Senior Product Manager, People Systems

Flywire; Chicago (IL); On-site; USD 142,000 - 177,000; Full time

Benefits offered by this job

ESPP

Digital Disconnect

FlyBetter Days

Wellbeing Programs

Job summary

Flywire is seeking an experienced Sr. Product Manager focused on internal Human Capital Management systems like Workday. You will lead complex enterprise initiatives, partner with senior leaders, and mentor teams to evolve our platforms as Flywire grows.

You'll own significant platform areas, drive strategy, ensure scalable, secure architectures, and champion Agile practices across teams while influencing governance forums.

Qualifications

• Bachelor's degree in Information Systems, Business, or a related field.
• 5+ years of product management experience in enterprise technology.
• Proven success leading cross-functional product initiatives from strategy to delivery.
• Deep understanding of enterprise platform ecosystems (e.g., Salesforce, Workday, integration platforms).
• Strong executive communication skills with experience presenting to senior leadership and C-suite stakeholders.
• Experience with Agile at scale and guiding teams on product best practices.

Responsibilities

• Define, own, and execute the product strategy and multi-year roadmap for significant enterprise system areas, aligning with company-wide objectives.
• Partner directly with senior business leaders and executives to identify and prioritize high-value technology investments.
• Translate complex, ambiguous business challenges into well-defined product requirements and actionable engineering plans.
• Lead cross-functional teams through the full product development lifecycle, from discovery and design through launch and continuous improvement.
• Establish and govern product metrics frameworks, using data and analytics to drive informed decision-making and demonstrate business value.
• Drive platform architecture discussions, influencing technical decisions to ensure scalability, security, and long-term sustainability.
• Champion Agile best practices and lead the adoption of product management methodologies across teams.
• Manage and mentor junior and mid-level Product Managers, providing coaching, feedback, and development opportunities.
• Represent product management in enterprise architecture reviews and governance forums.
• Build and maintain strong relationships with key vendors, evaluating platform capabilities and negotiating roadmap commitments.

Skills

Enterprise product leadership

Cross-functional leadership

Agile at scale

Data analysis

Mentoring

Education

Bachelor's degree in Information Systems, Business, or related field

Tools

Salesforce

Workday

Integration platforms

Job description

Are you ready to trade your job for a journey? Become a FlyMate!

Passion, excitement & global collaboration are all core to what it means to be a FlyMate. At Flywire, we’re on a mission to deliver the world’s most important and complex payments. We use our Flywire Advantage - the combination of our next-gen payments platform, proprietary payment network and vertical specific software, to help our clients get paid, and help their customers pay with ease - no matter where they are in the world.

What more do we need to truly be unstoppable? Perhaps, that is you!

Who we are: Flywire is a global payments enablement and software company, founded more than a decade ago to solve high-stakes, high-value payments in higher education. We’ve since scaled into new regions and industry verticals and expanded our product offerings to deliver meaningful value to our clients around the world.

Today we support more than 5,300 clients across the global education, healthcare, travel & B2B industries, with diverse payment methods across 240 countries & territories and more than 140 currencies.

With over 1,400+ global FlyMates, representing more than 40 nationalities, and in 15 offices world-wide, we’re looking for FlyMates to join the next stage of our journey as we continue to grow.

Are you ready to trade your job for a journey? Become a FlyMate!

Passion, excitement & global collaboration are all core to what it means to be a FlyMate. At Flywire, we’re on a mission to deliver the world’s most important and complex payments. We use our Flywire Advantage - the combination of our next-gen payments platform, proprietary payment network and vertical specific software, to help our clients get paid, and help their customers pay with ease - no matter where they are in the world.

What more do we need to truly be unstoppable? Perhaps, that is you!

Who we are: Flywire is a global payments enablement and software company, founded more than a decade ago to solve high-stakes, high-value payments in higher education. We’ve since scaled into new regions and industry verticals and expanded our product offerings to deliver meaningful value to our clients around the world.

Today we support more than 5,300 clients across the global education, healthcare, travel & B2B industries, with diverse payment methods across 240 countries & territories and more than 140 currencies.

With over 1,400+ global FlyMates, representing more than 40 nationalities, and in 15 offices world-wide, we’re looking for FlyMates to join the next stage of our journey as we continue to grow.

Job Description

The Opportunity

We, at Flywire, are looking for an experienced Sr. Product Manager with a focus on internal Human Capital Management (HCM) systems, such as Workday, ideally with a background in FinTech. At this advanced career level, you will lead complex product initiatives across our enterprise systems portfolio, driving strategic outcomes and mentoring team members.

You will own significant platform areas, partner directly with senior business leaders, and ensure that our enterprise systems continuously evolve to support Flywire's growth and competitive position. This role demands deep technical knowledge, executive presence, and the ability to influence across the organization.

Key Responsibilities

• Define, own, and execute the product strategy and multi-year roadmap for significant enterprise system areas, aligning with company-wide objectives.
• Partner directly with senior business leaders and executives to identify and prioritize high-value technology investments.
• Translate complex, ambiguous business challenges into well-defined product requirements and actionable engineering plans.
• Lead cross-functional teams through the full product development lifecycle, from discovery and design through launch and continuous improvement.
• Establish and govern product metrics frameworks, using data and analytics to drive informed decision-making and demonstrate business value.
• Drive platform architecture discussions, influencing technical decisions to ensure scalability, security, and long-term sustainability.
• Champion Agile best practices and lead the adoption of product management methodologies across teams.
• Manage and mentor junior and mid-level Product Managers, providing coaching, feedback, and development opportunities.
• Represent product management in enterprise architecture reviews and governance forums.
• Build and maintain strong relationships with key vendors, evaluating platform capabilities and negotiating roadmap commitments.

Qualifications

Here’s What We’re Looking For

• Bachelor's degree in Information Systems, Business, or a related field.
• 5+ years of experience in product management with a focus on enterprise technology systems.
• Demonstrated success leading high-impact, cross-functional product initiatives from strategy to delivery.
• Deep understanding of enterprise platform ecosystems (e.g., Salesforce, Workday, integration platforms).
• Strong executive communication skills with experience presenting to senior leadership and C-suite stakeholders.
• Proven ability to influence without authority and drive alignment across diverse stakeholder groups.
• Experience with Agile at scale and guiding teams on product best practices.
• Analytical mindset with strong skills in data analysis, modeling, and business case development.
• Experience managing indirect team members and mentoring product professionals.

Preferred Qualifications

• Experience in FinTech, payments, or global B2B platforms.
• Experience managing product portfolios spanning multiple geographies.
• Familiarity with AI/ML, agentic AI, or advanced automation within enterprise platforms.
• Product management certifications (CSPO, SAFe, or equivalent).

Additional Information

What We Offer

• Competitive compensation
• Employee Stock Purchase Plan (ESPP)
• Competitive time off, including Digital Disconnect and FlyBetter Days to volunteer in a cause you believe in.
• Work with brilliant people globally Learn more about their journeys by checking out #InsideFlywire on social media
• Wellbeing Programs (Mental Health, Wellness, Yoga/Pilates/HIIT Classes) with Global FlyMates
• Be a meaningful part in our success - every FlyMate makes an impact
• Great Talent & Development Programs (Managers Taking Flight – for new or aspiring managers, OneFlywire Career Mobility)

The US base salary range for this full-time position is $142,000-$177,000 plus equity and benefits. Our salary ranges are determined by role, position level, and location. The range displayed on this job posting reflects the minimum and maximum target for new hire salaries for the position across all US locations. Within the range, individual pay is determined by work location and several other factors, including job-related skills, experience, relevant education and training.

Flywire is an equal opportunity employer and follows a policy of administering all employment decisions and personnel actions without regard to race, color, religion, sex, pregnancy, gender identity, national origin, age, ancestry, physical or mental disability, sexual orientation, genetic disposition or carrier status, veteran status, or any other category protected under applicable national, federal, state or local law.