Global Benefits Director: Strategy, Growth & Compliance

Confidential; Chicago, New York (IL, NY); On-site; USD 198,000 - 233,000; Full time

Benefits offered by this job

100% paid health insurance

Equity ownership

401(k) matching

Bonus programs

Lifestyle wallet

Job summary

United States Digital Space LLC is seeking a Director of Benefits to own the strategy, design, and delivery of global benefit programs. You will define philosophy, lead a team, manage vendor relationships, and partner with Legal and Finance to maintain compliant, high-impact programs across multiple jurisdictions.

Based in Chicago with in-person attendance expected, the role emphasizes first-principles design, cost modeling, and a strong focus on employee experience, equity, and growth within a

Qualifications

• 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
• 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 the company'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

Skills

Benefits strategy

Global programs

Vendor negotiations

Regulatory compliance

People leadership

Data analytics

ROI modeling

AI tools

M&A due diligence

Job description

United States Digital Space LLC is seeking a Director of Benefits to own the strategy, design, and delivery of global benefit programs. You will define philosophy, lead a team, manage vendor relationships, and partner with Legal and Finance to maintain compliant, high-impact programs across multiple jurisdictions.

Based in Chicago with in-person attendance expected, the role emphasizes first-principles design, cost modeling, and a strong focus on employee experience, equity, and growth within a