Senior Director, Global Total Rewards

Role Description

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.

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.

Global Compensation & Equity Strategy

• Total Rewards Architecture: Lead the strategic design, philosophy, and evolution of all core global compensation programs, ensuring a tight link between performance, retention, and business objectives.
• Equity Programs: 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.
• Annual Cycles & Governance: 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.

Global Benefits Strategy & Management

• Benefits Strategy: 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.
• Vendor & Broker Relations: Oversee relationships with global and regional benefits brokers, insurance carriers, and third-party administrators to optimize cost-efficiency, service levels, and program competitiveness.
• Wellness Initiatives: Champion global health and wellness initiatives that support employee well-being and align with the OutSystems culture of holistic employee care.

Compliance, Analytics & Cross-Functional Leadership

• Regional & Legal Compliance: 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.
• Executive Modeling & Insights: 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.
• Stakeholder Collaboration: 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.
• Process Modernization: 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.

Qualifications

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

Skills & Competencies

• Technical Analytics: Exceptional analytical capabilities with advanced data modeling experience and mastery of modern enterprise data ecosystems.
• Systems Expertise: Hands-on experience with modern compensation and HR systems (e.g., Workday Compensation, Radford, Pave, and sophisticated market-pricing tools).
• Leadership & Influence: Proven track record of navigating complex cross-functional relationships, influencing C-suite stakeholders (including the CPO), and managing multi-million dollar global budgets.
• Execution & Detail: Project management skills with high attention to detail and an unwavering ability to navigate competing, high-stakes global deadlines simultaneously.
• Digital Literacy: Advanced proficiency across Google Suite and AI technologies (Claude/Gemini/NotebookLM etc.).

Benefits

• A company at the vanguard of the agentic revolution, where we don’t just react to AI innovation—we architect it.
• Real growth opportunities through structured programs designed to scale your expertise.
• A global collective of world-class talent, collaborating with enterprise software legends and sought-after thought leaders.
• An inclusive culture where talented individuals from all backgrounds are empowered to learn, experiment, and make an impact.