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Director of Benefits

Robinhood · Chicago, IL · Total Rewards

Posted Oct 2, 2026 · We last checked this listing on Oct 6, 2026

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Likely interview questions for this role

Written from this job description, not a generic list. Each one notes what the interviewer is really checking.

About your past

Tell me about a benefits program you redesigned. How did you measure whether it worked?

What they are checking: Whether they tie program changes to outcomes like use, satisfaction and cost.

Describe a time you communicated an unpopular benefits change to employees.

What they are checking: Whether they explain changes honestly and with care to keep trust.

How would you build and lead a benefits team that can keep up with company growth?

What they are checking: Whether they can develop people and scale processes, not just manage programs personally.

What would you do

Medical costs are rising 10 percent next year. What options would you bring to leadership?

What they are checking: Whether they can weigh plan design, funding and vendor options while protecting employees.

How would you support employees in other countries as the company expands globally?

What they are checking: Whether they understand local requirements and the challenge of keeping programs equitable.

About the work

How would you build a benefits strategy for a fast-growing company with a workforce that skews younger?

What they are checking: Whether they design around employee needs and life stages rather than copying a standard package.

How do you approach self-funded versus fully insured health plans?

What they are checking: Whether they understand the financial risk and control tradeoffs between funding models.

What compliance areas keep you up at night in benefits, like ERISA, ACA or nondiscrimination testing?

What they are checking: Whether they know the legal obligations that carry real penalties if missed.

How do you manage benefits brokers and vendors to get the best value?

What they are checking: Whether they hold partners accountable and run competitive reviews.

How do you use data to decide which benefits to add or cut?

What they are checking: Whether they use claims, utilization and survey data rather than trends or anecdotes.

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The full job description

As published by Robinhood.

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. As Director of Benefits, you'll own the strategy, design, and delivery of benefit programs that serve Robinhood's global workforce. You'll define our benefits philosophy from first principles — not defaulting to market convention, but building programs that genuinely help us attract and retain the best talent in the world, reinforce our high-performance culture, and deliver an outstanding employee experience. You'll lead a team, own key vendor relationships, partner with Legal and Finance, and bring your expertise to bear on everything from annual renewals to M&A due diligence. This is a high-visibility, high-impact role where you'll shape how thousands of employees experience Robinhood every day! 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.  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  Our ambitious roadmap requires a great culture shaped by exceptional leaders. Here’s what we expect from them: • 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 Click here to learn more about our Total Rewards, which vary by region and entity. 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.

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