Sales tax is complicated. We’ve just gone through the annual flurry of back to school tax holidays, for example. If you’re a remote seller of clothing, you probably sell mostly through retail. But you might have some direct to consumer sales. In some states, you will have to file if you meet the threshold — not just for your direct-to-consumer sales, but for the total revenue. In other states, you might meet the sales threshold, or maybe you did so in a previous year and registered for sales tax compliance, so you have to keep filing even if you have no sales.

For all the states where you’re registered, you must find out when the sales tax holidays are, and whether any of your products are tax-exempt. Sometimes there are price limits, so that items under $100 are tax exempt and higher priced items are not. In Tennessee, belts are exempt but belt buckles are not. Many cities in Missouri decided not to participate in their state’s sales tax holiday. In Illinois, items aren’t tax exempt but rather have a lower tax rate during the holiday. We could go on. And on.

Customer service

Because sales tax regulations are so complex, remote sellers in particular are about ready to give up. You may now have nexus in all 50 states plus the territories, not to mention cities and counties. Any business now can be subject to hundreds or even thousands of jurisdictions. Each jurisdiction may have not only its own definition of taxability and threshold, but also a different calendar for filing.

What’s more, the regulations change frequently. Responses to the changes can’t all be automated. And your business will probably have some specific issues that won’t be automatically covered by a sales tax engine.

You need good customer service.

For many of the pieces in your tech stack, you’re fine with any vendor as long as you don’t have a problem. Web hosting? You’re okay unless you have a problem, and you probably won’t have one even once a year. Phone lines? No problem unless there’s a problem, and most American cities have stable phone service.

Sales taxes? You’re almost sure to have a problem. The entire system is so convoluted that nearly everyone has a problem at one time or another.

So what’s the customer service like with your sales tax solution? One of the biggest sales tax software companies has overseas help desks for all question. If you want to talk with someone in the United States, you have to put in a ticket and you might wait weeks for a response. Oh, and you also have to pay extra.