There are NO limits to your career: come shape the future and be part of a truly unique global culture at OutSystems!
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.
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).
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.).
Salary Determination: Our salary range is based on industry standards, company performance, and market conditions. We offer competitive compensation packages to attract and retain top talent. In determining salary ranges, we consider factors such as
- Market Research: Industry reports, salary surveys, and online salary databases
- Company Performance: Financial performance, revenue growth, and budget allocation
- Job Requirements: Skills, experience, and qualifications necessary for the role
- Geographic Location: Cost of living, market conditions, and industry standards in our region
- $240,000 - $285,000 Base Salary
OutSystems is a leading AI Development Platform built for the enterprise. Global organizations trust OutSystems to rapidly build mission-critical apps and agents, modernize legacy processes with agentic systems, and govern their entire AI portfolio across complex regulatory environments, all on one unified platform.
As the future becomes agentic, our customers need us now more than ever. While AI has opened the door to extraordinary possibilities, most large organizations find themselves stuck on one side of the "enterprise gap" because AI by itself doesn't solve their complex use cases and business challenges. OutSystems bridges the "enterprise gap" by combining the speed of generative AI with a deterministic, enterprise-grade framework. We provide the tools for teams of any size to deliver high-quality, reliable AI solutions that drive real business impact.
We are looking for passionate, talented, and motivated people to join us as we empower organizations to build, deploy, and scale the next generation of enterprise software. While we are leading the charge into the agentic era, our mission is broader: we are the platform enterprise leaders trust to evolve their entire business, accelerating innovation through secure, governed human-AI collaboration.
OutSystems is a global company, with more than 900k developer community members, 1,700 employees, more than 600 partners, and thousands of active customers in over 75 countries and across 21 industries. Founded in 2001, OutSystems now has offices in the United States, United Kingdom, the Netherlands, Portugal, Germany, the UAE, Japan, Hong Kong, Malaysia, Australia, India, and Singapore, and includes a thriving, worldwide community of remote employees.
Our customers are some of the world's most recognizable brands across diverse industries— such as Toyota, Heineken, Bosch, KeyBank, and UCLA—who trust OutSystems to deliver ROI and transformational impact.
Consistently recognized as a leader by top analyst firms Gartner, IDC and Forrester, OutSystems continues to shape the future of enterprise software development in the agentic era. We are proud to be named a leader in more than 100 categories on G2, including #1 in Customer Satisfaction in Enterprise Low Code Development, and most recently as a leader in AI Agent Building in the G2 Spring 2026 Reports.
Working at OutSystemsOur culture is built on our core values of Trust, Customer Success, Innovation, and Alignment. We operate as one global OutSystems team, taking ownership to pursue our vision of being the AI platform enterprise leaders trust to build, secure, and evolve their most critical applications and systems.
What do we have to offer you?
A company at the vanguard of the agentic revolution, where we don’t just react to AI innovation—we architect it. Joining OutSystems means stepping onto a high-growth rocket ship that combines the fearless agility of a startup with the sophisticated, global foundation of an enterprise powerhouse.
Real growth opportunities. We don't just talk about development; we invest in it through structured programs designed to scale your expertise. Whether you are aiming for vertical progression, exploring lateral moves into new domains, or mastering specialized AI skills through our Professional Development Fund and Internal Mobility Program, we provide the resources to get you there.
A global collective of world-class talent, where you’ll collaborate with enterprise software legends and sought-after thought leaders. At OutSystems, our industry experts aren't just visionaries—they are accessible, approachable mentors who are deeply invested in your growth as we architect the agentic future together.
OutSystems nurtures an inclusive culture where talented individuals from all backgrounds are empowered to learn, experiment and make an impact. . We believe that driving our next phase of growth requires the radical creativity that only comes from diverse perspectives. We are committed to building a team as global and diverse as the organizations we serve, ensuring every individual can perform to their full potential. As an equal opportunity employer, all qualified applicants receive equal consideration regardless of race, origin, religion, sex, sexual orientation, gender identity, disability, veteran status, or any other protected status.
OutSystems Boston, Massachusetts, USA Office
55 Thomson Pl , 2nd floor, Boston, MA, United States, 02210
Similar Jobs
What you need to know about the Boston Tech Scene
Key Facts About Boston Tech
- Number of Tech Workers: 269,000; 9.4% of overall workforce (2024 CompTIA survey)
- Major Tech Employers: Thermo Fisher Scientific, Toast, Klaviyo, HubSpot, DraftKings
- Key Industries: Artificial intelligence, biotechnology, robotics, software, aerospace
- Funding Landscape: $15.7 billion in venture capital funding in 2024 (Pitchbook)
- Notable Investors: Summit Partners, Volition Capital, Bain Capital Ventures, MassVentures, Highland Capital Partners
- Research Centers and Universities: MIT, Harvard University, Boston College, Tufts University, Boston University, Northeastern University, Smithsonian Astrophysical Observatory, National Bureau of Economic Research, Broad Institute, Lowell Center for Space Science & Technology, National Emerging Infectious Diseases Laboratories
