Back To Top


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 35 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.

Interested in applying?

Please e-mail your resume to:

Current Openings

Sales Executive

We are expanding our sales team and are seeking an experienced direct business to business consultative sales professionals who knows their way around the benefits and/or insurance industry.   This is an excellent opportunity to join a quality organization with an exceptional work environment and a skilled professional sales team.  DBS offers an excellent base salary with lucrative commission compensation potential and benefits package.

Key Responsibilities

  • Effective networking and prospecting of target clients including private, public and non-profit employers.
  • Maintain strong working relationships with established benefit brokers, insurance agents and agencies and new accounts within regional and national territory.
  • Proficiently network and prospect employers, agents and agencies including ‘warm’ and ‘cold’ calls to maintain and expand client base.
  • Direct sales activities to expand market share involving our benefits related products.
  • Meet or exceed sales objectives and track work activities using the CRM system.
  • Conduct group meetings and presentations to educate participants and communicate plan guidelines.
  • Attend conferences, tradeshows, workshops and seminars to learn and to promote DBS services.


  • Minimum of 5 years of direct business to business sales experience (preferably within the insurance or employee benefits arena).
  • Experience selling “administrative type services” is a plus.
  • Enjoy being part of a service based company.
  • Values a solid base compensation and motivated by commission incentives.
  • Highly self-motivated, ethical and reliable.
  • Excellent verbal and written communications skills.
  • Skilled at building and maintaining positive client, broker and agent relationships.
  • Able to travel in pursuit of sales and servicing clients. (Bulk of travel is within Wisconsin and accomplished within the day.)

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 skill 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

  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 information confidentially.
  11. Minimum of two years of experience in a professional work environment working directly with customers.
  12. Previous experience in a claims processing, payroll, banking or insurance environment is required.

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 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 sales 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.

3.  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. Experience in employee benefits or health insurance industries preferred.
  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 Plan and Health Reimbursement Arrangement claims.

Essential Job Duties and Responsibilities:

  1. Learn and effectively apply claims screening procedures.
  2. Communicate professionally on the phone with plan participants.
  3. Educate participants and resolve claim issues.
  4. Perform report audits.
  5. Enter benefit plan enrollments.
  6. Professionally de-escalate challenging participant calls.
  7. Master software programs utilized for claim entry.
  8. Work effectively with varied levels of personnel.

Required Work Skills:

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