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.