Manager of Payroll and Benefits

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 Manager of Payroll & Benefits to serve as our in-house payroll subject matter expert (SME) and own the strategy and execution of our U.S. payroll and benefits programs. This is a critical role within the People Operations team, responsible for delivering compliant, accurate, and employee-friendly payroll and benefits experiences at scale.

In the immediate term, you’ll lead all aspects of domestic payroll operations—owning systems, compliance, and process optimization—while managing U.S. employee benefits administration and strategy. As Dandy continues to expand globally, the scope of this role will grow to include ownership of international payroll and benefits—giving you the opportunity to build scalable, compliant, and locally relevant programs in new markets.

This is an ideal opportunity for a seasoned payroll professional who thrives on ownership, precision, and continuous improvement, and is ready to take on a global mandate as part of a high-growth team.

What You'll Do

• Own U.S. payroll strategy and compliance, overseeing accurate and timely processing while managing a direct report responsible for day-to-day execution.

• Act as Dandy’s payroll SME, with full fluency in systems, processes, and regulations—able to step in directly when needed and guide decision-making at all levels.

• Develop and document standard operating procedures to drive payroll accuracy, transparency, and business continuity.

• Administer and evolve U.S. benefits programs—including health, retirement, and wellness—owning vendor relationships, open enrollment, and long-term strategy.

• Lead the build and launch of international payroll and benefits programs in new markets (e.g., Brazil, U.K., Canada), including vendor selection, systems setup, and compliance.

• Lead cross-functional partnership with Legal, Finance, and HR to ensure alignment, data accuracy, and compliance across payroll and benefits.

• Serve as the escalation point for complex payroll and benefits issues, ensuring a seamless and high-quality employee experience.

What We're Looking For

• 6+ years of full-cycle U.S. payroll experience, including multi-state complexity, systems ownership, and compliance leadership.

• Proven track record acting as a payroll SME within an organization—advising leadership and resolving complex issues.

• Experience with payroll platforms such as Paylocity, ADP, or UKG; strong systems fluency and problem-solving skills.

• 2+ years of experience managing employee benefits programs, including vendor/broker management and open enrollment.

• Knowledge of payroll and benefits compliance requirements (e.g., IRS, DOL, ERISA, ACA, COBRA).

• Demonstrated success building scalable payroll processes, documentation, and internal controls.

• Ability to quickly learn and own complex systems and regulations, with a strong eye for detail and accuracy.

• Excellent communication and project management skills with the ability to distill and explain complex topics to a range of stakeholders.

• A process and solutions-oriented mindset, with a bias for ownership and execution.

• Eagerness to take on international scope and grow with the company as our footprint expands.

Bonus Points For

• Prior experience administering payroll through UKG.

• Experience launching international payroll and benefits in markets like Canada, the U.K., or Latin America.

• Familiarity with global payroll vendors and compliance requirements.

• Prior experience supporting HR/Finance operations during international expansion.

• Certified Payroll Professional (CPP) or CEBS (Certified Employee Benefit Specialist).

• Experience administering equity compensation through payroll and benefits lenses.

The reasonably estimated salary for this role at Dandy is $126,550 - $149,000 plus equity. Actual compensation is based on a number of factors including, but not limited to the candidate's skills, qualifications, and experience.

Req ID: J-573

For full-time