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Director, People & Culture, Americas

| Greater Boston Area
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Have you imagined working in an environment driven by a passion and desire to not only outperform, but also outbehave the market? Since 2009, Flywire has been that company, creating solutions that break barriers, and teams that always look at the next disruptive way to move Flywire and its customers into the next phase of global payment solutions.

We are seeking an experienced People leader to support our next chapter of growth! This role will be both strategic and hands-on, improving organizational effectiveness and design, leading change management, providing leadership coaching, and driving excellence throughout our organization.

As Flywire’s Director of People & Culture, you will partner with the business (your clients) throughout the planning and execution of FlyMate (employee) programs, tying them back to business strategy and planning. You will also help lead the P&C function, which includes employee relations, internal communications, culture, talent management, organizational change, training and development, operations, and compensation. A successful candidate will connect with FlyMates at all levels, possess excellent communication skills and a strong business acumen, and be excited to collaborate across multiple geographies.

With over 30 nationalities across 9 different offices, and diversity and inclusion at the core of our people agenda, we believe our FlyMates are our greatest asset, and as a member of the Global People & Culture Team, you will help accelerate Flywire across the globe!

Key responsibilities:

  • Work with senior management and the P&C team to develop and implement P&C plans and solutions
  • Partner with the business on organizational design, talent, and skills assessment and development
  • Provide coaching to our managers and senior leadership team
  • Assess training needs and conduct 1:1 and group training sessions as appropriate
  • Review and analyze business metrics including data on retention and FlyMate experience in order to recommend systemic improvements
  • Partner with the business on the talent management process
  • Provide compensation support including salary planning, approval of salary actions, promotions, and job re-leveling
  • Work with people managers and FlyMates to address all types of employee relations issues, fairly representing all interests
  • Work with business groups to assess, create, and implement innovative solutions for a variety of employee engagement initiatives within the client group

FlyMate skills and qualifications:

  • Bachelor's degree or equivalent post-secondary degree in human resources, psychology, or related field
  • 8+ years of experience in a leadership role with knowledge and experience in People & Culture and/or business partner functions
  • Previous employee relations and talent assessment experience
  • Experience with compensation planning, negotiation, and implementation
  • Excellent business acumen
  • An ability and desire to own a space, provide thought leadership, and catalyze results
  • Proficiency in assessing talent
  • Work experience in a scaling start-up
  • Demonstrated achievements in coaching, influencing, and problem solving
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Technology we use

  • Engineering
  • Product
  • Sales & Marketing
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Our office is conveniently located next to the Park Street train stop and overlooks the Boston Common with views of the State House.

An Insider's view of Flywire

How would you describe the company’s work-life balance?

This is a team that has fun and gets the job done. Flexible schedules and generous PTO are huge factors, but Flywire goes beyond that by fostering a fun, family-friendly environment. I love working in an atmosphere where work and friends and family seem to all blend together.


Talent Acquisition Specialist

How does the company support your career growth?

The exposure Flywire gives to all sectors of the business has made the most valuable impact on my career. Working cross-functionally with Flymates from other teams and other countries allowed me to broaden my scope and expand my skills. You learn to be agile and to adapt quickly to change, which has made me a better version of myself as a worker.


Program Manager-Global Partnerships

How do you empower your team to be more creative?

With the many different personalities and styles on my Team, I don’t employ a template for building or maintaining relationships with our partner schools. This 'thinking outside of the box’ approach allows for innovation, imagination, and resourcefulness. As a result, our message is consistent but the delivery is unique and personalized.


Relationship Management Lead - East

What’s the vibe like in the office?

The vibe in the Boston office is ‘work hard, play hard.’ Boston Flymates are extremely passionate about what they do and what they represent, which for me as a relatively new Flymate is so motivating and inspiring. I’ve never worked at a place where its people were so welcoming and always eager to help in any way they can!


Customer Success Associate

What are Flywire Perks + Benefits

Flywire Benefits Overview

Flywire is proud to be one of Built In Boston's 100 Best Places to Work.

Volunteer in local community
Friends outside of work
Eat lunch together
Open office floor plan
Unconscious bias training
Diversity manifesto
Health Insurance & Wellness Benefits
Flexible Spending Account (FSA)
Disability Insurance
Dental Benefits
Life Insurance
Wellness Programs
Onsite Gym
Retirement & Stock Options Benefits
401(K) Matching
Employee Stock Purchase Plan
Child Care & Parental Leave Benefits
Generous Parental Leave
Flexible Work Schedule
Remote Work Program
Family Medical Leave
Vacation & Time Off Benefits
Generous PTO
Paid Holidays
Paid Sick Days
Perks & Discounts
Casual Dress
Commuter Benefits
Company Outings
Game Room
Stocked Kitchen
Some Meals Provided
Happy Hours
Professional Development Benefits
Job Training & Conferences
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