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 thats whats 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 seats 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 doesnt 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 whats 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 thats the fastest path to unblocking something.

Requirements

• 812 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 thats 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:

• $140000 - 160000 CAD

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