Senior Sales Manager

Flywire

Senior Sales Executive leading growth strategy for Flywire’s Higher Education sector in Canada. Engaging senior stakeholders and driving revenue in complex environments.

Posted 4/30/2026full-timeRemote • 🇨🇦 CanadaSenior💰 CA$120,000 - CA$140,000 per yearWebsite

About the role

Key responsibilities & impact

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.
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.
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.
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.
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.

Requirements

What you’ll need

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.

Benefits

Comp & perks

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 #InsideFlywire on social media
Dynamic & Global Team (we have been collaborating virtually for years!)
Wellbeing Programs (Mental Health, Wellness, Yoga/Pilates/HIIT Classes) with Global FlyMates
Competitive time off including FlyBetter Days to volunteer in your community and Digital Disconnect Days!
Great Talent & Development Programs (Managers Taking Flight – for new or aspiring managers!)

ATS Keywords

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Applicant Tracking System Keywords

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Hard Skills & Tools

enterprise salesGTM strategyrelationship managementmarket intelligenceconsultative sellingcomplex deal executionbilingual communicationfintechSaaSERP systems

Soft Skills

executive presencestrategic leadershipinfluence capabilitycommunication skillsorganizational skillsrelationship buildingpolitical navigationadaptabilityconsultative approachdiscipline