The Opportunity

Flywire is a global payments enablement and software company focused on solving high-value, complex payments for clients worldwide. We are seeking a highly seasoned, Senior Sales Executive to lead Flywire’s Higher Education growth strategy across Québec and Atlantic Canada— with Québec as the primary strategic priority. This position can be based in Quebec, Ontario, or Atlantic Canada.

This role is designed for a senior leader who brings deep experience in the education sector and understands how to influence outcomes through trusted relationships, partnerships, sector associations, and institutional credibility. Beyond driving revenue, the successful candidate will elevate Flywire’s presence by engaging senior stakeholders, aligning with Provincial political and educational realities, and positioning Flywire as a long-term strategic partner—not simply a technology vendor.

Primary Responsibilities:

Strategic Market Leadership (Québec-Focused)

• Develop and execute a GTM strategy rooted in cultural fluency, regional insight, and localized value articulation.
• Establish Flywire as a trusted institutional partner by leveraging long-standing sector relationships and credibility within the education network.
  Navigate governance structures, procurement frameworks, and political nuances unique to Québec’s higher education landscape.

Relationship Development, Partnerships & Ecosystem Integration

• Build and maintain influential, senior-level relationships with Presidents, CFOs, CIOs, Registrars, Finance, IT, Student Services, and Executive Leadership across universities, CEGEPs, and colleges.
• Serve as Flywire’s senior market presence in the market, acting as a respected advisor, connector, and trusted industry voice.
  Proactively leverage partners, consultants, industry associations, coordination bodies, and policy stakeholders to expand access, strengthen influence, and accelerate credibility.

Sales Execution & Revenue Leadership

• Lead regional enterprise sales strategy to deliver sustained revenue growth across Québec and Atlantic Canada.
• Manage complex, multi-stakeholder enterprise sales cycles from discovery to close in both French and English.
• Align Flywire’s value proposition to markets institutional priorities, ensuring solutions meet operational, policy, and student experience needs.
  Build, forecast, and convert a robust institutional pipeline.

Market Engagement & Brand Authority

• Represent Flywire as a senior industry presence at major education conferences, institutional roundtables, and leadership forums.
• Cultivate Flywire’s reputation through thought leadership, relationship building, and strategic sector engagement.
  Engage Provincial-based influencers and partners when beneficial to enhance brand visibility and institutional access.

Internal Collaboration

• Work closely with Product, Payments & Pricing, Technology, Legal, Compliance, and Marketing to support complex enterprise deal execution.
• Provide strategic market intelligence on trends, competitive environment, regulatory developments, and institutional needs.
• Ensure seamless transition and success with Implementation and Relationship Management teams post-sale.

Here's what we're looking for

• Bilingual
• Professional Proficiency French and English.
• 10-15 years experience in Canadian higher education, ERPs, fintech, payments, banking, SaaS, or enterprise technology.
• Proven success leading senior-level enterprise sales engagements and closing complex, multi-stakeholder deals.
• Demonstrated ability to operate effectively in relationship-driven, politically influenced, and institutionally complex environments.
• Exceptional executive presence, communication, and consultative selling skills in both languages.
• Strategic, credible, and trusted leader with demonstrated influence capability.
• Highly organized, disciplined, and effective in a fast-paced, growth-oriented environment.
  Ability to travel extensively within Québec and Atlantic Canada.

What We Offer:

• Competitive compensation
• Employee Stock Purchase Plan (ESPP)
• Flying Start
• Our immersive Global Induction Program (Meet our Execs & Global Teams)
• Work with brilliant people that will keep you on your toes, learn more about their journeys by checking out #Inside Flywire on social media
• Dynamic & Global Team (we have been collaborating virtually for years!)
• Wellbeing Programs (Mental Health, Wellness, Yoga/Pilates/HIIT Classes) with Global Fly Mates
• Competitive time off including Fly Better Days to volunteer in your community and Digital Disconnect Days!
• Great Talent & Development Programs (Managers Taking Flight – for new or aspiring managers!)

Submit today and get started!

We are excited to get to know you! Throughout our process you can expect to meet different Fly Mates including the Hiring Manager and other Flymates. Your Talent Acquisition Partner will walk you through the steps and be your “go-to” person for questions.

Flywire is an equal opportunity employer. With over 40 nationalities across 12 different offices, and diversity and inclusion at the core of our people agenda, we believe our Fly Mates are our greatest asset, and we’re excited to watch our unique culture evolve with each new hire.

The US base salary range for this full-time position is $120,000-$140,000 CAD plus commission and benefits. Our salary ranges are determined by role, position level, and location. The range displayed on this job posting reflects the minimum and maximum target for new hire salaries for the position across all US locations. Within the range, individual pay is determined by work location and several other factors, including job-related skills, experience, relevant education and training.

Are you ready to trade your job for a journey? Become a Fly Mate!

Passion, excitement & global collaboration are all core to what it means to be a Fly Mate. At Flywire, we’re on a mission to deliver the world’s most important and complex payments. We use our Flywire Advantage - the combination of our next-gen payments platform, proprietary payment network and vertical specific software, to help our clients get paid, and help their customers pay with ease - no matter where they are in the world.

What more do we need to truly be unstoppable? Perhaps, that is you!

Who we are:

Flywire is a global payments enablement and software company, founded more than a decade ago to solve high-stakes, high-value payments in higher education. We’ve since scaled into new regions and industry verticals and expanded our product offerings to deliver meaningful value to our clients around the world.

Today we support more than 4,800 clients across the global education, healthcare, travel & B2B industries, with diverse payment methods across 240 countries & territories and more than 140 currencies.

With over 1,200 global Fly Mates, representing more than 40 nationalities, and in 12 offices world-wide, we’re looking for Fly Mates to join the next stage of our journey as we continue to grow.