Director of Benefits

Robinhood • Chicago, NY

1d • Onsite

About The Position

Robinhood is seeking a Director of Benefits to lead the strategy, design, and delivery of benefit programs for its global workforce. This role involves defining the benefits philosophy from first principles, creating programs that attract and retain talent, reinforce a high-performance culture, and deliver an outstanding employee experience. The Director will manage a team, oversee vendor relationships, collaborate with Legal and Finance, and handle aspects from annual renewals to M&A due diligence. This is a high-visibility role based in Chicago, IL, Menlo Park, CA, and New York, NY offices, with a requirement for in-person attendance five days per week. Robinhood emphasizes the value of in-person work for progress, innovation, and community building, with an intentional and energizing office experience designed to support high-performing teams.

Requirements

• 10+ years of experience in benefits, with a track record of designing and implementing global programs
• Deep expertise across health, welfare, retirement, and leave – both US and international
• A first-principles approach to designing programs, processes, and policies
• Strong analytical skills and comfort modeling program costs, utilization, and ROI
• Strong fluency with AI tools, with curiosity to experiment, learn, and incorporate new tools and techniques
• M&A experience including benefits due diligence and integration
• Solid understanding of regulatory and compliance requirements across global jurisdictions
• A track record of driving process improvement and automation without sacrificing the employee experience
• Exceptional verbal and written communication skills, and ability to present complex topics clearly to employees and leadership

Responsibilities

• Define and evolve Robinhood's global benefits philosophy and strategy, starting from first principles
• Design, implement, and manage programs across health, welfare, retirement, leave, and voluntary benefits for a global workforce
• Evaluate, streamline, and automate benefits processes with a constant focus on employee experience
• Lead annual program reviews and renewals, including vendor negotiations
• Monitor market practices and the regulatory landscape to keep our programs competitive and compliant across all jurisdictions
• Partner with Legal and Finance on compliance and regulatory obligations across regions
• Lead benefits due diligence and integration for M&A activity
• Build, develop, and lead a high-performing benefits team

Benefits

• Performance-driven compensation with multipliers for outsized impact
• Bonus programs
• Equity ownership
• 401(k) matching
• 100% paid health insurance for employees with 90% coverage for dependents
• Lifestyle wallet — a highly flexible benefits spending account for wellness, learning, and more
• Employer-paid life & disability insurance
• Fertility benefits
• Mental health benefits
• Company holidays
• Paid time off
• Sick time
• Parental leave
• Exceptional office experience with catered meals, events, and comfortable workspaces

What This Job Offers

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