Compliance guides and resources

Running a business can sometimes be exhilarating work, but it can also come with its fair share of tedium—thanks to the long list of tasks associated with compliance. Filing an annual report in your state of incorporation—and any additional states where you’re registered to do business—is one of those tasks. And like many business compliance tasks, the specific requirements to file vary from state to state.

HR compliance has two main parts. First, you need to identify the laws and regulations that apply to your business, and then, you need to comply with them. Both can be tricky. Businesses need to comply with federal, state, and local laws in every jurisdiction where they employ workers. Laws also change all the time, and government agencies won’t notify you of changes—it’s your job to stay up to date.

At its most basic level, workers’ compensation is one of the simpler compliance requirements for employers to navigate. You either need to carry it, or you don’t—and because most US states require employers to carry workers’ compensation coverage, if you have employees, you’re likely to need coverage. But here’s where it can get thorny: Workers’ compensation requirements are determined by state law, and authorized providers, required benefits, and exemptions vary by state. When you’re juggling countless other tasks related to business compliance, the details related to workers comp can fall through the cracks.

If you work with a professional employer organization (PEO), it’s a good idea to regularly reevaluate the relationship. Growing businesses can reach a point where the costs of working with a PEO outweigh the benefits, and some companies expanding into new states may also run into limitations on what PEOs can do there—eliminating the PEO’s original value proposition. If you’re dissatisfied with your PEO or your business circumstances have changed, it may be time to leave.

Conventional wisdom holds that only death and taxes are certain. The tricky part, however, is that sometimes tax obligations aren’t certain. For multi-state business owners, determining what you owe (and where you owe it) can be complicated. Consider the following brain-teaser: A Wisconsin-based DTC pickle company grows cucumbers outside of Milwaukee, pickles them on site, and ships them to individual consumers all over the country. As the business grows, it retains the help of a New Jersey-based marketing professional and a fulfillment consultant in Michigan. Where does this business owe state taxes? In Wisconsin only? In Wisconsin, Michigan, and New Jersey? In every state where a consumer buys a pickle?

Let’s say that you own a tomato farm in Iowa. You harvest your own seeds, grow your tomatoes in Iowa soil, harvest your tomatoes with a local workforce, and sell them at a local farmers markets. Congratulations—you own a single-state business, and you don’t need to worry about foreign qualification. But what if you’re a startup founder who is building a platform to connect farmers to restaurants and boutique grocery markets in their region? You might be based in Chicago, but you hire engineers based in Texas, and you’re growing a user base nationwide.

Some people love to follow the rules–others live to break them. Many founders and business owners fall at least partially into this second category. After all, innovation requires questioning the status quo. But one area where it’s wisest not to break rules is the law. Employment and tax laws apply to even the earliest stage, most disruptive founders, and not complying comes with penalties and fines. That means when it comes to business compliance, you need to become a certified box-checker.

The decision to hire remote workers can transform your business. You’ll have access to a national (or even global) talent pool, save on overhead costs, and provide a valuable incentive to join your team: According to a 2022 Future Forum study, 80% of knowledge workers desire a flexible work location. Remote work can also increase employee satisfaction and productivity, improve work-life balance, and even support diversity and inclusion—employees who lack transportation, can’t afford to live near the office, or even need to pick up the kids every day at noon won’t necessarily be precluded from full participation.

Consider the following scenario: You’re the founder of a new startup, which you incorporated in Delaware, but you live in California. You need to register your company as a foreign entity to do business there. But before you can register in California, you’ll need to obtain a Certificate of Good Standing from your incorporated state of Delaware. Essentially, a Certificate of Good Standing validates the legitimacy of your business. Business owners might use a Certificate to register to do business in another state, apply for a business loan or insurance, seek financing from investors, or lease commercial space.

We’re thrilled to announce the launch of Guide to Starting a Remote Company created in partnership between Mosey and Stripe. As the founder of Mosey and former product development lead of Stripe Atlas, I’ve heard from thousands of founders about the challenges they face when starting and running a remote business. More startups than ever[0] are starting fully remote, taking advantage of the rise of digital tools and technologies to work from anywhere. However, remote startups often run into complicated compliance challenges much earlier in their development than their in-office counterparts, which can be distracting and expensive.