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Why the linchpin doesn't get promoted
Companies don’t reward you for masking dysfunction. They rely on it. They reward the person patching it up with even more responsibilities. Not the kind that come with a promotion, but responsibilities that come with with more fire drills and more late nights.
Claire Baker
2 min read


Payroll: Mission-critical or a throw-away admin task?
Riddle me this: What responsibility is sometimes handled by senior finance and other times by entry-level HR? What function manages a budget of millions but often gets assigned to the person with the lowest hourly rate?
Claire Baker
1 min read


How to choose payroll software: Know thyself
Choosing payroll software is like tasting wine with the label on the inside: all polish up front and, too often, regret on the back end. By the time you know what’s inside, you’re already seeing double. Picking the best tool is about knowing in advance what “best” means for your working style. The settings you skip during setup are the ones that bite.
Claire Baker
2 min read


How to tell if you're wasting your career at a crappy job
“Everything is broken and I hate it here.” Have you ever worked at one of those places where the work-arounds become the job? Onboarding someone new isn’t about learning your product or roadmap. It’s about learning where the landmines are, how to use The Beast and navigate the playbook.
Claire Baker
2 min read


How does an HRA reduce employers' healthcare costs?
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.
Claire Baker
2 min read


5 Lessons from TechCrunch All Stage '25
Now that anyone can call up the basic skills of any specialization, generalists who know what to call and when will win the market. But now that AI has leveled the playing field, range is what separates those who will make it from those who'll be left behind. Here are my takeaways about what's changed and what hasn't:
Claire Baker
2 min read


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


Why are worker's comp codes so interesting?
If you think that looking up worker’s comp codes is boring, you’re missing out. If you give me a list of thousands of obscure jobs, I’m going to lose at least 20 minutes going through it.
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
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