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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

Administrative Assistant

General Description

Primary emphasis in this role involves coordination of benefit plan enrollments, invoicing for company services, accounts payables/receivables and general administrative duties.  This is a very fast-paced position that provides critical day-to-day support to all areas of the Company.

Essential Job Duties and Responsibilities

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 funds electronically.

FSA Benefit Plan Enrollment Coordination

  1. Work directly with clients to coordinate annual Flexible Spending Account (FSA) enrollments.
  2. Prepare effective tracking system to ensure that all enrollments are received, entered and audited in our software by plan deadlines.
  3. Coordinate distribution of enrollment materials.
  4. Work directly with Data Analysts and IT on importing of enrollment data files.
  5. Assist with audit of annual FSA participant enrollments.
  6. Regularly evaluate and provide input on process improvements to gain efficiency and increase accuracy of enrollments.

Company Administrative Support/Miscellaneous Duties

  1. Serve as back-up for reception as needed.
  2. Send out W-9 Forms as requested by clients.
  3. Collect and process W-9 Forms from vendors.
  4. Complete 1099 Reports annually for corporate accountant.
  5. Generate and track annual client renewal letters for all benefit plans administered.
  6. Form 5500 processing.

Required Work Skills

  1. Proven experience in financial services, benefits, human resources or related industries.
  2. Mid to high level competency in MS Office Suite of products.
  3. Experience working in QuickBooks or similar software.
  4. Exceptional oral and written communication skills.
  5. Strong numbers aptitude, enjoy working in a fast-paced, deadline-driven environment with a high volume of data.
  6. Outstanding organizational and analytical skills, meticulous attention to detail and thorough follow up skills critical.

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.

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

Play lead role in new client onboarding

  1. Serve as primary point of contact for clients, insurance brokers and internal departments throughout the new client implementation process.
  2. Assume lead coordinator role for the onboarding of new clients, review/audit of plan design details and gather required information and forms.
  3. Enter client data and plan details in Access database and administration software.
  4. Coordinate enrollments and the creation of legal plan documents including Service Agreements, BAA/HIPAA and SPDs.
  5. 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.
  6. Identify and communicate opportunities for improvement in our onboarding/implementation process.

Provide internal sales support

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

Client Services

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

Technical/Business/Administrative Skills

  1. Maintain current understanding of insurance marketplace and employer pre-tax benefit plans.
  2. Maintain thorough understanding of Microsoft Office products including Access and DBS administration software capabilities.
  3. 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.

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


  1. Possess comprehensive knowledge of required testing of Section 125,105 and 223 plans and perform non-discrimination testing.
  2. Research and respond to compliance related questions from internal departments.
  3. 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.
  4. Review and interpret legislative changes and provide understandable overview to internal staff and clients.
  5. Maintain current and thorough understanding of legal plan documents, HIPAA and Business Associate Agreements.
  6. Prepare written client and agent network informational releases regarding regulations, plan updates, action needed, deadlines, etc.
  7. Maintain current and thorough understanding of legal plan documents, HIPAA ad Business Associate Agreements.
  8. Develop resource materials for internal staff members.
  9. Assist with office coverage for COBRA team members who are out of the office.

Required Work Skills / Experience

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