Director, Business Operations

Director, Business Operations
Location: Mississauga, Ontario
Role Summary
Upshop is hiring a senior operator to own the strategic half of how our Product & Engineering organization runs — the methodology, the traceability, and the executive visibility layer that sits above day-to-day program cadence. This role picks up and expands the operating model currently run by the VP, Business Operations, while day-to-day PDLC cadence continues to be owned at the program-manager level, which reports into this role. As the operating model matures, the role takes on more of the operational ownership that sits with the VP, Business Operations today — vendor & contract management, and budget and headcount planning input — becoming the primary owner of how the Product & Engineering org plans, tracks, and reports, not just the operator of it.
This is a player-coach role. We need someone who can set direction and manage a direct report, but who is also still hands-on — someone who will personally get into Jira, PagerDuty, Zendesk-Exalate, Asana, and our reporting/dashboard stack to fix, build, or rework a process or tool when that's what's needed to move the needle, not just spec it for someone else to build. That includes using AI as a default part of how the work gets done — automating dashboard builds, synthesizing delivery data, and speeding up documentation — not treating it as a side experiment.
Note on scope: this seat's seniority comes from what it owns — strategic operating-model ownership across the entire Product & Engineering org — not from team size. It currently has one direct report, with room to grow as the function matures.
Key Responsibilities
Own PDLC methodology and maturity across the Product & Engineering org — the framework everyone plans, tracks, and reports against.
Own the design of Product & Engineering planning cadences — PI/quarterly planning structure, ceremonies, and calendar — with the Product Operations Lead executing against it.
Own resource and capacity planning across the org — headcount allocation, suite coverage, and hiring/backfill sequencing — partnering with the VP, Business Operations for final sign-off.
Drive cross-department scaling of the operating model, extending what works in one suite or team to the rest of the org.
Own OKR/Rocks traceability strategy — how goals connect to execution, and how that gets measured and reported.
Own KPI and executive dashboard strategy — the metrics and standards leadership relies on to judge delivery health across the org.
Own org structure and role documentation as the definitive record of how Product & Engineering is organized, keeping it current as the org evolves.
Own the tooling strategy and architecture behind how Product & Engineering operates — Atlassian/Jira, PagerDuty, Zendesk-Exalate, Asana — including the integrations and process solutions the org needs as it scales, executed directly or through the Product Operations Lead.
Identify and implement AI-assisted automation across reporting, dashboards, and process documentation — reducing manual overhead as the org scales rather than adding headcount to absorb it.
Partner with the CPO, VP of Engineering, and Directors of Engineering to keep the operating model aligned with how