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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

Client Services Specialist

Client Services Specialists are a primary point of contact for clients, internal staff and insurance brokers and play a key role in the onboarding of new clients, resolving service issues, maintaining high levels of client satisfaction and providing ongoing sales and client support.

Essential Job Duties and Responsibilities:
1. Play lead role in new client onboarding

  • Serve as primary point of contact for clients, insurance brokers and internal departments throughout the new client implementation process.
  • Assume lead coordinator role for the onboarding of new clients, review/audit of plan design details and gather required information and forms.
  • Enter client data and plan details in Access database and administration software.
  • Coordinate enrollments and the creation of legal plan documents including Service Agreements, BAA/HIPAA and SPDs.
  • Work with assigned Claims Specialist to jointly conduct webinar training for clients to educate them on internal processes and use of our online software platform.
  • Identify and communicate opportunities for improvement in our onboarding/implementation process.

2. Provide internal support

  • Provide quotes and complete information about DBS products/services to insurance brokers and potential clients.
  • Communicate with sales team regarding plan options and work through unique plan design requests.
  • Build and nurture strong relationships with insurance brokers/agencies.

3. Client Services

  • Build and nurture strong relationships with clients.
  • Utilize professional written and verbal business communications with clients and brokers.
  • Conduct client surveys to measure satisfaction with DBS services.
  • Liaise between clients, sales executives, insurance brokers and appropriate internal personnel/departments to resolve client servicing issues.
  • Work with clients and agents to obtain plan changes and facilitate internal process to implement changes.

4. Technical/Business/Administrative Skills

  • Maintain current understanding of insurance marketplace and employer pre-tax benefit plans.
  • Maintain thorough understanding of Microsoft Office products including Access and DBS administration software capabilities.
  • Perform other administrative duties as required within the position.

Required Work Skills:

1. Minimum of two years of experience in employee benefits or health insurance industries.

2. Experience working directly with external clients and/or insurance agents.

3. Highly professional verbal and written communication skills.

4. Proficient in the use of computers and software programs.

5. Strong problem solving skills and the ability to understand complex issues.

6. Ability to identify issues and offer potential solutions.

7. Ability to work with internal staff and external clients of varying personalities and skill levels.

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 Plans, Health Reimbursement Arrangements and Health Savings Account 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

Sales Executives are responsible for direct sales of DBS’ services to prospects, current clients as well as insurance agents, brokers and consultants. This position reports directly to the Sales Manager. It provides a salary with commissions.

Essential Job Duties and Responsibilities:

  • Achieve established annual FSA/HRA/HSA participant goals as well as other sales goals.
  • Effectively market DBS services to prospects, current clients and insurance agents/brokers/consultants.
  • Conduct cold calls to prospects via telephone, email, canvassing, seminars, as well as other related methods.
  • Ensure timely follow up on all calls to acquire additional clients for DBS.
  • Participate in networking opportunities to increase future sales of DBS.
  • Close sales with prospects from marketing activities.
  • Promote DBS services and acquire new clients by attending various trade shows, conventions and conferences.
  • Conduct client service calls and other functions to ensure retention of DBS clientele.
  • Maintain in DBS’ CRM system up to date records of sales related functions: calls, client visits, emails, etc.
  • Other direct sales functions, as may be warranted.

Sales Support Functions:

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

Sales Administrative Support Functions:

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

Position Requirement Skills:

  • Proven sales experience preferably within company related services.
  • Ability to meet sales goals and be successful within a base with commission sales compensation environment.
  • Be a quick learner of DBS services and our differentiation in the market place.
  • Strong client sales prospecting and closing skills.
  • Possess excellent customer service skills, which include effectively and efficiently handling client challenges.
  • Ability to represent and maintain professional standards and image of DBS with clients, prospects, insurance agents, brokers, consultants and fellow employees.
  • Ability to learn, retain, and clearly communicate the rules and regulations of the plans DBS administers.
  • Demonstrate excellent organization, coordination, detail orientation, follow-through, analytical and problem solving skills.
  • Ability to multi-task, work independently, and effectively within a team environment.
  • Able to meet with customers and/or potential clients whether on or off site.
  • Able to effectively hold customer, client and/or internal company employee related meetings/orientations and/or training sessions as requested.
  • Able to handle information on a confidential, business appropriate, need to know basis.
  • Possess accurate administrative skills related to this position.
  • Possess basic math/accounting competencies required within position.
  • Able to use job related PC’s and software.
  • Able to work in a varied, fast-paced, changing environment and accept change positively.
  • Able to work effectively and efficiently with varied levels of personnel, a diverse employee/client base.
  • Able to travel within the state of Wisconsin and outside of the state to meet job duties and responsibilities.
  • Able to meet and maintain established physical and environmental job requirements.
  • Other functions, as may be warranted.

COBRA/Compliance Specialist

The Compliance Specialist serves as a DBS expert regarding compliance issues as they relate to Section 125, 105, 223 and COBRA administration.  This is a knowledge intensive position that requires plan and industry knowledge, extensive research, training of internal teams and educating external clients and agents.

Essential Job Duties and Responsibilities:


  • Responsible for overall administration of COBRA benefits for select clients.
  • Maintain a strong working knowledge of COBRA and stay current with law and regulation changes.
  • Ensure plan compliance with IRS regulations and plan documents.
  • Communicate directly with clients, beneficiaries and brokers by phone and through email regarding COBRA; including enrollments, notices, coverages, terminations, reporting and premium payments.
  • Provide a high level of customer service to all clients and beneficiaries, including timely, knowledgeable and professional response to all inquiries via phone, mail and e-mail.
  • Possess a strong working knowledge of software systems.
  • Responsible for software set-up/entry of all new clients and the timely processing of status changes/add/terms.
  • Generate accurate and timely client reports.
  • Work directly with all departments within the company to ensure client requests are met and a high level of service is consistently provided.


  • Possess comprehensive knowledge of required testing of Section 125,105 and 223 plans and perform non-discrimination testing.
  • Research and respond to compliance related questions from internal departments.
  • Gather and analyze complex plan regulations regarding Section 125-FSA, 105-HRA, 223-HSA and COBRA utilizing resources such as EBIA manuals, ECFC releases and industry blogs/newsletters.
  • Review and interpret legislative changes and provide understandable overview to internal staff and clients.
  • Maintain current and thorough understanding of legal plan documents, HIPAA and Business Associate Agreements.
  • Develop resource materials for internal staff members.

Required Work Skills:

  • Desire to become an expert in FSA, HRA, HSA and COBRA compliance.
  • Possess strong problem solving skills and the ability to understand complex issues.
  • Demonstrate meticulous attention to detail.
  • Professional written and verbal communication skills.
  • Experience preparing professional written documentation and correspondence.
  • Ability to interpret statutes, regulations and regulatory communications.
  • Computer competency and ability to quickly learn various software programs.  Proficient data entry and keyboarding skills.
  • Strong time management, researching and organizational skills in a deadline driven environment.
  • Ability to handle multiple assignments efficiently and accurately while meeting strict deadlines.
  • Possess basic math/accounting competencies required within position.
  • Assertive in obtaining information needed to perform job functions in a timely manner.
  • Able to work in a varied, fast-paced, changing environment and accept change positively.
  • Minimum two years of experience in a benefits, insurance or human resource environment.  Prior COBRA or compliance/research experience a plus.


Diversified Benefit Services, Inc. Logo

P.O. Box 260.Hartland.WI.53029 | Phone: 262-367-3300 | 800-234-1229 | Fax: 262-367-5938

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