Senior Director, Global Total Rewards

OutSystems•Boston, MA

21h•Remote

About The Position

OutSystems is seeking a visionary, highly motivated, and strategically minded Senior Director, Total Rewards to serve as the global subject matter expert and leader of our compensation, equity, and benefits strategy. This key leadership role is responsible for the overarching design, management, transformation, and execution of all global total rewards programs. The Senior Director will ensure our programs are highly competitive, compliant, and seamlessly aligned with our aggressive global business strategy across all regions, balancing sophisticated equity structures with modern global benefits programs.

Requirements

10–12+ years of progressive, deep total rewards experience, with a heavy emphasis on global equity structures, executive compensation, and managing global benefit plans within a high-growth, global enterprise.
Exceptional analytical capabilities with advanced data modeling experience and mastery of modern enterprise data ecosystems.
Hands-on experience with modern compensation and HR systems (e.g., Workday Compensation, Radford, Pave, and sophisticated market-pricing tools).
Proven track record of navigating complex cross-functional relationships, influencing C-suite stakeholders (including the CPO), and managing multi-million dollar global budgets.
Project management skills with high attention to detail and an unwavering ability to navigate competing, high-stakes global deadlines simultaneously.
Advanced proficiency across Google Suite and AI technologies (Claude/Gemini/NotebookLM etc.).

Nice To Haves

Master's or professional certifications like CCP or CEBS preferred.

Responsibilities

Lead the strategic design, philosophy, and evolution of all core global compensation programs, ensuring a tight link between performance, retention, and business objectives.
Serve as the principal architect for global equity refresh strategies, executive and non-executive bonus plans, and equity programs, keeping OutSystems competitive in the talent market.
Act as the executive global project owner for the annual compensation planning and annual refresh cycles. Direct the governance of timelines, executive communications, tool configurations, and seamless budget execution across all global business units.
Design, implement, and manage comprehensive global benefits programs (including health, wellness, retirement, and life insurance) that cater to a diverse, global workforce and drive high employee engagement.
Oversee relationships with global and regional benefits brokers, insurance carriers, and third-party administrators to optimize cost-efficiency, service levels, and program competitiveness.
Champion global health and wellness initiatives that support employee well-being and align with the OutSystems culture of holistic employee care.
Partner closely with regional HR and Total Rewards leaders (EMEA and APAC) to guarantee proactive global compliance with local pay equity laws, benefits mandates, and advanced corporate governance.
Conduct and oversee complex pay analysis, benefits utilization reviews, financial modeling, and predictive analytics to evaluate program effectiveness and deliver data-driven, board-ready recommendations to the CPO and executive leadership team.
Collaborate extensively with Finance, Executive Leadership, Talent Acquisition, People Operations, and HR Business Partners to ensure global programs are highly scalable, budget-aligned, and frictionlessly executed.
Champion the utilization of AI, advanced statistical analysis, data modeling, and modern compensation and benefits data tools to drive continuous process improvements and rigorous organizational reviews.