Director of Benefits

Robinhood; Chicago (IL); On-site; USD 198,000 - 233,000; Full time

Benefits offered by this job

100% paid health insurance

401(k) matching

Fertility benefits

Mental health benefits

Life & disability insurance

Catered meals

Job summary

Robinhood is seeking a senior leader to own our global benefits function, shaping programs across health, welfare, retirement, and leave for a diverse workforce. You will drive cost modeling, regulatory alignment, and strategic vendor relationships while growing a high-performing team.

The role balances strong analytical rigor with a focus on employee experience and innovative, AI-enabled tooling. This is a leadership role with significant impact on people programs.

Qualifications

• 10+ years of experience with global benefits programs
• Deep expertise across health, welfare, retirement, and leave (US and international)
• First-principles approach to program design and policy
• Strong cost, utilization, and ROI modeling skills
• Fluency with AI tools and willingness to experiment
• M&A due diligence and integration experience
• Regulatory/compliance knowledge across jurisdictions
• Process improvement and automation without compromising employee experience
• Excellent verbal and written communication skills

Responsibilities

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

Skills

Global benefits design

Analytical skills

AI tools fluency

Communication skills

Job description

Join us in building the future of finance.

Our mission is to democratize finance for all. An estimated $124 trillion of assets will be inherited by younger generations in the next two decades. The largest transfer of wealth in human history. If you’re ready to be at the epicenter of this historic cultural and financial shift, keep reading.

About the team + role

We are building an elite team, applying frontier technologies to the world’s biggest financial problems. We’re looking for bold thinkers. Sharp problem-solvers. Builders who are wired to make an impact. Robinhood isn’t a place for complacency, it’s where ambitious people do the best work of their careers. We’re a high-performing, fast-moving team with ethics at the center of everything we do. Expectations are high, and so are the rewards.

The People team's mission is to build the systems, programs, and culture that enable Robinhood's employees to do the best work of their careers. We attract, develop, and retain exceptional talent — and design the programs that support people from their first day through every stage of their journey. We partner closely across the business to ensure our people strategy moves as fast as the company does. We're building something special, and we take that responsibility seriously.

What You’ll Do

• 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

What You Bring

• 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

Leadership expectations

• Drive high performance by setting clear, focused goals, giving real-time feedback, stretching top talent, and scaling impact through focus, innovation, and tech.
• Hire and retain top talent by setting a high bar, hiring only those who raise it, investing in onboarding, and addressing talent issues quickly and fairly.
• Create community by connecting work to purpose, removing friction while prioritizing safety, building trust and inclusion, and leading from the front with integrity.

What We Offer

• Challenging, high‑impact work to grow your career.
• Performance-driven compensation with multipliers for outsized impact, bonus programs, equity ownership, and 401(k) matching.
• Best-in‑class benefits to fuel your work, including 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, and mental health benefits.
• Time off to recharge including company holidays, paid time off, sick time, parental leave, and more!
• Exceptional office experience with catered meals, events, and comfortable workspaces.

In addition to the base pay range listed below, this role is also eligible for bonus opportunities + equity + benefits

Base pay for the successful applicant will depend on a variety of job‑related factors, which may include education, training, experience, location, business needs, or market demands. The expected base pay range for this role is based on the location where the work will be performed and is aligned to one of 3 compensation zones. For other locations not listed, compensation can be discussed with your recruiter during the interview process.

Base Pay Range

Zone 1 (Menlo Park, CA; New York, NY; Bellevue, WA; Washington, DC)

$225,000—$265,000 USD

Zone 2 (Denver, CO; Westlake, TX; Chicago, IL)

$198,000—$233,000 USD

Zone 3 (Lake Mary, FL; Clearwater, FL; Gainesville, FL)

$176,000—$207,000 USD

This role is based in our Chicago, IL, Menlo Park, CA, and New York, NY offices, with in‑person attendance expected 5 days per week.

At Robinhood, we believe in the power of in‑person work to accelerate progress, spark innovation, and strengthen community. Our office experience is intentional, energizing, and designed to fully support high‑performing teams.

If our mission energizes you and you’re ready to build the future of finance, we look forward to seeing your application.

AI Usage Disclosure

Robinhood uses artificial intelligence (AI) tools to support parts of our recruiting process. These tools enhance the efficiency and consistency of our hiring process; however, all hiring decisions are made by our hiring teams.

Robinhood provides equal opportunity for all applicants, offers reasonable accommodations upon request, and complies with applicable equal employment and privacy laws. Inclusion is built into how we hire and work—welcoming different backgrounds, perspectives, and experiences so everyone can do their best. Please review the Privacy Policy for your country of application.