Your fate lies behind these walls of text. This, my friends, is what it’s like to choose your health insurance. And your choices are hidden in a page that’s black with small print, written in a language you don’t understand, and littered with numbers that frighten you. So let’s demystify your SBC (summary of benefits and coverage) so you can make good decisions.

Life and AD&D is one of the last benefits that small businesses and startups add to their offerings. It’s a real bummer to talk about. And unlike short-term disability, the people who need it don’t complain if you don’t have it. But here are some reasons you should care about life and AD&D insurance.

The One Big Beautiful Bill Act (OBBBA) increased your health insurance premiums in two meaningful ways: It cut pandemic-era premium tax credits (which help the working poor get healthcare) and it cut funding for Medicaid (which pays for healthcare for the very poor).

I get that it’s expensive to pay someone not to work for several months, but there are strong business reasons why you should do it anyway. 

What if, instead of inflating wages with cash, the company offered to pay for something even more valuable than cash? The health of workers and their families. 

Insurance premiums have been increasing at more than double the rate of inflation for the past 3 years. In 2026, employer group plans are expected to increase nearly 8%. 

Let's get one thing straight: It's perfectly fine for your company to reimburse people for having a life. But if there's no business purpose or tax-preferred program for it (like an HRA, commuter benefit, or 401k), it has to be taxed as income. 

A PEO is an insurance broker, a guardrail, and a payroll provider. But it’s not a brain. Some people need a PEO. Some need a person. Most don’t know which they are.

What we’re really seeing is misaligned incentives disguised as authority. They have no reason to follow through, just respond. We wouldn’t put up with this in any other business service.

Parental leave combines the most complicated parts of HR into one policy: protected classes, disability, paid time off and sick time, obscure payroll esoterica, employees who are "active" but not "working" (and sometimes don't come back when you expect), insurance (policy details, deductions, and a qualifying event), onboarding and offboarding (maybe more than once per person), a bajillionty federal, state, and local laws, many of which conflict

Even the fancy ben admin tools. Somewhere behind the curtain, someone is downloading a form and forwarding it to a carrier. Often using unsecured email.

"Is this because I said I wasn't pregnant?" He scratched his beard. He was the first non-birth parent to use the policy. And it wasn’t working as planned. And yes, his claim was denied because he wasn't pregnant.

Everywhere I went, I saw the same thing: Employees didn’t understand what they signed up for. Brokers didn’t really understand either. HR didn’t want to touch it. Claims were denied. People thought their plans sucked.

Both employers and employees get 1.5x the value of every dollar compensated through a tax-sheltered program that they do through straight co

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Read on for 12 practical tips on how to structure and present your employee benefits to get the most out of your organization’s greatest ass

Your employee benefits are a big investment. Make sure that your benefits package supports your employees’ productivity and sends a message