Senior Project Manager

Flywire•Boston, MA

1d•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 role 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