Benefits Manager

Dandy is transforming the massive and antiquated dental industry—an industry worth over $200B. Backed by some of the world’s leading venture capital firms, we’re on an ambitious mission to simplify and modernize every function of the dental practice through technology. As we expand our reach globally, Dandy is building the operating system for dental offices around the world—empowering clinicians and their teams with technology, innovation, and world-class support to achieve more for their practices, their people, and their patients.

About the Role

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.

What You'll Do

• 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.

What We're Looking For

• 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.

Bonus Points For

• 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.

Req ID: J-971

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.

Dandy is proud to be an equal-opportunity employer. We are committed to building a diverse and inclusive culture that celebrates authenticity to win as one. We do not discriminate on the basis of race, religion, color, national origin, gender, gender identity, sexual orientation, age, marital status, disability, protected veteran status, citizenship or immigration status, or any other legally protected characteristics.

Dandy also fully complies with the Americans with Disabilities Act (ADA). We are dedicated to embracing challenges and creating an accessible, inclusive workplace for all individuals. If you require any accommodations for your interview or have any questions beforehand, rest assured that we will do everything we can to meet your needs. Visit Dandy Careers for more!

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