Your roleWhat you'll be doingWhat We NeedCorpay is currently looking to hire a Chief of Staff within our Product division. This position falls under our Cross Border line of business and is located in Toronto, ON. In this role, you will partner with the Chief Product & Digital Innovation Officer and provide leadership leverage across the Product organization and its work with Technology and other business functions. The role will translate leadership direction into coordinated action, lead complex priorities that span multiple functions, and intervene where important work has stalled or lacks clear ownership. The Chief of Staff will operate above individual delivery workstreams to create an integrated view of outcomes, dependencies, risks, decisions and non-technical requirements. This person will help ensure that strategic initiatives move forward as coherent programs rather than disconnected Product, Engineering or functional activities. You will report directly to the Chief Product & Digital Innovation Officer and regularly collaborate with multiple departments.
Role ResponsibilitiesThe responsibilities of the role will include:
Executive partnership and priority advancement- Partner closely with the CPO to identify the highest-impact priorities and translate them into clear plans, owners, decision points and measurable outcomes.
- Prepare strategy materials, Board and leadership documents, briefings and communications that distil complex information into clear choices and recommendations.
- Maintain an executive view of the CPO's highest-priority commitments, risks and decisions, drawing on established Product and organizational reporting and ensuring appropriate follow-through and escalation
- Represent the CPO's intent and context in meetings and working sessions, while using sound judgement on when decisions must return to the CPO.
- Improve the effectiveness of the CPO's time by ensuring attention is focused on the decisions, relationships and interventions that most require executive leadership.
- Act as a trusted thought partner to the CPO, constructively challenging priorities, assumptions and allocation of leadership attention where appropriate.
Cross-functional program leadership- Lead selected strategic initiatives that cut across Product, Engineering, Legal, Compliance, Operations, Commercial and other functions.
- Identify missing workstreams and ensure supporting requirements such as legal, contractual, operational, customer, control, documentation, testing and change impacts are addressed.
- Establish fit-for-purpose initiative-level governance, operating cadences, status reporting and decision forums for the strategic initiatives they lead, leveraging established Product operating mechanisms wherever appropriate.
- Coordinate stakeholders and sequencing, resolve blockers, and ensure decisions are prepared and progressed at the right level.
- Mobilize initiatives quickly, stabilize delivery and transition enduring responsibilities to an appropriate permanent owner once the work is established.
Organizational problem-solving- Step into high-priority issues where work is stalled, ownership is unclear, processes are broken or an urgent gap requires senior intervention.
- Diagnose the underlying problem, clarify accountabilities and establish a practical route to resolution.
- Bring structure to unorganized or incomplete information, converting leadership discussion into coordinated execution.
- Anticipate emerging risks and address them before they become material obstacles.
- Build alignment across teams and leaders, using influence, judgement and credibility rather than reliance on direct authority.
Qualifications & Skills- Significant experience in a senior Product, Technology, strategy, business operations, transformation or program leadership role within a complex organization.
- Demonstrated understanding of Product and Engineering operating environments, including how strategy, roadmaps, delivery, platform dependencies and non-technical requirements connect.
- Proven ability to lead complex, cross-functional initiatives and drive outcomes across senior stakeholders without direct authority.
- Strong strategic thinking, analytical problem-solving and program management capabilities, with the ability to move between the enterprise view and delivery detail.
- Strong business and organizational judgement, with the ability to understand executive intent, make appropriate decisions independently and recognize when an issue requires escalation.
- Exceptional written and verbal communication skills, including experience preparing executive, leadership or Board-level materials.
- Highly organized and execution-focused, with the judgement to prioritize, simplify and create structure in ambiguous situations.
- Experience in payments, financial services, regulated technology, platform integration or global product organizations is preferred.
- Bachelor's degree or equivalent practical experience; advanced degree or relevant professional qualification is an asset.
Benefits & Perks- Comprehensive Benefits Package including, Medical, Dental, Vision and Paramedical benefits, as of day one
- Optional company match RRSP program
- Virtual fitness classes offered company-wide
- Time-off including major holidays, vacation, sick, personal, & volunteer time
- Discounted gym membership rate
- Philanthropic support with both local and national organizations
- Fun culture with company-wide contests and prizes
Pay TransparencyThe expected salary range for this position is $170,000-200,000 CAD, based on the candidate's work location. This range reflects a good faith estimate of the expected compensation for this role at the time of posting. The final offer will be determined based on job-related factors including skills, experience, qualifications, and applicable market conditions. Compensation may vary based on geographic location and will be confirmed during the hiring process. Additional compensation and benefits, including incentive programs, health coverage, retirement plans, paid time off, and other benefits (where applicable), may also be provided.
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