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VP, Revenue Operations

Company Description

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

Passion, excitement & global collaboration are all core to what it means to be a FlyMate. 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 a decade ago to solve high-stakes, high-value payments in education, using modern technology.

Today, we’ve digitized payments for more than 3,800+ global clients across education, healthcare, travel & B2B, covering more than 240 countries and territories and supporting over 140 currencies. And, we’re just getting started!

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

Job Description

Are you a visionary leader, passionate about revolutionizing global revenue operations in a dynamic environment? Flywire is seeking a strategic and hands-on senior leader to drive and orchestrate our entire revenue generation lifecycle, from initial awareness to sustained customer expansion and retention. This is not just a leadership role; it's an opportunity to help shape the future of a rapidly growing company.

Your Impact:

You will be the driving force behind our sales, marketing and customer success engine, leading a team responsible for mission-critical programs across:

  • Marketing & Sales Operations: Streamlining processes, optimizing lead generation, and driving sales efficiency to achieve our pipeline, ARR, revenue growth and retention goals 
  • Proposals & Deal Management: Architecting compelling proposals and optimizing deal flow to accelerate revenue.
  • Go-to-Market Readiness & Effectiveness: Equipping our teams with the tools, training, and insights they need to succeed
  • Sales Commission & Incentive Strategies: Designing and implementing performance-driven incentive programs
  • Go-to-Market Technology: Partnering with our Systems team, you’ll own our tech stack vision and roadmap (Gong, Marketo, etc.), ensuring seamless integration into our CRM, and driving innovation

You'll be a key strategic partner, collaborating directly with Sales, Customer Success, Marketing, Business Operations, and Finance to define strategy, implement performance metrics, and drive alignment across all revenue-generating functions.

Why Flywire?

  • Strategic Influence: You'll play a pivotal role in shaping Flywire's global growth strategy.
  • Transformative Leadership: You'll lead a high-performing team and drive significant operational improvements.
  • Innovation & Impact: You'll have the opportunity to build and implement cutting-edge RevOps solutions.
  • Global Reach: You'll impact revenue generation across diverse verticals worldwide.
  • Dynamic Environment: You'll thrive in a fast-paced, collaborative, and innovative culture.

Key Responsibilities:

  • Strategic Partnership: Collaborate with global sales and senior leadership to achieve growth objectives (pipeline, sales ramp, LTV/CAC, ARR, marketing effectiveness and more!) and drive GTM alignment 
  • Operational Excellence: Lead all aspects of sales and marketing operations, optimizing processes and technology
  • Performance Management: Establish and maintain rigorous operating cadence, ensuring accurate forecasting and pipeline management across Flywire's global sales and vertical teams
  • Revenue Innovation: Propose and execute new processes, sales incentives, metrics to help us grow and scale across all verticals 
  • Tech Stack Vision & Ownership: Partner with Systems teams to evaluate, scope, and implement CRM/GTM tech stack enhancements.
  • Data-Driven Insights: Define key metrics, build performance dashboards, and drive data-informed decisions.
  • Change Management: Lead process improvements and drive operational efficiencies across GTM organizations.
  • Executive Support: Support executive deliverables, including Board Reviews and strategic planning.

Qualifications

  • 10–15+ years of RevOps, Sales/Marketing Ops, or GTM Strategy experience in high-growth B2B SaaS environments.
  • A hands-on mindset — you’re not afraid to get into the weeds and make systems, processes, and dashboards better.
  • Track record of building scalable GTM infrastructure from the ground up or through major transformation.
  • Expertise with tools like Salesforce, Marketo, Gong, and other RevOps platforms.
  • Strong analytical chops — you can turn data into insight and insight into action.
  • Experience managing cross-functional projects and driving alignment across Sales, Marketing, Customer Success, and Finance.
  • Outstanding executive communication skills, especially around performance metrics and board-level reporting.
  • A passion for mentoring and building high-performing teams.

Join Flywire and architect our next stage of growth! Apply now.

 

Additional Information

What We Offer:

  • Competitive compensation, including Restricted Stock Units 
  • 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 
  • Be a meaningful part in our success - every FlyMate makes an impact
  • Competitive time off including FlyBetter Days to volunteer in a cause you believe in and Digital Disconnect Days!
  • Work From Home Stipend 
  • 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 with different FlyMates including the Hiring Manager, Peers on the team, the VP of the department, and a skills assessment. Your Talent Acquisition Partner will walk you through the steps and be your “go-to” person for any questions.

Flywire is an equal opportunity employer. With over 40 nationalities across 14 different offices, and diversity and inclusion at the core of our people agenda, we believe our FlyMates 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 $225,000 - $290,000 plus [other potential items: bonus, commission, restricted stock units] 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. Your Talent Acquisition Partner can share more about the specific salary range for your preferred location during the hiring process.

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CEO of Flywire
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Mike Massaro
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Average salary estimate

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$225000K
$290000K

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What You Should Know About VP, Revenue Operations, Flywire

At Flywire, we are thrilled to announce an exciting opportunity for a VP of Revenue Operations to join our dynamic team in Boston, Massachusetts. If you're a visionary leader who is passionate about reshaping global revenue operations, look no further! As the VP, Revenue Operations, you'll be at the helm of our revenue generation lifecycle, collaborating with various teams to drive sales, marketing, and customer success initiatives. Your role is not just a leadership position; it's a chance to shape the future of Flywire by streamlining processes, optimizing lead generation, and ensuring our revenue goals are met and exceeded. You'll lead a talented team, enhancing our approaches to proposals, sales commission strategies, and go-to-market readiness. With tools like Salesforce and Marketo at your disposal, you’ll own our tech stack vision, driving innovation within the company. This is your chance to make a profound impact in a fast-paced, collaborative environment full of passionate FlyMates who are dedicated to making complex payments seamless for our customers around the globe. Come discover what it means to be a FlyMate and help us achieve monumental success together!

Frequently Asked Questions (FAQs) for VP, Revenue Operations Role at Flywire
What are the key responsibilities of the VP, Revenue Operations at Flywire?

The VP, Revenue Operations at Flywire plays a critical role in overseeing the entire revenue generation lifecycle. Key responsibilities include streamlining sales and marketing processes, optimizing lead generation, analyzing performance metrics, and managing deal flow. This role directly impacts how Flywire aligns its sales, marketing, and customer success efforts to achieve revenue goals.

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What qualifications do I need to become a VP, Revenue Operations at Flywire?

To qualify for the VP, Revenue Operations role at Flywire, candidates typically need 10–15+ years of experience in RevOps or GTM strategy, specifically in high-growth B2B SaaS environments. A hands-on mindset, expertise in tools like Salesforce and Marketo, and a proven record of building scalable revenue operations infrastructure are crucial. Strong analytical and communication skills are also essential.

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How does the VP, Revenue Operations contribute to Flywire's growth strategy?

The VP, Revenue Operations at Flywire is integral to shaping the company's growth strategy by collaborating with senior leadership to achieve critical objectives related to pipeline, sales efficiency, and customer success. This role involves implementing innovative revenue strategies that enhance Flywire’s market positioning and overall performance.

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What types of tools will the VP, Revenue Operations use at Flywire?

As the VP, Revenue Operations at Flywire, you will leverage advanced tools such as Salesforce, Marketo, and Gong to streamline operations and ensure seamless integration into our systems. Familiarity with these technologies will be essential in driving the performance and efficacy of the revenue generation workflow.

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What makes Flywire a great place to work as a VP, Revenue Operations?

Flywire offers an engaging and innovative environment where you can significantly impact global revenue operations. As a VP, you will be leading a high-performing team and working on transformative projects that offer strategic influence and opportunities for career development. We foster a dynamic culture that values diversity and collaboration, ensuring every FlyMate thrives.

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Common Interview Questions for VP, Revenue Operations
Can you explain your experience with revenue operations in a B2B SaaS environment?

In responding to this question, emphasize your experience leading revenue operations teams, specifying relevant metrics you improved and initiatives you implemented. Highlight your deep understanding of the SaaS business model and how your strategic efforts drove measurable revenue growth.

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How do you prioritize initiatives across sales, marketing, and customer success?

When answering this, discuss your data-driven approach to prioritizing initiatives. Share how you assess the potential impact on revenue, operational efficiency, and customer satisfaction, while also mentioning any frameworks or tools you utilize to facilitate this prioritization.

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Describe a time when you led a significant change in revenue operations.

To answer this question effectively, narrate a high-impact project you managed. Focus on the change process, your leadership approach, and the outcomes achieved. Be specific about challenges faced and how you overcame them, demonstrating your ability to lead through transformational periods.

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What approaches do you take to ensure alignment between sales and marketing teams?

Explain your strategies for fostering collaboration between sales and marketing. Include practices such as regular joint meetings, shared metrics, and integrated tech stacks that promote transparency and unified goals, highlighting the importance of communication and teamwork.

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How do you utilize data analytics to drive revenue strategy?

Discuss your proficiency in leveraging data analytics tools to gather insights that inform revenue strategy. Provide examples of how you’ve used data to make informed decisions, optimize sales processes, and track performance, which subsequently enhanced revenue generation.

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What metrics do you consider most important in revenue operations?

Identify key performance indicators such as customer acquisition cost (CAC), lifetime value (LTV), churn rate, and sales efficiency ratios. Explain why these metrics are significant and how tracking them can lead to improved revenue performance and strategic decision-making.

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Can you give an example of a successful go-to-market strategy you devised?

Share a specific instance where you created and executed a go-to-market strategy, elucidating the thought process behind it, the execution plan, and the results achieved. Highlight any metrics that illustrate the success of your strategy and any lessons learned in the process.

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How do you approach mentoring and developing your team?

Discuss your mentorship philosophy, emphasizing the importance of fostering an environment of growth and learning. Share actionable methods you use to develop team members, such as regular feedback, professional development opportunities, and personalized growth plans.

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What challenges do you foresee in the role of VP of Revenue Operations, and how would you address them?

Address potential challenges like market fluctuations or internal resistance to change. Discuss your proactive approach to anticipating challenges and your readiness to adapt strategies, employing cross-functional collaboration to tackle issues effectively.

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How do you ensure the adoption of new technologies within your team?

To effectively answer this question, explain your change management strategies. Discuss the importance of training, user feedback, and ongoing support in ensuring technology adoption. Give examples of previous successes in implementing new tools and processes.

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Flywire ensures organizations deliver on their customers’ most important moments.

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BENEFITS & PERKS
Dental Insurance
Disability Insurance
Vision Insurance
Performance Bonus
Paid Holidays
FUNDING
SENIORITY LEVEL REQUIREMENT
TEAM SIZE
EMPLOYMENT TYPE
Full-time, on-site
DATE POSTED
April 10, 2025

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