Director of Strategic Initiatives – Integrated Payments
What We Need
We are seeking a highly motivated and results-driven Director of Strategic Initiatives to lead cross-functional programs and drive high-impact projects that align with our long-term vision. This role serves as a strategic partner to senior leadership, translating high-level objectives into actionable plans and ensuring their successful execution across the Global Integrated Payments group for Corpay Cross-Border. This position will report directly to the Chief of Sales Officer and is located in Toronto.
The ideal candidate is a strategic thinker, skilled operator, and change agent who thrives in a dynamic, fast-paced environment.
How We Work

As a Director of Strategic Initiatives you will be expected to work in our Toronto office. Corpay will set you up for success by providing:

• Assigned workspace in our Toronto Office.
• Company-issued equipment
• Formal, hands-on training

Roles Responsibilities

• Strategic Planning & Execution: Collaborate with executives to define and prioritize key initiatives; develop comprehensive project plans, including timelines, milestones, and KPIs.
• Program Management: Lead cross-functional initiatives from concept to implementation, ensuring alignment with strategic goals and consistent execution across teams.
• Change Management: Drive organizational change by championing new initiatives, aligning stakeholders, and minimizing resistance through communication and engagement.
• Stakeholder Communication: Provide regular updates and insights to senior leadership and key stakeholders through dashboards, reports, and presentations.
• Business Analysis & Insights: Conduct market research, competitive analysis, revenue and forecast modeling to support the Chief Sales Officer and Managing Director with strategic decisions.
• Innovation & Growth: Identify and assess new opportunities for innovation, partnerships, and operational efficiencies.
• Operational Excellence: Develop and improve processes and frameworks that enhance execution, collaboration, and accountability across strategic initiatives.

Qualifications and Skills

• Bachelor’s degree in Business, Economics, or a related field; MBA or equivalent preferred.
• 8+ years of progressive experience in strategy, management consulting, business operations, or a similar role.
• Proven track record of successfully managing complex, cross-functional projects in a high-growth or enterprise environment.
• Exceptional communication, presentation, and interpersonal skills.
• Strong analytical skills and business acumen.
• Ability to influence and work effectively with stakeholders at all levels.
• Experience with project management tools and strategic planning frameworks (e.g., OKRs, Balanced Scorecard, etc.).

Preferred Attributes
Experience in the cross-border payments space.
Entrepreneurial mindset with a bias for action.
Comfortable navigating ambiguity and making data-informed decisions.
High EQ with the ability to lead without authority.

Benefits & Perks

• 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

This salary range is provided for locations which require such disclosure. Where a position or applicant may fall in a particular wage range varies depending on a number of factors, including but not limited to skill sets, experience, training, licensure 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 are dependent on the facts and circumstances of each case. An estimate of the minimum and maximum salary range is $200K – $210K CAD OTE.
Equal Opportunity/Affirmative Action Employer
Corpay is an Equal Opportunity Employer. Corpay provides equal employment opportunities to all employees and 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, veteran 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.
For more information about our commitment to equal employment opportunity and pay transparency, please click the following links: EEO and Pay Transparenc

• Strategic Planning & Execution: Collaborate with executives to define and prioritize key initiatives; develop comprehensive project plans, including timelines, milestones, and KPIs.
• Program Management: Lead cross-functional initiatives from concept to implementation, ensuring alignment with strategic goals and consistent execution across teams.
• Change Management: Drive organizational change by championing new initiatives, aligning stakeholders, and minimizing resistance through communication and engagement.
• Stakeholder Communication: Provide regular updates and insights to senior leadership and key stakeholders through dashboards, reports, and presentations.
• Business Analysis & Insights: Conduct market research, competitive analysis, revenue and forecast modeling to support the Chief Sales Officer and Managing Director with strategic decisions.
• Innovation & Growth: Identify and assess new opportunities for innovation, partnerships, and operational efficiencies.
• Operational Excellence: Develop and improve processes and frameworks that enhance execution, collaboration, and accountability across strategic initiatives