Senior Director, Pricing and Commercial

Flywire•Boston, MA

6d•Hybrid

About The Position

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

Requirements

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

Responsibilities

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
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
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
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
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