Senior Account Executive

Flywire; Boston (MA); Remote; USD 120,000 - 150,000; Full time

Job summary

Join a forward-thinking company as an Account Executive, where you'll drive transformative sales in the AR automation space. With a focus on mid-market clients, you'll leverage your expertise to streamline invoicing and payments, making a real impact in the fintech landscape. This role offers the chance to work with a dynamic global team, engage in consultative selling, and enjoy competitive compensation, including stock options. If you're self-motivated and ready to thrive in a fast-paced environment, this opportunity is perfect for you.

Benefits

Restricted Stock Units

Employee Stock Purchase Plan

Global Induction Program

Wellbeing Programs

Competitive Time Off

Talent & Development Programs

Qualifications

• 3-5 years of experience in quota-carrying SaaS sales.
• Proven success selling to finance teams in mid-market organizations.

Responsibilities

• Drive new business by prospecting mid-market companies.
• Manage the full sales lifecycle from lead generation to deal closure.

Skills

SaaS Sales

Consultative Selling

Value-Based Sales Methodology

Negotiation Skills

Presentation Skills

Job 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 3,100 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 1000+ global FlyMates, representing more than 40 nationalities, and in 14 offices world-wide, we’re looking for FlyMates to join the next stage of our journey as we continue to grow.

The Opportunity:
Flywire is seeking a results-driven sales professional with 3–5 years of experience selling mid-market AR automation or Invoice-to-Cash software to join our B2B team. In this role, you’ll be at the forefront of transforming the way businesses manage their receivables, helping clients streamline invoicing, payments, and reconciliation with Flywire’s innovative I2C platform.

As an Account Executive, you’ll own the full sales lifecycle—from lead generation to deal closure—while acting as a trusted advisor to mid-market clients. You’ll leverage your AR automation expertise to articulate Flywire’s value proposition, build long-term partnerships, and drive meaningful outcomes for both our clients and our business.

Key Responsibilities:

• Drive New Business: Prospect and engage mid-market companies to identify needs and position Flywire’s I2C solution as a fit for their AR automation goals.
• Consultative Selling: Act as a strategic advisor, understanding clients' pain points and crafting tailored solutions that deliver operational efficiency and financial ROI.
• Sales Lifecycle Ownership: Manage opportunities end-to-end, including outreach, discovery, demos, proposals, and contract negotiation.
• Cross-Functional Collaboration: Partner with marketing, product, legal, and onboarding teams to ensure successful implementations and a smooth client experience.
• Partnership Growth: Deepen relationships with existing clients and identify expansion opportunities to grow Flywire’s footprint within the account.
• Outbound Engagement: Consistently generate new pipeline through outbound prospecting, industry events, and networking.
  

Here's What We're Looking For:

• 3–5 years of quota-carrying experience in SaaS, preferably in AR automation, Fintech, or Invoice-to-Cash solutions
• Proven success selling to finance teams within mid-market organizations
• Strong consultative selling and value-based sales methodology experience
• Comfortable leading complex sales cycles with multiple stakeholders
• Clear communicator with strong presentation and negotiation skills
• Highly self-motivated, organized, and excited to work in a fast-paced environment

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!
• Great Talent & Development Programs (Managers Taking Flight – for new or aspiring managers!)

The US base salary range for this full-time position is $120,000-$150,000 plus 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.

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 12 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.

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