Head of Total Rewards

Handshake • San Francisco, CA

3d

About The Position

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.

Requirements

• 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.

Nice To Haves

• Experience in leading compensation strategies through IPO
• Familiarity with HR systems such as Workday and Ashby.
• Previous experience in high-growth tech companies.

Responsibilities

• 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.

Benefits

• 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

What This Job Offers

• Job Type: Full-time
• Career Level: Executive
• Education Level: No Education Listed