Senior Director, Reward, Performance and Analytics

Company Description

We’re Checkout.com. You might not know our name, but companies like eBay, Spotify, Klarna, Uber, and Sony do, because we’re behind many of the digital experiences you use every day.

We are where the world checks out, enabling over 10 billion transactions yearly for more than one billion global shoppers.

Whether you want to book a holiday, order food, renew a subscription, or check out online, there’s a good chance our tech powers the payments behind the scenes. Our platform helps the most ambitious businesses deliver effortless digital experiences, at scale.

If you want to do career-defining work, you’ve come to the right place. We move fast, think globally, and believe great teams are built by hiring exceptional people with conviction, curiosity, and the desire to make an impact.

With 20 offices across six continents and London as our HQ, we’re shaping the future of fintech – and we’re just getting started.

Role overview | Context

As Checkout.com continues to rapidly scale and evolve its international footprint, we are seeking an exceptionally strategic Head of Reward to champion our global total rewards philosophy. Following a significant transformation period within our People team—where we have leveled up our leadership, global equity schemes, operational reporting, and data capabilities—this role is a critical hire designed to transition our reward infrastructure from foundational stability to a high-yield competitive advantage.

Positioned as a key strategic partner to our leadership team, the incoming leader will directly shape a performance-led culture by aligning our total rewards with commercial growth, ensuring we continue to attract and retain world-class talent across the fintech ecosystem.

Role overview | Remit and Responsibilities

We are looking for a seasoned, highly strategic leader with deep domain expertise who can act as an organizational challenger and a trusted partner to senior leadership. Operating with a high degree of emotional intelligence, you will act as a "disruptor" within the people ecosystem, comfortable creating constructive conflict and relentlessly raising the global performance bar alongside the Executive Team. This role demands a leader who steps away from the "ivory tower" to actively collaborate on the ground, driving true organizational adoption of performance and compensation frameworks across all business lines.

• Global Reward Strategy & Execution: Design, implement, and optimize a comprehensive global reward strategy incorporating base pay, variable compensation, and benefits that are dynamically fit for purpose across every international location.

• Equity Architecture & Management: Take complete ownership of our global equity strategy, managing the long-term migration away from legacy option models and ledger systems toward a scalable framework that aligns directly with the CHRO and Founder-CEO.

• Driving a High-Performance Culture: Partner with E-team members to design and aggressively enforce strict performance-driven compensation programs, ensuring people managers globally adopt and execute our unified talent calibration and probation bars.

• Data-Driven Decision Making & Insights: Conduct sophisticated market benchmarking and peer analysis within the payments and technology sectors, effectively playing back competitive trends, analytics, and actionable metrics to the CHRO and Founder-CEO.

• Stakeholder & Founder Alignment: Build deep, high-trust advisory relationships with our Founder-CEO and Executive Team, confidently navigating a fast-moving environment where creative, innovative proposals must balance alongside the strong strategic vision of the primary shareholder.

• Operational Excellence & Parity: Oversee complex global benefits programs to ensure systemic pay equity, consistency, and structural alignment, providing "flexibility within a framework" to capture critical local nuances.

• Hands-on Relationship Building: Devote significant energy to working cross-functionally across our regional offices, building deep partnerships with internal teams rather than directing strategy abstractly.

• Team Leadership: Lead, inspire, and grow a high-performing team of reward and compensation professionals, instilling a culture of continuous development, technical accuracy, and strategic impact.

Role overview | Desired Background, Core Competencies

The ideal candidate for the role will bring:

• Extensive Domain Leadership: A proven track record of successfully leading global compensation, benefits, and total rewards strategies in fast-paced, high-growth matrixed tech environments.

• FinTech or High-Growth Scale Experience: Deep experience operating within target sectors including Payments, FinTech, e-commerce, consumer tech, or enterprise software; explicitly holding a strong bias toward private/scale-up environments over rigid public corporate systems.

• Subject Matter Expertise in Equity: Exceptional technical command over complex equity programs, option structuring, and cap table models—proven ability to strategically navigate evolution in a company's financial valuation structure is paramount.

• Founder-Led Navigation: Demonstrated success operating inside a high-growth, founder-led organization, showcasing the dexterity to pitch bold, creative ideas while fully respecting and executing the final directional decisions of the CEO.

• High EQ & Challenger Mentality: An intentional balance of high emotional intelligence with a robust "challenger" mindset; someone who thrives when driving a relentless performance culture, navigating healthy friction, and holding managers accountable.

• Execution over Design: A track record of not just designing pristine frameworks, but successfully driving enterprise-wide adoption, organizational turnaround, and measurable cultural alignment.

• Analytical Rigor: Strong capability in leveraging People Analytics and insights to influence strategic business narratives, though happy to compromise slightly on advanced analytics if core reward and equity spikes are extraordinarily strong.

Additional Information

Bring all of you to work

We create the conditions for high performers to thrive, through real ownership, fewer blockers, and work that makes a difference from day one.

Here, you’ll move fast, take on meaningful challenges, and be recognized for the impact you deliver. It’s a place where ambition gets met with opportunity, and where your growth is in your hands.

We work as one team, and we back each other to succeed. So whatever your background or identity, if you’re ready to grow and make a difference, you’ll be right at home here.

It’s important we set you up for success and make our process as accessible as possible. So let us know in your application, or tell your recruiter directly, if you need anything to make your experience or working environment more comfortable.

Life at Checkout.com

We understand that work is just one part of your life. Our hybrid working model offers flexibility, with three days per week in the office to support collaboration and connection.

Curious about what it’s like to be part of our team? Visit our Careers Page to learn more about our culture, open roles, and what drives us.

For a closer look at daily life at Checkout.com, follow us on LinkedIn and Instagram