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 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 CAD

The successful candidate’s starting salary will be determined based on permissible, non-discriminatory factors such as skills, experience, and geographic location.