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Salary: USD 198,000 - 225,000 / annual
Flywire is a global payments enablement and software company serving over 5,300 clients across education, healthcare, travel, and B2B industries. As Senior Director of Pricing and Commercial, you will own Flywire's global software pricing, packaging, and contracting strategy across multiple verticals and customer segments.
This is a senior commercial leadership role responsible for setting direction, defining guardrails, and shaping how value is captured across the business. You will translate product value and market insights into scalable commercial models while partnering closely with Corporate Strategy, BizOps, and transactional pricing teams.
Key responsibilities include:
**Pricing & Packaging Strategy**: Own software pricing and packaging across products, verticals, and segments. Design value-based pricing models, bundles, and offers aligned to customer outcomes. Define pricing frameworks including list prices, floors, guardrails, and discount thresholds. Partner with Strategy, Product, Product Marketing, and Sales on pricing alignment with roadmap decisions and launches. Lead pricing strategy for new products and major commercial initiatives.
**Contracting & Deal Structure**: Own commercial deal structures and contracting strategy in partnership with Legal. Develop standard contract templates and terms that accelerate deal velocity. Establish deal governance balancing Sales flexibility with margin protection. Provide oversight on complex, high-value, or non-standard enterprise deals.
**Value Growth & Governance**: Drive ACV and average deal size growth, price realization, and margin uplift through disciplined execution. Establish 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 strategies.
**Customer, Market & Data Insight**: Lead pricing-specific customer and market research, including quantitative pricing studies. Analyze usage, deal, and market data to identify opportunities and risks. Translate insights into clear recommendations for executive leadership.
**Cross-Functional Leadership**: Partner with Sales, Revenue Operations, Finance, Product, and Product Marketing to operationalize pricing strategy. Present recommendations and scenarios to senior leadership. Align pricing with long-term growth and portfolio strategy. Collaborate with transactional/payment pricing teams.
Success is measured by sustained ACV growth and margin improvement, consistent pricing execution with reduced exceptions, improved deal velocity through standardized contracting, adoption of frameworks by Sales and GTM teams, and executive confidence in pricing decisions.
You will work closely with the executive team, Vertical GMs, Corporate Strategy/BizOps, Product Management, Product Marketing, Sales and RM leadership, Revenue Operations, Finance, Legal, and Transactional Pricing teams.
**Requirements**:
- 12+ years of experience in pricing, monetization, GTM strategy, or corporate strategy within B2B SaaS or platform companies
- 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 cross-functional alignment
- Clear, confident communicator who can navigate complexity without over-engineering
