Demo

Direct Bill and AP Specialist

Robertson Ryan and Associates, Inc.
Milwaukee, WI Full Time
POSTED ON 9/17/2026
AVAILABLE BEFORE 10/16/2026
Recognized nationally as a Top Workplace and Top 100 US Insurance Agency!

Since 1960, Robertson Ryan Insurance has provided comprehensive solutions across Business, Benefits, and Personal Insurance. We proudly serve over 70,000 clients, from small businesses to major national accounts across various industries. With a team of more than 526 professionals and partnerships with over 150 insurance companies, we are the 44th largest Property & Casualty Insurance Agency according to the Insurance Journal. Our dynamic and enjoyable culture is a cornerstone of our success, with many team members having been with us for over a decade. It's an exciting time to join our growing firm!

Summary

Responsible for independently and proactively processing billing transactions in the EPIC system, including entering Direct Bill commissions and invoicing Agency Bill items in accordance with established workflows.

Hybrid/in-office schedule options will be discussed after the training period is successfully completed and are based out of our Milwaukee, WI location.

Essential Duties and Responsibilities

This list of duties and responsibilities is not all inclusive and may be expanded to include other duties and responsibilities, as management may deem necessary from time to time.
  • Reconcile and process carrier commission statements received through the company's third-party processing platform in an accurate and timely manner.
  • Research and resolve direct bill statement discrepancies by working with carriers and internal team members.
  • Invoice all agency bill items as directed by Account Managers on the Billing Request Form in a timely and accurate manner.
  • Research and resolve billing discrepancies, unapplied payments, and outstanding items.
  • Assist in documenting established workflows for all agency invoicing.
  • Collaborate with Account Managers to invoice agency-billed premiums for endorsements, renewals, new business, audits, etc.
  • Work with Account Managers to ensure accurate information is included in EPIC.
  • Maintain organized records and documentation in accordance with company policies and procedures.
  • Maintain a high degree of accuracy in processing agency bill statements and processing carrier payments.
  • Other projects or duties, as needed.


Qualifications

To perform this job successfully, an individual must be able to perform each essential duty satisfactorily. The requirements listed below are representative of the knowledge, skills, and abilities required. Reasonable accommodations may be made to enable individuals with disabilities to perform the essential functions.
  • High school diploma and data entry related experience; or a combination of education and experience.
  • Ability to read and interpret bank statements, commission statements, procedure manuals, and other business documents; prepare reports and correspondence; and communicate effectively with carriers and internal team members.
  • Basic mathematical skills, including the ability to add, subtract, multiply, divide, and calculate rates, ratios, and percentages.
  • Ability to apply common sense understanding to carry out written, oral, or diagram-based instructions and resolve problems involving multiple variables in standardized situations.
  • Advanced knowledge of Microsoft Office products and comfort working with internet-based programs. Applied EPIC experience preferred but not required.
  • Ability to work in a fast-paced environment with minimal instruction while maintaining a high degree of accuracy.
  • Strong organizational skills with the ability to prioritize work, manage workflow, and ensure timely and accurate processing of transactions and responsibilities.
  • Ability to maintain effective working relationships with carriers, co-workers, vendors, and other business contacts while contributing to a team-oriented environment.
  • Commitment to staying informed of industry information, products, legislation, coverages, and technology to support ongoing professional development.
  • Must be willing to work in-office or hybrid at our Milwaukee, WI location.


Physical Demands & Work Environment

While performing the duties of this job, the employee is regularly required to sit, use hands, and communicate effectively. Occasional standing, walking, reaching, stooping, kneeling, crouching, crawling, and lifting up to 10 pounds may be required. Specific vision abilities include close vision and the ability to adjust focus. The work environment is a professional office setting with a moderate noise level. Reasonable accommodations may be made to enable individuals with disabilities to perform the essential functions of the position.

Interested in the position? Apply now or email mstielow@robertsonryan.com!

Additionally, our remote work policy includes having a dedicated, distraction-free workspace. Remote work is not a substitute for childcare, elder care, or other personal responsibilities during working hours.

EEO/AA Statement: Robertson Ryan provides equal employment opportunities to all employees and applicants for employment and prohibits discrimination and harassment of any type without regard to race, color, religion, age, sex, national origin, disability status, genetics, protected veteran status, sexual orientation, gender identity or expression, or any other characteristic protected by federal, state, or local laws.

This policy applies to all terms and conditions of employment, including recruiting, hiring, placement, promotion, termination, layoff, recall, transfer, leaves of absence, compensation, and training.

Attention to all Recruiting Agencies: Recruitment at RRI works on a direct sourcing model. We will contact agencies directly if needed. RRI is not responsible for any related fees for resumes submitted to job postings, our employees or any other part of our company.

Salary.com Estimation for Direct Bill and AP Specialist in Milwaukee, WI
$45,442 to $54,417
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