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The First-Timer’s Guide to Employee Benefits: How to Grow Intelligently

By January 28, 2026No Comments

If you’re a business owner looking to enter the employee benefits space for the first time, I have one primary piece of advice: Start small and stay within your comfort zone.

In my years of guiding companies, the biggest mistake I see is a small business “over-promising and under-delivering.” You don’t want to recruit top talent with a flashy benefits package, only to pull the plug six months later because the costs became unsustainable.

Unfortunately, many brokers in this industry just want to sell you a high-dollar policy, collect their commission, and disappear. At Holloway Benefit Concepts, we’d rather help you grow intelligently.

Here is my recommended “Benefit Hierarchy,” ordered from most affordable to most complex, to help you build a package that lasts.


1. Employer-Paid Life Insurance: The Affordable Foundation

This is one of the most cost-effective ways to show your team you care. It provides financial protection for an employee’s family if the unthinkable happens.

  • The Standard: We typically see $50,000 policies for all full-time employees.

  • The Value: While employees aren’t usually beating down your door asking for life insurance, most of them don’t have a personal policy in place. Providing this safety net is a high-impact, low-cost “win.”

2. Vision Insurance: The “Instant Value” Benefit

Unlike life insurance, employees will actively ask for and use vision benefits.

  • The Cost: Usually ranges from $7 to $12 per month for a single enrollee.

  • Pro Tip: Always look for a 12/12/12 plan. This means employees get an exam, new lenses, and new frames every 12 months. Avoid “12/12/24” plans that make them wait two years for frames; saving $1 in premium isn’t worth the frustration it causes your staff.

3. Stand-Alone Telemedicine: The Secret Weapon

Most health plans have telemedicine built-in, but there is a massive advantage to a stand-alone program—especially for part-time staff or those who can’t afford your medical plan.

  • Why it works: For $15–$20 a month, you can cover an employee and their entire household with unlimited $0-copay urgent care and mental health visits.

  • Strategic Advantage: If you are level-funded or self-funded, stand-alone telemedicine keeps minor claims (colds, sinus infections) off your main insurance policy, helping keep your renewals lower.

4. Dental Insurance: Improving the “Chompers”

Dental is a “touchy-feely” benefit—people use it, and they love it.

  • Avoid the “Lazy” Plan: I often see competitors selling $1,500 maximum plans for $50/month. That’s lazy. For just $1 or $2 more, you can often double or triple that maximum to $2,500 or $5,000.

  • The Tax Win: Like vision, dental can be part of a Section 125 plan, allowing you to deduct premiums pre-tax. It’s a win-win for the company’s payroll taxes and the employee’s take-home pay.

5. Disability (Paycheck Protection)

I don’t love the word “disability” because it sounds negative. I prefer Paycheck Protection.

  • Short-Term (STD): Covers about 60% of income for things like illnesses, injuries, or maternity leave (the #1 STD claim).

  • Long-Term (LTD): Kicks in after STD is exhausted and can protect an employee’s income until retirement age.

  • Cost: For a small company, expect to pay between $500 and $1,000 a month for the group. It’s a “life-saver” benefit that employees appreciate most when they actually need it.

6. FSA & HRA: Budget-Friendly Flexibility

If you aren’t ready for full health insurance, these are great alternatives:

  • HRA (Health Reimbursement Arrangement): Employer-funded. You decide the budget and reimburse employees for specific medical expenses.

  • FSA (Flexible Spending Account): Can be funded by employees pre-tax.

  • The Benefit: You aren’t tied to market insurance rates. You set the price and the rules.

7. Health Insurance: The “Necessary Evil”

I saved this for last because it is, by far, your most expensive line item. Average plans start at $500–$600 per employee, and most insurers require the company to pay at least 50%.

My “First-Timer” Tips for Medical:

  1. Look for Underwritten Plans: In Texas, if your staff is relatively healthy, underwritten plans can be 30% cheaper than ACA (“Obamacare”) plans.

  2. Regional vs. National: Don’t overlook regional hospital-system plans. They are often more affordable than the big national names if your employees stay within that local network.

  3. The “Under 50” Rule: If you have fewer than 50 employees and they aren’t demanding medical, avoid it as long as you can. Layer in the other benefits mentioned above first. They provide great value without the $6,000+ per year/per employee price tag.


Final Thoughts

There is no “one size fits all” in benefits. The goal is to find a partner who wants to help your company navigate the space, not just sell you a policy.

If you’re looking for a team that treats your budget like their own, Holloway Benefit Concepts is here to help. Let’s build something your employees love and your bank account can handle.