Senior Sales Manager, Flywire
CA$120-140k
+ ESPP and commission
More information about location
Global payments processing
Be an early applicant
Global payments processing
1001+ employees
Be an early applicant
CA$120-140k
+ ESPP and commission
More information about location
1001+ employees
Company mission
To improve the payment experience for everyone.
Role
Who you are
- 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
- 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
What the job involves
- 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
- 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
- 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
Application process
- We are excited to get to know you! Throughout our process you can expect to meet different FlyMates 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
Our take
Flywire is a digital platform that simplifies the paying experience for international transactions. Flywire leverages its vertical-specific software and payments technology to deeply embed within client's existing accounts-receivable workflows.
Flywire was first set up to help international students pay their tuition for American colleges, but has since grown into a global payments enablement and software company. It has processed billions of dollars in payments for clients across the world and secured approval for its major payment institution license, enabling it to operate domestic money transfer and cross-border money transfer services.
Flywire serves clients across education, healthcare, travel, and B2B, including several Ivy League schools, and top US hospital systems. The company appears to be focussed on growth, including by strategic acquisitions and entry into new markets, recently in the Asia Pacific and Australia, as well as further developing its channel partners ecosystem.
Steph
Company Specialist at Welcome to the Jungle
Insights
12% employee growth in 12 months
Company
Funding (last 2 of 8 rounds)
Mar 2021
$60m
SERIES F
Feb 2020
$120m
SERIES E
Total funding: $323.2m
Company HQ
Downtown Crossing, Boston, MA
Leadership
Mike Massaro
(CEO)Mike joined Flywire as a VP of Business Development in 2012 before becoming CEO in 2013. Prior to this, he spent 6 years at Carrier IQ as a VP of Strategic Accounts & Corporate Development and Advisor.
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