Senior Director, Pricing and Commercial

Flywire; Massachusetts; Hybrid; USD 198,000 - 225,000; Full time

Job summary

Flywire is seeking a senior pricing and commercial growth leader to own global software pricing, packaging, and contracting across multiple verticals. You will partner with Strategy, Product, Sales, and Finance to drive value-based pricing, discounts governance, and scalable monetization strategies.

The role focuses on driving ACV growth, margin improvement, and deal velocity while aligning pricing with strategic roadmaps and long-term portfolio value across US locations.

Qualifications

• 12+ years of experience in pricing, monetization, GTM strategy, corporate strategy, within a B2B SaaS or platform company.
• Proven ownership of pricing and packaging for multi-product organizations.
• Strong understanding of value-based pricing, tiered and usage-based models, and complex deal structures.

Responsibilities

• Own Flywire’s global software pricing, packaging, and contracting strategy across products, verticals, and customer segments.
• Partner with Strategy/BizOps, Product, Sales to align pricing with roadmap decisions and launches.
• Drive ACV growth, price realization, and margin uplift through disciplined pricing execution.
• Lead pricing for new software products, expansions, and major commercial initiatives.
• Establish discount discipline and governance to scale across teams.
• Provide governance on complex enterprise deals.

Skills

Pricing strategy

Monetization

GTM strategy

Corporate strategy

Value-based pricing

Contracting models

Analytical ability

Executive influence

Communication

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 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 5,300 clients across the global education, healthcare, travel & B2B industries, with diverse payment methods across 240 countries & territories and more than 140 currencies.

With over 1,400 global FlyMates, representing more than 40 nationalities, and in 15 offices world-wide, we’re looking for FlyMates to join the next stage of our journey as we continue to grow.

Why this role matters

As Flywire scales a multi-product software platform across verticals, regions, and buyer types, software pricing and contracting become some of the most powerful levers for growth, consistency, and long-term value creation. The Director of Pricing & Commercial Growth drives Flywire’s software pricing strategy and commercial frameworks across verticals. This role ensures we win deals while capturing the full value of what we deliver, balancing growth acceleration with margin discipline and scalability.

This is a senior commercial leadership role. It helps to set direction, defines guardrails, and shapes how value is captured across the business.

What this role exists to do

Own Flywire’s global software pricing, packaging, and contracting strategy, translating product value and market insight into scalable commercial models. Partner closely with Corporate Strategy/BizOps and transactional/payex pricing teams to ensure a cohesive, value-driven monetization approach across software and payments.

Key Responsibilities: Pricing & Packaging Strategy

• Own Flywire’s software pricing and packaging strategy across products, verticals, and customer segments
• Design value-based pricing models, bundles, and offers aligned to customer outcomes and willingness to pay
• Define pricing frameworks including list prices, floors, guardrails, and discount thresholds by product and segment
• Partner with Strategy/BizOps, Product and Product Marketing, Sales to align pricing with roadmap decisions, positioning, and launches
• Lead pricing strategy for new software products, expansions, and major commercial initiatives

Contracting & Deal Structure

• Own commercial deal structures and contracting strategy in close partnership with Legal
• Develop standard contract templates and commercial terms that cover the majority of deals and accelerate deal velocity
• Establish deal governance that balances Sales flexibility with margin protection and long-term portfolio value
• Provide oversight on complex, high-value, or non-standard enterprise deals

Value Growth & Governance

• Drive ACV/average deal size growth, price realization, and margin uplift through disciplined pricing execution
• Establish discount discipline and approval frameworks that scale
• Define and monitor pricing KPIs including ACV, margin, price realization, deal velocity, and exception rates
• Use win/loss and deal data to continuously refine pricing and packaging strategies

Customer, Market & Data Insight

• Lead pricing-specific customer and market research, including quantitative pricing studies when appropriate
• Analyze usage, deal, and market data to identify pricing opportunities, risks, and tradeoffs
• Translate insight into clear recommendations and decision points for executive leadership

Cross-Functional Leadership

• Partner with Sales, Revenue Operations, Finance, Product, and Product Marketing to operationalize pricing strategy
• Present pricing recommendations, scenarios, and tradeoffs to senior leadership and the executive team
• Partner closely with FP&A & Corporate Strategy/BizOps to align pricing with long-term growth and portfolio strategy
• Work in tight collaboration with transactional/payment pricing teams to align software pricing with payment economics
• This role defines the strategy, frameworks, and guardrails that others execute within.

What this role does not own or do

• Marketing messaging or campaign execution
• Product roadmap ownership
• Product strategy or bizops/corporate strategy
• Make pricing decisions in a silo - this is a collaborative process involving CCO, field (GMs, verticals) COO, transactional pricing, Finance

How success is measured

• Sustained deal size/ACV growth and margin improvement across software products
• Consistent pricing execution with reduced deal exceptions
• Improved deal velocity through standardized contracting
• Adoption of pricing frameworks by Sales and GTM teams
• Executive confidence in pricing decisions and governance
• Who you’ll work closely with
• Exec team, Vertical GMs, Corporate Strategy/BizOps, Product Management, Product Marketing, Sales and RM leadership, Revenue Operations, Finance, Legal, Transactional Pricing teams

Here’s what we’re looking for

• 12+ years of experience in pricing, monetization, GTM strategy, corporate strategy, within a B2B SaaS or platform company
• Proven ownership of pricing and packaging for multi-product, software organizations
• Strong understanding of value-based pricing, tiered and usage-based models, and complex deal structures
• Experience building scalable pricing frameworks, governance, and contracting models
• Strong analytical capability paired with sound commercial judgment
• Ability to influence senior leaders and drive alignment across functions
• Clear, confident communicator who can navigate complexity without over-engineering

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.

Flywire is an equal opportunity employer and follows a policy of administering all employment decisions and personnel actions without regard to race, color, religion, sex, pregnancy, gender identity, national origin, age, ancestry, physical or mental disability, sexual orientation, genetic disposition or carrier status, veteran status, or any other category protected under applicable national, federal, state or local law.

The US base salary range for this full-time position is $198,000 - $225,000. 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.

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