Jobs · Human Resources · Massachusetts

Senior Director, Global Total Rewards

OutSystems · Boston, MA · Today
Human ResourcesFull-time

About the role

We are 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 at OutSystems. Reporting directly to the Chief People Officer (CPO), this key leadership role is responsible for the overarching design, management, transformation, and execution of all global total rewards programs.

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.

Requirements

  • Experience: 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.

  • Education: Bachelor's degree in Business, Human Resources, Finance, or a related field (Master's or professional certifications like CCP or CEBS preferred).

  • Skills & Competencies: 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.).

Qualifications

  • Proven track record of success in a similar role.

  • Strong understanding of global labor markets and regulations.

  • Excellent communication and interpersonal skills.

  • Ability to work effectively in a fast-paced, dynamic environment.

  • Passion for technology and its impact on business.

Benefits

Join a company at the vanguard of the agentic revolution, where we don’t just react to AI innovation—we architect it. Real growth opportunities, a global collective of world-class talent, and a commitment to diversity and inclusion are just a few of the benefits you'll enjoy as part of the OutSystems team.

Pay

Competitive salary and benefits package.

Schedule

Full-time position.

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