Employee Benefits

As a small business, we know the demands on your time are many and resources can seem few, especially when it comes your employee benefits plans. Winters-Oliver specializes in working with employers who have 10-99 employees enrolled in group benefits. Following selection of the medical, dental, vision, life, and/or disability plans that are right for your employees, comes the task of getting everyone enrolled. Perhaps you have employees in multiple locations or working remotely and the thought of exchanging countless emails and enrollment applications makes your head spin. Winters-Oliver can relieve that stress and worry through our online enrollment platform.

Employee Benefits

We can provide your group with the following:

  • An online, completely paperless enrollment process that saves you and your employees time and frustration.
  • Real time payroll reduction estimates based on your employees’ plan selections.
  • Employees can request plan changes, including mid-term enrollment changes, through the portal.
  • A completely virtual open enrollment meeting that your employees can view on demand.
  • Completely automated onboarding of new hires and termination of former employees.

Compliance Resources

In addition to helping you improve the way you administer your employee benefits plan, we can also assist with compliance resources such as:

  • Setting up a Premium Only Plan (P.O.P.) so that your employees can pay health insurance premiums pre-tax through payroll deduction.
  • A Wrap Document which includes important notices such as the Summary Plan Description (SPD), Summary of Benefits & Coverages (SBC), COBRA and HIPAA information, waiting periods, plan details and eligibility, etc.
  • Assist you in building the right team to handle COBRA administration and ACA Compliance.

We understand that your human resources department may be limited or perhaps all the human resources responsibilities fall on you as the business owner. If you need a partner who can help lighten the load, then contact Winters-Oliver today!


Electronic Enrollment


Our Services

Attracting and retaining top talent is possibly one of the most difficult tasks of any employer. Having the right strategy is essential, and a robust benefits package is arguably one of the most critical components.

Many small to mid-size employers believe offering an extensive benefit package is out of reach. Some are concerned about the added administrative burden, and others may perceive the financial cost will be too great. However, with the right strategy, funding design, and proper planning, small to mid-size employers are regularly shocked at how easy and achievable it is.

Winters-Oliver Insurance Agency’s comprehensive approach alleviates the administrative tasks associated with employee benefits, maximizes every dollar, and ensures the benefit packages offered appeal to your employees.

From start to finish, we have the expertise, day-to-day support, benefit markets, and technology to make employee benefit management easy and financially attainable for start-ups, small, and mid-size employers.

We Provide

  • Plan design, cost analysis, and underwriting review
  • Varying funding options
  • Defined contribution strategy
  • Multi-plan offerings with creative contribution setup
  • ACA plan design and contribution expertise
  • Benefit communications
  • Benefit enrollment technology
  • Claims support
  • Day-to-day enrollment support and customer service

Benefits Options

  • Medical: Fully insured, self-insured, partially self-insured (level-funded)
  • Dental
  • Vision
  • Ancillary Employer Paid or Voluntary Benefits
    • Life and Accidental Death and Dismemberment (AD&D)
    • Short Term Disability (STD)
    • Long Term Disability (LTD)
    • Hospital Bridge / Hospital Indemnity
    • Medical GAP insurance
    • Accident
    • Critical Illness
    • Cancer
  • Standalone Telemedicine

Flex Services Support

  • Flexible Spending Account (FSA)
  • Health Savings Account (HSA)
  • Health Reimbursement Account (HRA)

Compliance Support

  • COBRA Administration setup
  • Pre-tax and Post-tax strategy
  • Section 125 Plan Document
  • ERISA Wrap Documents