Direct Bill Supervisor Jobs in Kentucky (NOW HIRING)

At We Insure Group, we are passionate, driven, and purposeful in our mission to personalize protection at the right value. We believe in delivering tailored insurance solutions that meet each client’s unique needs, ensuring they feel confident and supported in every decision.

As both a franchise platform and direct insurance provider, We Insure empowers like-minded entrepreneurs with the opportunity to own and operate successful agencies. With over 200 locations across 35 states, we support our agency owners, customers, and carrier partners by enabling faster service, greater efficiency, better choices, and improved results.

What sets us apart? We’re data-driven for better value and people led for better service. Our purpose is rooted in clarity, guidance, and long-term trust helping individuals and business owners make informed choices about their insurance coverage. We're building something meaningful and looking for purpose-driven individuals to help lead the way.

We Insure is seeking an experienced Premium Operations Manager to lead the day to day operations of our insurance commissions team. This role is responsible for ensuring the accurate and timely processing of insurance commissions while supporting Agency Bill, Direct Bill, carrier payments, and franchise owner inquiries across our growing franchise network.

You’ll lead a team responsible for commission operations and partner closely with franchise owners, insurance carriers, Carrier Relations, Technology, Accounting, and Operations to resolve issues, improve workflows, and deliver an exceptional franchise experience.

The ideal candidate has a strong understanding of insurance brokerage operations, commission processing, Agency Bill, Direct Bill, and franchise support, with a passion for leading teams, improving processes, and driving operational excellence.

• Manage the end to end insurance commission process, ensuring accurate and timely commission reconciliation, reporting, and payments for franchise owners, employees, and insurance carriers.
• Oversee day to day operational workflows, including commission reconciliations, Agency Bill, Direct Bill, trust accounting, cash and refund processing, carrier payments, and related operational activities.
• Manage and develop the commissions team by providing coaching, overseeing daily priorities, workload distribution, performance management, and professional development.
• Serve as a primary point of contact for franchise owners and insurance carriers, utilizing Atlassian Jira to manage support requests, resolve issues, and provide timely communication.
• Identify opportunities to optimize commission operations by establishing service level agreements (SLAs), improving workflows, reducing errors, enhancing operational efficiency, and delivering an exceptional franchise experience.
• Maintain and leverage Applied Epic and other insurance platforms to support commission processing, operational reporting, audits, and process improvements.
• Partner with Accounting during the month end close process by ensuring commission reconciliations, adjustments, journal entries, and reporting are completed accurately and on time.
• Collaborate cross functionally with Technology, Carrier Relations, Accounting, Legal, and Operations to resolve complex issues, implement system enhancements, automate workflows, and support operational excellence.
• Establish, monitor, and report on key operational KPIs and SLAs, including processing accuracy, payment cycle times, inquiry response times, backlog, and aging, while driving continuous improvement.
• Develop and maintain standard operating procedures (SOPs), operational documentation, and training materials to support a scalable and consistent operating model as We Insure continues to grow.

• 5+ years of experience in insurance brokerage operations, including insurance commissions, Agency Bill, Direct Bill, insurance accounting, or a related insurance operations function, with at least 2 years in a supervisory or management role.
• Strong leadership, problem solving, organizational, and communication skills.
• Ability to exercise sound judgment, adapt to changing priorities, and effectively manage competing demands in a fast paced environment.
• Demonstrated ability to implement change and drive continuous process improvement.
• Bachelor's degree in Accounting, Finance, Business, or a related field, or equivalent work experience.

• Insurance accounting or insurance commissions experience within an insurance brokerage environment.
• Experience with insurance and business systems, including one or more of the following: Applied Epic, AMS360, Workday, NetSuite, Atlassian Jira, Zendesk, or similar platforms.
• Proficiency in Microsoft Excel for data analysis, reporting, and operational performance.

• The work environment characteristics described here are representative of those an employee encounters while performing the essential functions of this job
• Reasonableaccommodations may be made to enable individuals with disabilities to perform the essential functions
• This position will be a hybrid office/remote work environment. All computer equipment necessary for the role will be providedto the employee
• This role requires 5% travel, Hybrid 3 days in office.The noise level is low to moderate depending on staff levels in the office and, when working remotely, noise level will be dependent on the employee’s chosen work location

• While performing the duties of this job, the employee is frequently required to stand; walk; talk and hear; sit for extended periods of time; use hands to finger, handle, or feel and reach with hands and arms
• The employee must occasionally lift and/or move up to 15 pounds
• Specific vision abilities required by the job include close vision, distance vision, color vision, peripheral vision, depth perception, and the ability to adjust focus

Please note this job description is not designed to cover or contain a comprehensive listing of activities, duties, or responsibilities that are required of the employee for this job. Duties, responsibilities, and activities may change at any time with or without notice.

At We Insure, Group our values shape how we work, how we lead, and how we grow—together. They’re more than just words—they guide every interaction, every decision, and every customer experience.

• We personalize protection at a price you can trust
• We hustle to find opportunity
• We care authentically
• We thrive in ambiguity
• We own our results
• We have fun along the way
• And—we’re just getting started

This position is not able to be performed in California, Colorado, New York or Washington.

We Insure Group is an equal opportunity employer that does not discriminate on the basis of race, color, religion, sex (including pregnancy, sexual orientation, and gender identity), national origin, age, disability, veteran status, marital status, or any other protected characteristic. Our hiring practices ensure that all qualified applicants receive fair consideration without regard to these characteristics.

We Insure Group is committed to creating an inclusive and accessible workplace for all candidates, including those with disabilities. We are dedicated to ensuring equal employment opportunities and providing reasonable accommodations to qualified individuals with disabilities. If you require reasonable accommodations to participate in the application or interview process, please contact our HR department at hrinfo@peak6insurtech.com. We will work with you to provide the necessary accommodations to ensure your full participation in our hiring process.

Note to applicant: It is unlawful in Massachusetts and Maryland to require or administer a lie detector test as a condition of employment or continued employment. Please know that our company does not use lie detector tests in our hiring process.

$97,600-$122,000