Director, Business Operations

Director, Business Operations
Location:
Mississauga, OntarioRole 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 Product and Engineering actually work.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.What Success Looks Like in the First 90 Days
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.Requirements
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.Comfortable getting hands‑on with tooling — dashboards, workflow automation, integrations (Jira, Asana, PagerDuty, or comparable) — beyond just requirements‑gathering for someone else to build.Experience managing process documentation, internal knowledge bases, and change communication well enough that new standards actually stick, not just get published.Strong written and verbal communication;
comfortable presenting to executive leadership (CPO, VPs).Experience with OKR/goal‑traceability frameworks ("Rocks" or equivalent).Nice to Have
Prior chief‑of‑staff or business‑operations experience reporting directly into a VP/C‑level.Experience in a multi‑suite or multi‑product organization with distributed engineering/product leadership.Background in defining or scaling program‑management functions (i.E., has hired/managed PMs before).Experience evaluating or integrating AI/automation into operational workflows to reduce manual effort and scale process without adding headcount.Familiarity with change‑management methodologies for rolling out new ways of working across multiple teams.The estimated pay ranges for this role are as follows:$140,000 - 160,000 CADThe successful candidate’s starting salary will be determined based on permissible, non‑discriminatory factors such as skills, experience, and geographic location.
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