Global Benefits Director: Strategy, Compliance & Impact

Rainfall Ventures; Illinois; On-site; USD 198,000 - 233,000; Full time

Benefits offered by this job

Bonus opportunities

Equity ownership

401(k) matching

Best-in-class benefits

Job summary

Robinhood is seeking a Director of Benefits to own the strategy, design, and delivery of global benefits programs. You will define our philosophy from first principles to attract and retain top talent, influence vendor and regulatory decisions, and partner with Legal and Finance on renewals and due diligence.

This high-visibility role shapes employee experience across regions. The role requires building and leading a high-performing benefits team, with in-person collaboration across Chicago, IL;

Qualifications

• 10+ years of benefits experience with global programs.
• Deep expertise across health, welfare, retirement, and leave – US and international.
• First-principles approach to program design.
• Strong analytical skills for costs, utilization, and ROI.
• Fluency with AI tools and curiosity to adopt new tech.
• M&A due diligence and integration experience.
• Strong regulatory/compliance knowledge across jurisdictions.
• Drive process improvements and automation while preserving employee experience.
• Excellent verbal and written communication.

Responsibilities

• Define and evolve the global benefits philosophy and strategy.
• Design, implement, and manage health, welfare, retirement, leave, and voluntary benefits globally.
• Streamline benefits processes with a focus on employee experience.
• Lead annual program reviews and vendor negotiations.
• Monitor regulatory landscape to stay compliant across regions.
• Collaborate with Legal and Finance on compliance and obligations.
• Lead benefits due diligence and integration for M&A activity.
• Build, develop, and lead a high-performing benefits team.

Skills

Global benefits design

Vendor management

Regulatory compliance

M&A due diligence

Cost/ROI modeling

AI tools fluency

Process automation

Executive communication

Leadership

Tools

AI tools

Job description

Robinhood is seeking a Director of Benefits to own the strategy, design, and delivery of global benefits programs. You will define our philosophy from first principles to attract and retain top talent, influence vendor and regulatory decisions, and partner with Legal and Finance on renewals and due diligence.

This high-visibility role shapes employee experience across regions. The role requires building and leading a high-performing benefits team, with in-person collaboration across Chicago, IL;