Join Our Team

Do you have experience working in Benefits and working with employees? Do you enjoy interfacing with other people? If so, we’re looking for you! Web Benefits Design is a fast-growing, award winning company. 

Ready to Make an Impact?

Some of our team building activities include a company picnic at Dave and Busters, holiday parties, comedy club, monthly happy hour, company sponsored Friday lunches during peak season for all employees, unlimited drinks coffee, and more!

Exciting Benefits

We offer exciting and challenging projects with industry leading companies, competitive health benefits, flexible work arrangements, ongoing career development, company outings and tons of other fringe benefits!

Our Philosophy

We respect your skills, ideas and contributions – and provide an entrepreneurial environment where you can make things happen. Your voice and your opinions matter!

Join our team – apply today.

Website Content Specialist

This position will assist in the process of completing various html updates and initial website builds (from an existing system PHP template) as well as other duties assigned. You have the ability to increase in both salary and position based on your ability to learn our business and add value to our team. Overtime during busy months is expected and required. Basic html5, CSS3 PHP knowledge desired.  Cross platform browser testing (including mobile and tablet devices).  HTML code editor knowledge required.  Adobe Creative Cloud knowledge (Acrobat Reader, InDesign, DreamWeaver required).  Attention to detail and 100% accuracy for data entry.

Call Center Specialist (Bi-lingual candidates are a plus)

Successfully answer and resolve every benefits hotline call that you receive or initiate to help ensure client satisfaction and retention. Partner with the Account Management team to handle special projects and additional services per client as needed.   Candidates will be trained on all call center clients and will be required to learn how to navigate their website and online enrollment system, learn about their benefits and eligibility detail so that they can assist every caller with any questions, issues or concerns.  Ability to communication with others professional with  accurate spelling, proper use of capitalization, punctuation, and sentence structure required. 

Benefit Services Account Manager/Sr. Benefit Services Account Manager

The Benefit Services Account Manager or Sr. Benefit Services Account Manager will lead client facing consulting activities to help the client realize their objectives and ensure ROI. This role will monitor and coordinate the ongoing efforts of teams and multiple departments and will be a liaison between WBD and our customers. Responsible for proactive, creative relationship-building with customers and brokers. Emphasis is on client retention and upselling products and services. This position requires someone who is highly organized, has excellent communication skills and displays good judgment.

5+ years’ experience in sales and customer service management along with technical knowledge relevant to the benefits technology industry required. Familiarity with field’s concepts, practices and procedures. Able to rely on experience and judgment to plan and accomplish goals. Self-motivated; with good planning and analytical skills, the ability to develop deep understanding of the technical and business challenges our clients face. Must be able to identify opportunities to increase sales of products and services to meet those needs.

Benefit Data Analyst (Excel skills required)

The EDI Account Executive will be part of the Data Connections department, supporting all phases of  implementation in the Web Benefits Design’s Total Access Exchange enrollment platform.  This position will be responsible for troubleshooting and resolving errors utilizing Excel.  Participation in all phases of  implementations (initiation, build, test, production).   Perform testing and thoroughly document progress and issues.  Process and monitor inbound and outbound documents (including TPA agreements).  See that file discrepancies are addressed and resolved in a timely manner.  Work with the technical/development team to identify and resolve issues in a timely manner.  Review documented training material for accuracy and assist in end user training and support .

Regional Sales Representative


Job Summary/Scope:

  • We are seeking outside sales professionals who are motivated, creative and aggressively growth-focused. In this position, you’ll identify and cultivate new prospects inside our three-tier distribution channel: Benefit Brokers, Insurance Carriers, and Human Resource Professionals.
  • This is a “Hunter” position, and as such we’re looking for intelligent, high-character individuals with a track record of success and a competitive fire to win. Outside sales skills are a prerequisite, with experience in Benefits and/or HR an added plus. In this role, you will work smart, work hard, have fun, join a great team of like-minded professionals, and experience a level of success and satisfaction we all strive to achieve! 

Benefits and Perks:

  • Base salary + commissions
  • Full healthcare benefits package + 401k match
  • Travel and expense allowance
  • Established and Protected Sales Territories
  • Tuition Reimbursement and Scholarship Programs


  • 2-10 years of outside sales experience
  • Experience selling healthcare insurance, PEO’s and/or HR technology
  • Experience as a broker, or calling on the broker community, is a bonus
  • High school diploma required. Bachelor’s degree in related field preferred
  • Must have a hunter mentality and an entrepreneurial drive
  • Ability to prospect, cold call, and develop new business relationships over the phone and in person.
  • Self-motivated entrepreneur who can work effectively on a team as well as individually.

Essential Duties:

  • New clients, new brokers, new logos, new business.
  • Generate new sales opportunities.
  • Establish new relationships with brokers, carrier reps and HR professionals that result in closing business.
  • Reach or exceed assigned sales goals within territory. Expectation is to close average of 2 new deals per month.
  • Meet activity expectations of 50 substantive interactions per week, and 5 face-to-face meetings/demos per week.
  • Results oriented: understand where you are against all established goals, make corrections and adjustments accordingly.
  • Connect customers’ business needs with Web Benefits Design’s products and services.
  • Have the ability to provide an overview of Web Benefits Design Portfolio of Products & Services in written form and verbally. Must know how to answer basic questions about our service offerings. Demonstrate ability to articulate Web Benefits Design value messaging.
  • Demonstrate technical, product & industry expertise.
  • Become proficient in our CRM, Salesforce. Dedicated to data quality and meticulous population of key sales information.
  • Devoted to continuous learning of industry – trends, competitors and the market.
  • Strong interpersonal skills: must be able to build positive relationships both internally and externally to achieve success.

We mean business – but we have fun!


Competitive Salary

Medical, prescription, dental and vision coverage

Short and long term disability coverage


Life and AD&D benefits


Voluntary life insurance

401K retirement plan

Paid vacation and sick time

Career development opportunities

Employee referral bonus programs

Free polo shirts

Free parking

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