Senior Director, Pricing and Commercial

Flywire • Boston, MA

7d • $146,061 - $208,659

About The Position

The Senior Director, Pricing and Commercial owns Flywire’s global software pricing, packaging, and contracting strategy. The role translates product value and market insight into scalable commercial models across products, verticals, and customer segments, partnering with Corporate Strategy/BizOps and transactional/payment pricing teams to coordinate a value-driven approach across software and payments. This senior commercial leadership role sets direction and establishes frameworks and guardrails that enable the business to capture value while supporting growth, margin discipline, and scalability.

The position designs value-based pricing models, bundles, offers, pricing frameworks, and commercial deal structures; develops standard contract templates and terms in partnership with Legal; and provides oversight for complex, high-value, or non-standard enterprise deals. It monitors pricing performance and uses customer, market, usage, and deal insights to refine strategy. The role works cross-functionally with Sales, Revenue Operations, Finance, Product, Product Marketing, Legal, senior leadership, and other teams to operationalize pricing and present recommendations and tradeoffs.

Success is measured by sustained deal-size and ACV growth, margin improvement, consistent pricing execution with fewer exceptions, faster deal velocity through standardized contracting, adoption of pricing frameworks by Sales and GTM teams, and executive confidence in pricing decisions and governance. The role does not own marketing messaging or campaign execution, product roadmap ownership, or product/corporate strategy, and pricing decisions are made collaboratively rather than in a silo.

Requirements

• 12+ years of experience in pricing, monetization, go-to-market strategy, or 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 communication skills and ability to 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 with 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, Product Marketing, and 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 partnership with Legal.
• Develop standard contract templates and commercial terms to cover most 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 and average deal-size growth, price realization, and margin uplift through disciplined pricing execution.
• Establish scalable discount discipline and approval frameworks.
• Define and monitor pricing KPIs, including ACV, margin, price realization, deal velocity, and exception rates.
• Use win/loss and deal data to 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 insights 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 with FP&A and Corporate Strategy/BizOps to align pricing with long-term growth and portfolio strategy.
• Collaborate with transactional/payment pricing teams to align software pricing with payment economics.

Benefits

• Competitive compensation
• Employee Stock Purchase Plan (ESPP)
• Competitive time off
• Wellbeing programs, including mental health and wellness offerings and Yoga/Pilates/HIIT classes
• Talent and development programs, including Managers Taking Flight and OneFlywire Career Mobility

What This Job Offers

• Job Type: Full-time
• Career Level: Senior
• Education Level: No Education Listed