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Senior Director, Pricing and Commercial

Flywire


Job Location:

Boston, NH - USA

Monthly Salary: Not provided by the employer
Posted: 25 September 2026 (7 hours ago)
Application Deadline: 23 December 2026
Vacancies: 1 Vacancy

Job Summary

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 Flywires 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 Flywires 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 Flywires 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 youll 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

Qualifications :

Heres what were 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.

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 $198000 - $225000. 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


Remote Work :

No


Employment Type :

Full-time


About Company

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Flywire is a global payments enablement and software company, delivering high-stakes, high-value payments across the global education, healthcare, travel and B2B industries. Today, we’ve digitized payments for more than 4,000+ global clients in more than 140 currencies across 240 cou ... View more

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