Jobs · Massachusetts

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.

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