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Do I need to tax my "fun" stipend?
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.
Claire Baker
2 min read


Do you really need a PEO? Here’s how to tell
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.
Claire Baker
6 min read


Why is my insurance broker so unhelpful?
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.
Claire Baker
2 min read


Is unlimited PTO really "unlimited"?
Somewhere between two weeks and thirty years, it has to become something else.
Claire Baker
2 min read


FMLA is outdated in a remote world
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.
Claire Baker
2 min read


The Parental Leave Trap: Employee handbook edition
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
Claire Baker
8 min read


Behind the Benefits Curtain: It’s Just Tina and a Fax Machine
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.
Claire Baker
2 min read


401(k) Compliance isn't always automatic
We knew the compliance risks when we picked the non-Safe Harbor 401k option. We thought we were keeping an eye on it.
Claire Baker
2 min read


Take the drama out of Parental Leave
"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.
Claire Baker
2 min read


Insurance isn't a scam (probably)
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.
Claire Baker
2 min read


Hacking a health plan: Finding flexibility in a QLE
I don't know who needs to hear this, but Qualifying Life Events (QLEs) aren't written in stone.
Claire Baker
3 min read


This is why you hate insurance
These problems don’t show up right away. They lie in wait until someone balances the books and notices thousands of dollars missing.
Claire Baker
2 min read


When the Worker's Comp Board goes overboard
A man claiming to represent the New York Workers' Comp Board had shown up at my client's home in upstate New York, demanding proof of coverage. It would have been laughable, except that it was real.
Claire Baker
2 min read


FMLA: What it is and what it isn't
FMLA doesn't guarantee paid leave, but some states have paid leave programs.
Claire Baker
5 min read


Meal and Rest Break Regulations by State
Breaks shorter than 30 minutes aren't required under Federal law. Breaks under 20 must be paid and included in overtime, PTO, and FTE calcul
Irshad Ullah and Claire Baker
7 min read


PEO or no? A deep dive into payroll models
Running the People side of your business takes a lot of work, but hiring a PEO comes with trade-offs that you may regret later.
Claire Baker
7 min read


How to put thousands into your employees' pockets for next to nothing
Both employers and employees get 1.5x the value of every dollar compensated through a tax-sheltered program that they do through straight co
Claire Baker
8 min read


Selecting employer-sponsored health insurance
In this post we’ll discuss how to determine your budget and priorities, what information to look for in plan options, and how to structure a
Claire Baker
7 min read


Commuter Benefits
Offering a commuter benefit to your employees can make a meaningful difference in your team’s quality of life, improve productivity, and pot
Claire Baker
4 min read


Everything you need to know about COBRA
Given the significant cost of many COBRA premiums, PeopleOps teams should be prepared to answer departing employees’ questions about COBRA i
Claire Baker
7 min read
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