Director, Insurance Services

About OnPay

OnPay is a fast-growing software company headquartered in Atlanta, offering a modern cloud-based payroll, HR, and benefits solution for small to midsize businesses. We’re currently seeking talented and curious individuals to join our team. We want to hear from you if you are interested in joining an exciting and fast-growing company!

Learn more at OnPay.com

We’re on a mission to combine excellent customer service with payroll expertise and superb technology — and we are scaling fast as we’ve just raised $100 million in growth funding led by Carrick Capital Partners.

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. This is a brand-new position that will oversee all aspects of the benefits client experience, including developing robust processes, setting objectives, and creating initiatives. In addition, this role will support and promote excellent client satisfaction.

What You’ll Do

• 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

What You Bring

• 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
  

Why OnPay?

• 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.

Location & Compensation

Remote (U.S.) | Atlanta HQ Optional

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.

Recruiting Fraud Alert:

To all candidates: your personal information and online safety are top of mind for us. At OnPay, recruiters only direct candidates to apply through our official career page at careers.onpay.com

Recruiters will never request payments or ask for financial account information or sensitive information like social security numbers. If you are unsure if a message is from OnPay, please email careers@onpay.com

EEO Statement

OnPay is proud to be an equal opportunity workplace dedicated to pursuing and hiring a diverse workforce. We want candidates from multiple backgrounds and lifestyles to create a broader set of perspectives. We make all employment decisions without regard to gender, sexual orientation, gender identity, race, color, religion, age, pregnancy, national origin, veteran status, disability, or any other classification protected by applicable laws.