OverviewCORPAY 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.How We WorkAs the Head of Product Operations, you will be expected to work in a hybrid environment. CORPAY will set you up for success by providing:Assigned workspace in the Toronto, ON office, working 3-4 days in the office.Company-issued equipment + remote accessRole ResponsibilitiesThe responsibilities of the role will include:Portfolio Visibility & Planning — Immediate PriorityEstablish and maintain a single, trusted portfolio view across all product linesDefine and standardise how initiatives are captured, categorised, status-reported, and escalatedOwn the quarterly planning cycle in partnership with product area leaders and the Chief Product OfficerSurface prioritisation trade-offs and investment conflicts early, with data to support decisionsIntegrate regulatory and compliance milestones into portfolio tracking as a first-class concernEngineering Coordination & Planning Alignment — Immediate PriorityOwn 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 commitmentsEstablish regular cross-functional planning cadences between product and engineering, creating structured forums where roadmap commitments are tested against engineering capacity before they are madeMaintain visibility of engineering capacity constraints and surface these proactively into portfolio prioritisation decisions — reducing the gap between what product plans and what engineering can deliverBuild 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 levelAct as a trusted neutral party between the two functions — not an advocate for either side,



but a facilitator of better joint decisionsDependency & Risk ManagementMap and actively manage cross-team dependencies spanning engineering, risk, compliance, and GTMFlag risks and blockers proactively — reduce the number of escalations that arrive at leadership without warningRun recurring portfolio reviews and operating cadences that give area leaders visibility and leadership confidencePM Tooling & Ways of Working — Rapid FollowWork with your direct report to evolve the existing Jira infrastructure to support portfolio-level tracking, not just team-level sprint managementDefine and drive adoption of consistent ways of working across PM teams — how initiatives are written up, tracked, and reportedEvaluate 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 viewExecutive Reporting & CommunicationTranslate portfolio complexity into clear, outcome-focused narratives for the Chief Product Officer and senior leadershipBuild reporting rhythms that give leadership early signals, not retrospective summariesEnsure the portfolio view is actively used and trusted — not a compliance exerciseTeam Leadership & Function BuildingManage, coach, and develop the Product Operations Specialist — providing direction, clarity, and growth opportunitiesBuild the broader Product Ops function over time, including defining the headcount and capability plan for the next phaseAct as a trusted partner to product area leaders, engineering leadership, the Chief Product Officer, and senior cross-functional stakeholdersQualifications & SkillsWe are looking for someone who has operated at the intersection of portfolio management and product operations — not purely one or the other. The following experience profile fits:8–15+ years across Product Operations, Programme Management, Product Leadership,



or a combinationDemonstrable experience building or significantly improving portfolio management functions — not just operating within established onesProven experience coordinating planning and communication between product and engineering as separate organisational functions — comfortable operating as a neutral bridge between two leadership teamsFamiliarity with PM tooling governance — Jira at a portfolio/programme level, and ideally roadmapping tools such as Productboard, Aha!, or similarExperience defining and embedding ways of working across PM teams — process design that feels like support, not overheadBackground in fintech, payments, FX, banking, or another regulated financial services environmentExperience working across multiple simultaneous product lines with cross-functional interdependenciesPeople management experience — comfortable developing a direct report and building a small function over timeBenefits & PerksMedical, Dental & Vision benefits available the 1st month after hireAutomatic enrollment into our 401k plan (subject to eligibility requirements)Virtual fitness classes offered company-wideRobust PTO offerings including major holidays, vacation, sick, personal, & volunteer timeEmployee discounts with major providers (i.E. wireless, gym, car rental, etc.)Philanthropic support with both local and national organizationsFun culture with company-wide contests and prizesEqual Opportunity / Pay TransparencyCorpay is an Equal Opportunity Employer. Corpay provides equal employment opportunities to all qualified applicants without regard to race, color, gender (including pregnancy), religion, national origin, ancestry, disability, age, sexual orientation, gender identity or expression, marital status, language, ancestry, genetic information and/or military status or any other group status protected by federal or local law. If you require reasonable accommodation for the application and/or interview process, please notify a representative of the Human Resources Department.This salary range is provided for locations which require such disclosure. Where a position or applicant may fall in a particular wage range depends on a number of factors including but not limited to skill sets, experience training licenses and certifications (if applicable), and other business and organization needs. The disclosed range has not been adjusted for the applicable geographic markets. At Corpay it is not typical for an individual to be hired at or near the top of the range for their role and compensation decisions depend on the facts and circumstances of each case. The estimate of the minimum and maximum salary range is CAD $150,000-$170,000.For more information about our commitment to equal employment opportunity and pay transparency, please click the following links: Canadian Human Rights Act – Grounds of Discrimination, Employment Equity Act (Canada) and BC Pay Transparency.#J-18808-Ljbffr

📌 Head Of Product Operations - C$150,000 - C$170,000 A Year (Winnipeg)
🏢 Corpay
📍 Winnipeg