Senior Director, Pricing and Commercial

About the role

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

Additional information

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
• Additional Information: Submit today and get started!

• 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.

Pay and benefits

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.

#LI-Hybrid