Head of Product Operations

Corpay • Toronto, ON

3d • Hybrid

About The Position

CORPAY is currently looking to hire a Head of Product Operation within our Product Operations division. This position falls under our Corpay Cross Border’s line of business and is located in Toronto, ON. In this role, you will establish and lead the Product Operations function from the ground up, reporting directly to the Chief Product Officer. You will start with the most urgent need — portfolio visibility and planning cadence — and expand into PM tooling, ways of working, and broader operational infrastructure over the following 12 months. Critically, this role owns the coordination and communication bridge between the product function and engineering, which operates as a separate organisational function. You will inherit one direct report: a Product Operations Specialist with Jira and organisational expertise who is already working to align tooling usage across the function.
The right candidate is someone who sees portfolio management and product operations as two sides of the same coin: the portfolio view tells you what is happening across the function; the operating infrastructure is what makes that view sustainable and accurate at scale. And critically, someone who understands that a product function only delivers when it moves in genuine lockstep with engineering.

Requirements

• Operated at the intersection of portfolio management and product operations
• 8–15+ years across Product Operations, Programme Management, Product Leadership, or a combination
• Demonstrable experience building or significantly improving portfolio management functions — not just operating within established ones
• Proven experience coordinating planning and communication between product and engineering as separate organisational functions — comfortable operating as a neutral bridge between two leadership teams
• Familiarity with PM tooling governance — Jira at a portfolio/programme level, and ideally roadmapping tools such as Productboard, Aha!, or similar
• Experience defining and embedding ways of working across PM teams — process design that feels like support, not overhead
• Background in fintech, payments, FX, banking, or another regulated financial services environment
• Experience working across multiple simultaneous product lines with cross-functional interdependencies
• People management experience — comfortable developing a direct report and building a small function over time

Responsibilities

• Establish and maintain a single, trusted portfolio view across all product lines
• Define and standardise how initiatives are captured, categorised, status-reported, and escalated
• Own the quarterly planning cycle in partnership with product area leaders and the Chief Product Officer
• Surface prioritisation trade-offs and investment conflicts early, with data to support decisions
• Integrate regulatory and compliance milestones into portfolio tracking as a first-class concern
• Own the planning and communication interface between the product function and engineering leadership — ensuring both functions are operating from a shared view of priorities, capacity, and delivery commitments
• Establish regular cross-functional planning cadences between product and engineering, creating structured forums where roadmap commitments are tested against engineering capacity before they are made
• Maintain visibility of engineering capacity constraints and surface these proactively into portfolio prioritisation decisions — reducing the gap between what product plans and what engineering can deliver
• Build a shared language and operating rhythm between product and engineering so that dependencies, delays, and trade-offs are surfaced early and resolved at the right level
• Act as a trusted neutral party between the two functions — not an advocate for either side, but a facilitator of better joint decisions
• Map and actively manage cross-team dependencies spanning engineering, risk, compliance, and GTM
• Flag risks and blockers proactively — reduce the number of escalations that arrive at leadership without warning
• Run recurring portfolio reviews and operating cadences that give area leaders visibility and leadership confidence
• Work with your direct report to evolve the existing Jira infrastructure to support portfolio-level tracking, not just team-level sprint management
• Define and drive adoption of consistent ways of working across PM teams — how initiatives are written up, tracked, and reported
• Evaluate and implement additional tooling where Jira alone is insufficient (roadmapping, dashboarding, executive reporting)
• Create standards that reduce noise and improve the quality of information flowing into the portfolio view
• Translate portfolio complexity into clear, outcome-focused narratives for the Chief Product Officer and senior leadership
• Build reporting rhythms that give leadership early signals, not retrospective summaries
• Ensure the portfolio view is actively used and trusted — not a compliance exercise
• Manage, coach, and develop the Product Operations Specialist — providing direction, clarity, and growth opportunities
• Build the broader Product Ops function over time, including defining the headcount and capability plan for the next phase
• Act as a trusted partner to product area leaders, engineering leadership, the Chief Product Officer, and senior cross-functional stakeholders

Benefits

• Medical, Dental & Vision benefits available the 1st month after hire
• Automatic enrollment into our 401k plan (subject to eligibility requirements)
• Virtual fitness classes offered company-wide
• Robust PTO offerings including major holidays, vacation, sick, personal, & volunteer time
• Employee discounts with major providers (i.e. wireless, gym, car rental, etc.)
• Philanthropic support with both local and national organizations
• Fun culture with company-wide contests and prizes

What This Job Offers

• Job Type: Full-time
• Career Level: Senior
• Education Level: No Education Listed