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Diversified Benefit Services, Inc. (DBS) is an industry leading third party administrator of FSAs, HRAs, HSAs and COBRA. We have provided excellence in benefit plan solutions for over 30 years. At DBS we believe that good people are the key to our success and we understand the importance of finding qualified, motivated and positive professionals. We look for team-oriented individuals seeking opportunity in a challenging and rewarding work environment.
DBS is privately owned and is located west of Milwaukee in Hartland, Wisconsin. We offer a quality work environment and a competitive salary and benefits package.

How to Apply

To apply for a position at Diversified Benefit Services, Inc.,
please e-mail your resume and salary requirements to:

Current Openings

Accounting Assistant

The primary emphasis in this role includes auditing and reconciliation of financial transactions, invoicing client accounts, overseeing ACH transfer of funds and accounts payables/receivables.

Essential Job Duties and Responsibilities

Banking Functions

  1. Perform daily banking audits to reconcile client accounts and review client ACH and wire transfers.
  2. Process high volume of daily banking files.
  3. Process voids/stop payments/reissues.
  4. Daily audit of corporate bank accounts.
  5. Work with clients on set-up for ACH payments.
  6. Bank set-up for all business accounts (FSA, HRA, HSA, and COBRA).
  7. Trouble-shoot banking issues and help identify solutions.  Work directly with banks, IT as well as other internal departments to bring to resolution.

Account Receivables/Payables

  1. Process all incoming payments (check and ACH)
  2. Enter all incoming bills.
  3. Generate checks and submit payments to vendors.
  4. Process internal staff expense reports and issue payments.
  5. Generate and process monthly agent commission reports and issue payments.

Client Invoicing Functions

  1. Develop strong working knowledge of plan billing process and nuances that may affect client invoicing.
  2. Generate monthly client invoices utilizing internal spreadsheets and QuickBooks.
  3. Perform audits on all invoicing.
  4. Respond to client invoicing inquiries.
  5. Generate monthly statements, identify past-due accounts and send notifications to clients.
  6. Identify accounts requiring suspension, initiate process for suspension and complete internal communications as well as pulling of funds electronically.

Required Work Skills

  1. Strong numbers aptitude, enjoy working in a fast-paced, deadline driven environment with a high volume of data.
  2. Proficiency in QuickBooks (or similar accounting software) or higher level experience with Excel spreadsheets.
  3. Demonstrated Accounts Payables/Receivables and invoicing experience.
  4. Understanding of ACH and NACHA file processing.
  5. Outstanding organizational and analytical skills, meticulous attention to detail and thorough follow up skills.
  6. Ability to identify, resolve and escalate issues.
  7. Professional and positive interpersonal skills, high degree of confidentiality, and self-motivated with the ability to effectively manage multiple tasks and prioritize without sacrificing quality.

Claims Specialist

Claims Specialists are responsible for day to day plan administration of pre-tax benefit plans for an assigned group of clients. This high volume, fast paced position requires strong multi-tasking and organizational skills, and includes a high volume of claims processing, issuance of reimbursements, status changes, enrollments, responding to client and participant inquiries and implementation of plan set ups/changes.

Essential Job Duties and Responsibilities

1. Provide a high level of professional service to DBS clients and benefit plan participants.
2. Responsible for day to day plan administration of pre-tax benefit plans for assigned group of clients. Includes a high volume of claims processing, issuance of reimbursements, plan changes, status changes, enrollments, responding to client and participant inquiries, plan set-up in administration software and implementing plan changes.
3. Effective regular communication with clients via phone and email regarding plan changes, claims processing, updates, questions, etc.
4. Master various PC applications and learn software programs quickly.
5. Maintain current working knowledge of benefit plan designs and IRS regulations regarding plans.
6. Accurately enter and audit participant claims and determine eligibility for reimbursement.
7. Generate reports and audit accuracy of information.
8. Provide assistance to Customer Service Team during peak times when we experience increased claims and call volume.
9. Assist with basic office coverage for team members who are out of the office.
10. Work directly with all company departments to ensure client requests are met and a high level of service is consistently provided.

Required Work Skills | Qualifications

1. Proven ability to provide a high level of customer service.
2. Possess excellent organizational, detail orientation, follow through, analytical and problem solving skills.
3. Possess basic math/accounting competencies required within position.
4. Effective multi-tasking skills.
5. Excellent interpersonal skills and demonstrated professionalism.
6. Ability to quickly change gears and demonstrate flexibility.
7. Proficient in the use of computers and possess the ability to quickly learn new software programs.
8. Solid working knowledge of Microsoft Office (including Excel).
9. Able to effectively work with personnel of varied skill levels and work through challenging situations efficiently.
10. Able to handle high volume of information confidentially.
11. Minimum of two years of experience in a professional environment working directly with customers.
12. Previous experience in a claims processing, human resources, and payroll, banking or insurance environment is required.

Compliance Specialist

Compliance Specialists serve as an internal information resource for our front-line service team. The primary function of this role is to dig into various information sources, conduct research and provide answers/guidance on regulations regarding FSAs, HRAs, HSAs and COBRA.  Compliance Specialists help ensure that our Company and our Clients administer benefit plans that are in compliance with applicable regulations.

Essential Job Duties and Responsibilities


  1. Research and provide written responses to compliance related questions from internal departments.
  2. Develop comprehensive knowledge of regulations regarding FSAs, HRAs, HSAs and COBRA utilizing resources such as EBIA manuals, ECFC releases and industry blogs/newsletters.
  3. Review and interpret legislative changes and provide understandable written overview to internal staff and clients.
  4. Develop thorough understanding of required non-discrimination testing, run tests and provide answers to client questions.
  5. Develop understanding of and become proficient in preparation of plan documents.
  6. Assist in preparation of written client and business partner informational releases regarding regulations, plan updates, action needed, deadlines, etc.
  7. Maintain easy to use compliance related resource materials for internal staff members.

Required Work Skills / Experience

  1. Desire to become an expert in FSA, HRA, HSA and COBRA compliance.
  2. Strong written and verbal communication skills combined with ability to break information down into understandable language and concepts for end users.
  3. Skill and interest in conducting research and interpreting information.
  4. Experience preparing professional written documentation and correspondence.
  5. Possess strong critical thinking skills and have the ability to compare and contrast various information sources.
  6. Demonstrate meticulous attention to detail.
  7. Ability to interpret technically written regulations and regulatory communications.
  8. Strong time management, researching and organizational skills in a deadline driven environment.
  9. Minimum two years of experience in a benefits, insurance or human resource environment.  Prior COBRA, health insurance or employee benefits compliance/research experience a plus.

Customer Service Representative

Customer Service Representatives (CSRs) are responsible for providing exceptional phone service to plan participants as well as the accurate screening/entry of Flexible Benefit Plan and Health Reimbursement Arrangement claims.

Essential Job Duties and Responsibilities:

  • Learn and effectively apply claims processing procedures.
  • Communicate professionally on the phone with plan participants.
  • Educate participants and resolve claim issues.
  • Perform report audits.
  • Enter benefit plan enrollments.
  • Professionally de-escalate challenging participant calls.
  • Master software programs utilized for claim entry.
  • Work effectively with varied levels of personnel.

Required Work Skills:

  • Proven ability to provide a high level of customer service.
  • Possess proficient data entry and keyboarding skills.
  • Ability to effectively work with plan participants over the phone.
  • Possess strong attention to detail and demonstrate a high level of accuracy in work.
  • Previous customer service experience required.
  • Previous experience in a claims or insurance environment is a plus.

Sales Executive

The role of the Sales Executive involves direct sales of DBS services to customers. (Customers include clients, prospects, agents and agencies).  One of the most important objectives is to reach or exceed the individually established sales goal for the fiscal year.  This position reports directly to the Sales Manager.  The compensation plan has three components consisting of base compensation, commissions and bonus.

Essential Job Duties and Responsibilities

Direct Sales Responsibilities:

  1. Achieve individually established fiscal year sales revenue goal for DBS services including FSA, HRA, HSA, MBP and COBRA.
  2. Build business by identifying and selling DBS services directly to prospects. (Prospects include clients, prospects, agents and agencies).
  3. Determine business opportunities by identifying prospects and researching sales options
  4. Selling DBS services by contacting and developing relationships with prospects that should include cold calling, emailing, canvassing, webinars, new technology outreach and other innovative methods that result in new sales development opportunities.
  5. Ensure timely follow up with prospects.
  6. Participate in networking opportunities to increase new sales.
  7. Close sales with prospects from sales activities.
  8. Attending various trade shows, conventions and conferences.
  9. Conduct client service calls and other functions to ensure retention of DBS clientele.
  10. Maintain in DBS’ CRM system up to date records of sales related functions: calls, client visits, emails, etc.
  11. Contribute to the sales team effort by accomplishing sales results.

Sales Support Functions:

  1. Provide input to the sales team regarding sales ideas.
  2. Attend and actively participate in company and sales department meetings as scheduled.
  3. Provide Sales Manager with requested reports (sales presentations, cold call/prospective client lists, etc.).
  4. Maintain good working relationships with Sales Department personnel.
  5. Other sales support functions, as may be warranted.

Sales Administrative Support Functions:

  1. Follow established procedures and methods for DBS services.
  2. Work effectively with Client Services personnel on sales related activities.
  3. Provide complete and accurate Plan Design Guides for new clients.
  4. Conduct clear and effective group presentations and webinars for plan participants.
  5. Enter pertinent client notes in software system.
  6. Communicate directly with Claims Department Management on client/participant issues.
  7. Participate in key client conference calls.
  8. Maintain good working knowledge of DBS software.
  9. Other sales administrative support functions, as may be warranted.

Position Requirement Skills

  1. Proven sales experience and motivation preferably within DBS related services.
  2. Ability to meet sales goals and be successful within a base, commissions and bonus compensation environment.
  3. Be a quick learner of DBS services and our differentiators in the market place.
  4. Strong sales prospecting, sales planning and closing skills.
  5. Possess excellent customer service skills including effectively and efficiently handling client challenges.
  6. Ability to represent and maintain professional standards and image of DBS with customers and fellow employees.
  7. Ability to learn, retain, and clearly communicate the rules and regulations of the plans that DBS administers.
  8. Demonstrate excellent organizational, schedule coordination, detail, follow-through, analytical and problem solving skills.
  9. Ability to multi-task yet work independently and supportively within a team environment.
  10. Able to meet with customers or prospects on or off site.
  11. Ability to successfully provide customer employee benefit meetings, orientations and training sessions as requested.
  12. Able to handle confidential Personally Identifiable Information (PII) & Private Health Information (PHI) in an appropriate manner following company guidelines and policies.
  13. Possess accurate administrative skills related to this position.
  14. Possess basic math/accounting competencies required within position.
  15. Able to work in a varied, fast-paced, changing environment and accept change positively.
  16. Able to work effectively and efficiently with varied and diverse levels of customer personnel and employees.
  17. Able to travel statewide and out of state to meet job duties and responsibilities.
  18. Able to meet and maintain established physical and environmental job requirements.
  19. Other functions, as may be warranted.