The many layers of humans and technology that go into insurance deductions can make it hard to track down where the problem is. And because of the old school systems insurance companies still use, it can be like traveling back in time. 

Nearly everything that happens in the company goes through payroll. And the person managing it needs to have the skills of an accountant, IT, lawyer, insurance agent, and operations manager, all rolled into one.

For years, health insurance costs have already been increasing at more than double the rate of inflation. But even factoring in that trend, next year’s numbers seem like a prank. 

Both of these tools are available to companies for less than a dollar per employee per month. They can transform someone’s exit from cold paperwork to meaningful support.  If it rips your heart out to see what’s happening in the job market, Callings and Kept are two things you can offer right now that make a real difference.

You’re probably sleeping on the biggest company perk just because you think it isn’t free. You may think you’re maximizing the company perks, but if you aren’t maxing out your 401(k), you’re playing like an amateur. 

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%. 

Short term disability insurance (STD) isn’t sexy. It doesn't attract top talent, but it can keep a company from the kind of tough decisions that can end with lawyers. Many employers don’t even know that the situations that are draining their budget are insurable. 

Is it okay for an hourly employee to work 30 hrs/week (instead of 40) for 3 weeks due to illness without taking intermittent FMLA? Their manager is cool with it and the employee doesn't want to take PTO.

He was quite confident that people always know when their paycheck is wrong. I wish that were always true. Payroll is complex, and you don’t know what you don’t know. I see a ton of these kinds of silent errors with 401(k)s. 

Employers have discretion about what's covered in their HRA plan, which is what makes them so useful. The company decides the annual limit, as well as specifications like whether to cover deductible expenses, post-deductible expenses, and/or over-the-counter expenses and services.

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.

Somewhere between two weeks and thirty years, it has to become something else. 

And yet, if 50 of your employees can’t meet at Applebees after work, someone taking leave might not have legal job protection. Even if the work is covered. Even if the team has capacity. Even if the impact is minimal.

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.

We knew the compliance risks when we picked the non-Safe Harbor 401k option. We thought we were keeping an eye on it.

"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.