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Upshop
Mississauga
Source: Upshop careers · View original posting
From Upshop's posting. “We” and “our” refer to the employer.
Director, Business Operations
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.
Full visibility into current PDLC, OKR/Rocks, and dashboard state across all suites; a documented point of view on what's working and what needs to change.
Clear delineation established between what this role owns strategically and what the Program Manager owns operationally.
At least one concrete tooling or process improvement shipped hands-on (not just proposed).
A roadmap for methodology/traceability maturity presented to leadership.
Measures of Success / KPIs
OKR/Rocks traceability is complete and current across all suites — leadership can trace goal to execution without manual reconciliation.
KPI/exec dashboards are trusted as the single source of truth for delivery health, not rebuilt in spreadsheets before leadership meetings.
PDLC and methodology standards are documented, versioned, and consistently followed across suites — not just referenced.
Org structure documentation stays current within days of any change, rather than drifting until someone flags it as stale.
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.
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