Benefits Manager

Dandy

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About The Position

Dandy is hiring a Benefits Manager to own the strategy and execution of our U.S. employee benefits programs and play a critical role in building our newly formed Total Rewards function. This is a critical role within the People Operations organization, responsible for delivering compliant, competitive, and employee-friendly benefits experiences at scale.
In the immediate term, you’ll lead all aspects of U.S. benefits administration and strategy, including health and welfare programs, retirement plans, time off programs and wellness offerings. You’ll own vendor relationships, open enrollment, benefits compliance, and the continuous evolution of our benefits suite. A key near-term focus will be scoping Dandy’s long-term domestic benefits strategy, including evaluating our 2027 renewal approach and potential transition from a fully insured model to a self-funded structure.
As Dandy continues to expand globally, this role will be instrumental in designing and launching benefits programs in new international markets, partnering closely with Deel, our Employer of Record (EOR), to ensure compliant, competitive, and locally relevant offerings.
This is an ideal opportunity for a seasoned benefits leader who thrives on ownership, precision, and building scalable programs in a high-growth environment.

Requirements

• 6+ years of experience managing U.S. employee benefits programs, including health and welfare plans, retirement benefits, and vendor/broker relationships.
• Demonstrated experience launching and scaling international benefits programs in new markets, ideally in partnership with an EOR or global vendors.
• Strong benefits subject matter expertise, including compliance & audit related requirements (ERISA, ACA, COBRA, HIPAA, IRS regulations).
• Proven ownership of open enrollment cycles and ongoing benefits administration.
• Experience driving strategic benefits planning, including renewals, plan design, and cost modeling.
• Strong cross-functional partnership skills, particularly with Payroll, Finance and Accounting to ensure accurate benefits administration, financial forecasting and compliance.
• A detail-oriented, curious mindset with a high bar for execution and accountability.
• Excellent communication and project management skills, with the ability to clearly explain benefits concepts to diverse stakeholders.
• Passionate about building and scaling programs in a fast-growing environment.

Nice To Haves

• Experience evaluating or implementing self-funded health plans.
• Hands-on experience working with Employer of Record (EOR) partners such as Deel.
• Certified Employee Benefit Specialist (CEBS) or similar professional certification.
• Experience partnering closely with Compensation teams on Total Rewards strategy.
• Experience influencing senior leadership audiences
• Experience supporting high-growth or scaling organizations.

Responsibilities

• Own U.S. benefits strategy and administration across health, retirement, time off and wellness programs, ensuring competitive, compliant, and employee-centered offerings.
• Serve as Dandy’s benefits subject matter expert (SME), guiding leadership decisions and resolving complex benefits issues.
• Lead vendor and broker relationships, including renewals, plan design, performance management, and issue resolution.
• Own open enrollment end-to-end, from planning, communications and enablement to systems setup and post-enrollment audits.
• Drive Dandy’s domestic benefits strategy, including evaluating the 2027 renewal approach and fully insured versus self-funded models in partnership with Finance and brokers.
• Lead the design and launch of international benefits programs across new markets (U.K., Spain, France, Italy, Australia), working closely with Deel to ensure compliance and strong employee experiences.
• Own reporting and analytics associated with benefits programs to track utilization, measure success and guide future enhancements.
• Partner closely with Payroll and Accounting to ensure benefits policies, deductions, and financial decisions are accurately reflected in biweekly payroll cycles and compliant across systems.
• Continuously assess and improve benefits programs to align with market trends, business needs, local context and the overarching Total Rewards strategy.

Benefits

• For full-time positions, Dandy offers a wide range of best-in-class, comprehensive, and inclusive benefits tailored to each country where we operate.
• Our local benefits packages typically include healthcare, dental, mental health support, parental planning resources, retirement savings options, and generous paid time off—ensuring our team members are supported no matter where they live and work.

What This Job Offers

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