Director, Insurance Services

About the role

The Director of Insurance Services will build and lead a specialized team dedicated to employee benefits administration and support. This team will assist clients in navigating complex benefits situations and open enrollments, building and overseeing client accounts in the Benefits Administration system, providing ongoing support, communicating with insurance carriers, and maintaining consistent overall communication.

Responsibilities

• Set the overall vision and strategic plan for the Benefits Support Team, focusing on leading a seamless benefits experience and driving growth through process and retention improvements
• Develop robust, scalable processes and procedures to ensure timely, accurate responses to clients regarding benefits enrollment, payroll deductions, and policy changes
• Act as a liaison between the Benefits Support team, internal departments, and external insurance partners
• Ensure that messaging to clients regarding benefits, compliance, and features is consistent across the organization
• Develop SLAs for benefits-related inquiries to ensure excellent customer service during high-volume periods, such as Open Enrollment
• Drive successful customer outcomes, benefit product adoption, and achieve overall positive customer experiences
• Lead, motivate, and coach a team of Benefits Support Specialists
• Utilize key metrics related to benefits administration and support to continuously improve strategies and initiatives
• Perform other duties as assigned

Requirements

• 6–10+ years of experience in the SMB market, account management, and/or consulting required
• 5+ years of benefits brokerage experience required
• Proven leadership in building and scaling teams for growth, managing high-value portfolios, and driving retention required
• Experience with Benefits Administration systems strongly preferred
• Bachelor's degree preferred

Benefits

• Momentum that matters: We’re backed by over $100MM in new funding and scaling rapidly.
• Market-leading product: OnPay consistently ranks among the highest-rated payroll solutions, earning top marks for usability, customer satisfaction, and support.
• Remote flexibility: Work from anywhere in the U.S., or join our collaborative HQ team in Atlanta’s Ponce City Market if you reside in the Atlanta metro area.
• Competitive compensation: Base salary + variable compensation + stock options = real upside for high performers.
• Comprehensive benefits: 4 weeks PTO + paid holidays, Medical/Dental/Vision, Short- & Long-Term Disability, Life Insurance, Fertility Benefits, Parental Leave, and a 401(k) with company match.
• Growth culture: Join a team with deep payroll expertise, modern SaaS momentum, and a genuine commitment to helping employees grow their careers.
• Client-first ethos: OnPay is built on a culture of transparency and service — from our transparent pricing to our commitment to making small business simpler.

Pay

The compensation range for the role is up to $200k OTE. Final offer amounts are determined by multiple factors, including candidate experience and expertise, and may vary from the amounts listed above.