Director, Business Operations 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.

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.

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.

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.

Partner with the 3 suite Program Managers for the delivery data that feeds OKR/Rocks traceability and the KPI/exec dashboards — this role depends on their input but doesn't manage them directly.

At least one concrete tooling or process improvement shipped hands‑on (not just proposed).

Vendor & contract management and budget/headcount planning input transfer cleanly from the VP, Business Operations to this seat, on a defined cadence, without loss of accuracy.

The Product Operations Lead runs the tactical cadence independently — this role sets direction and standards, and only steps in hands‑on when that's the fastest path to unblocking something.

8–12+ years in business operations, chief of staff, technical program management, or product operations roles at a fast‑growing company — SaaS strongly preferred, but comparable scaling experience in adjacent industries will be considered.

Demonstrated success building or maturing an operating model or PDLC framework — not just operating within one that's already mature.

Proven people‑management experience, with a track record of developing and scaling operations or program‑management talent, not just staying hands‑on personally.

Experience managing process documentation, internal knowledge bases, and change communication well enough that recent standards actually stick, not just get published.

Prior chief‑of‑staff or business‑operations experience reporting directly into a VP/C‑level.

Background in defining or scaling program‑management functions (i.e., has hired/managed PMs before).

Familiarity with change‑management methodologies for rolling out new ways of working across multiple teams.

140,000 - 160,000 CAD

📌 Online Business Head of Operations (Mississauga)
🏢 Upshop
📍 Mississauga