Senior Project Manager
Flywire • Boston, MA1d • $120,000 - $145,000 • Hybrid
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Senior Project Manager
Flywire•Boston, MA
•$120,000 - $145,000•Hybrid
About The Position
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 that will join our growing Enterprise PMO function, requiring strong executive presence, enterprise level experience, influence without authority, and the ability to operate effectively in ambiguity. You will work across a broad range of stakeholders- varying in experience, functional maturity, and change readiness- while driving alignment, clarity, and measurable outcomes.
Requirements
- 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
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
Benefits
- benefits
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What This Job Offers
Job Type
Full-time
Career Level
Senior
Education Level
No Education Listed
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