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Checkout.com is seeking a Senior Director of Total Rewards & Performance to lead a strategic transformation of the company's global compensation, benefits, and equity infrastructure. The role sits at the executive level, reporting to the CHRO and partnering directly with the Founder-CEO and leadership team.
Key responsibilities include designing and executing a comprehensive global reward strategy across base pay, variable compensation, and benefits tailored to 20+ international locations. You will own the complete equity architecture, managing migration from legacy option models to a scalable framework aligned with company valuation and founder vision. A critical mandate is driving a high-performance culture by partnering with the executive team to design and enforce strict performance-driven compensation programs, ensuring global adoption of unified talent calibration and probation standards.
You will conduct sophisticated market benchmarking within payments and fintech sectors, translating competitive trends and analytics into actionable insights for senior leadership. The role demands hands-on cross-functional collaboration across regional offices, building deep partnerships rather than directing abstractly. You will oversee complex global benefits programs to ensure pay equity, consistency, and structural alignment while capturing local nuances. You will lead and develop a high-performing team of reward and compensation professionals.
The ideal candidate brings extensive experience leading global compensation and total rewards strategies in fast-paced, high-growth, matrixed tech environments—particularly fintech, payments, e-commerce, or enterprise software. You need exceptional technical expertise in complex equity programs, option structuring, and cap table models. Demonstrated success operating within founder-led, high-growth organizations is essential, with proven ability to pitch bold ideas while respecting and executing CEO direction. You combine high emotional intelligence with a challenger mentality, thriving when driving performance culture and holding managers accountable. Above all, you have a track record of execution and enterprise-wide adoption, not just pristine framework design.
