Senior Project Manager
Flywire · Boston, MA · 2 wk ago
Hybrid$120k–$145k/yrFull-time
About the Role
We are seeking a Senior Project Manager with deep business transformation experience to lead complex, cross-functional initiatives that drive meaningful change across the organization. This role partners closely with a Program Manager in a highly collaborative “lock-step” model, forming a dynamic leadership duo that ensures strategy translates into execution. This is a senior individual contributor role within our growing Enterprise PMO function, requiring strong executive presence, enterprise-level experience, influence without authority, and the ability to operate effectively in ambiguity.
Responsibilities
- Lead end-to-end delivery of complex business transformation initiatives across functions
- Partner closely with a Program Manager to align on strategic direction, sequencing, and cross-program dependencies when applicable
- Influence stakeholders at all levels, including senior leadership, through clear recommendations and structured decision-making
- Drive outcomes in environments with competing priorities and shifting expectations
- Proactively identify, assess, and manage risks and cross-functional dependencies
- Translate ambiguity into clear direction, structured plans, and focused execution
- Filter and prioritize effectively—ensuring teams are focused on the highest-impact work
- Tailor communication approaches to different audiences, particularly in transformation settings where messaging, alignment, and change adoption are critical
- Facilitate difficult conversations, align conflicting viewpoints, and maintain forward momentum
- Provide informal mentorship and guidance to Project Managers, elevating delivery standards and consistency across the PMO
- Ensure measurable results and accountability throughout the lifecycle of initiatives
Qualifications
- 10+ years of project management experience, including significant business transformation work
- Demonstrated success leading complex, cross-functional initiatives in evolving or high-growth environments
- Strong executive presence with the ability to “read the room” and adjust approach accordingly
- Expertise in risk and dependency management across multiple stakeholder groups
- Comfort operating in ambiguity and shaping direction where frameworks may not yet exist
- Big-picture thinker who connects dots across initiatives and asks the right strategic questions
- Strong prioritization instincts and judgment
- Excellent written and verbal communication skills, with the ability to tailor messaging for different levels of the organization
- Flexible leadership style—able to adjust approach without compromising outcomes
- Confidence to make recommendations and guide decision-making
- Ability to operate autonomously while maintaining strong partnership and alignment
Pay
The US base salary range for this full-time position is $120,000-$145,000 plus benefits.