead (experienced) version of this role.
Must Have Skills:
Exceptional customer-facing communication -- able to run a working session with an enterprise stakeholder and debug shoulder-to-shoulder with engineers/PMs. Comfort with ambiguity -- can hold a messy, undocumented real-world process in their head and spot the one wrong assumption that breaks things downstream. AI-tooling fluency and curiosity -- comfortable as a power user of modern AI tools; has built something with AI (does not require a CS degree or professional coding background). High agency and bias for action -- makes the call and fixes what's broken rather than waiting for permission. End-to-end ownership -- owns a deployment from first pilot to production with no handoffs. Relentless, detail-oriented problem-solving -- keeps testing approaches until a workflow holds at a high quality bar.
Nice to Have Skills:
Domain knowledge of operationally-intensive industries (logistics, field services, manufacturing, supply chain). Experience in a high-growth technology startup environment. Analytical academic background (engineering, computer science, economics, business, finance). Comfort with an in-office, high-velocity, minimal-process culture.
