Head of Total Rewards

Handshake is the career network for the AI economy. 20 million knowledge workers, 1,600 educational institutions, 1 million employers (including 100% of the Fortune 50), and every foundational AI lab trust Handshake to power career discovery, hiring, and upskilling, from freelance AI training gigs to first internships to full-time careers and beyond. This unique value is leading to unparalleled growth; in 2025, we tripled our ARR at scale.

Why join Handshake now:

• Shape how every career evolves in the AI economy, at global scale, with impact your friends, family and peers can see and feel

• Work hand-in-hand with world-class AI labs, Fortune 500 partners and the world’s top educational institutions

• Join a team with leadership from Scale AI, Meta, xAI, Notion, Coinbase, and Palantir, among others

• Build a massive, fast-growing business with billions in revenue

As the Head of Total Rewards at Handshake, you will lead the strategy and execution of our global compensation and benefits programs during a period of hyper-growth. This role requires both strategic vision and operational rigor. You will bring clarity and structure to a fast-evolving organization, ensuring our compensation and benefits programs scale thoughtfully with the business.

• Lead the strategy and execution of total rewards programs, spanning base compensation, equity, incentives, and benefits, aligned to business priorities and long-term value creation.

• Design scalable total rewards structures that attract and retain top talent while balancing affordability, equity burn, and cash discipline.

• Bring strong and meticulous program management to total rewards, ensuring key initiatives and targeted solutions are clearly documented, tracked, and delivered with precision.

• Partner closely with executive, business, and hiring leaders to provide high-context guidance on offers, promotions, retention, and org changes.

• Build and evolve incentive programs that align individual and team outcomes with company performance, with clear mechanics and strong adoption across leaders.

• Own benefits strategy and vendor partnerships across health, wellness, leave, and retirement, ensuring programs are competitive and experience-forward.

• Build and scale a high-performing total rewards function by leveraging the team and the right tools, systems, and partners to expand impact.

• 8+ years of experience in total rewards analysis and strategy, with a focus on hyper-growth, VC-backed, pre-IPO companies.

• Proven track record of developing compensation frameworks in dynamic environments.

• Deep expertise in equity compensation

• Expertise in using compensation survey tools like Pave and Radford for data-driven decision making.

• Strong analytical skills, with experience in data audits and variance analysis.

• Exceptional communication and presentation skills, with the ability to influence senior stakeholders.

• Deep knowledge of compliance standards, including FLSA and pay equity laws.

• Experience in leading compensation strategies through IPO

• Familiarity with HR systems such as Workday and Ashby.

• Previous experience in high-growth tech companies.

Handshake delivers benefits that help you feel supported—and thrive at work and in life.

The below benefits are for full-time US employees.

🎯 Ownership: Equity in a fast-growing company

💰 Financial Wellness: 401(k) match, competitive compensation, financial coaching

🍼 Family Support: Paid parental leave, fertility benefits, parental coaching

💝 Wellbeing: Medical, dental, and vision, mental health support, $500 wellness stipend

📚 Growth: $2,000 learning stipend, ongoing development

💻 Remote & Office: Internet, commuting, and free lunch/gym in our SF office

🏝 Time Off: Flexible PTO, 15 holidays + 2 flex days

🤝 Connection: Team outings & referral bonuses

Explore our mission, values, and comprehensive US benefits at joinhandshake.com/careers.