As you’ve probably figured out by now, the answer is no, because it’s not at all clear how or even if ADA rules will be applied to any particular website. Still, it’s generally a good idea to err on the side of caution. Many states have adopted their own accessibility laws, and the volume of accessibility-related lawsuits filed against websites has ballooned in recent years. Plaintiffs have been more successful in these suits than ever before. With no clearly defined regulations to follow, it is probably not worth it for most companies to gamble that a court will rule in their favor.
The ADA guidelines are often updated so that businesses can better understand how various disabilities can affect the way that people will interact with websites and digital content. The guidelines also explain why certain barriers can prevent disabled individuals from using or even accessing a website. With these goals in mind, it is important to note that organizations need to review the guidelines on a yearly basis. New technologies, such as Artificial Intelligence10, are being used to help people with disabilities get the most out of the digital world. If organizations fail to read the latest ADA guidelines, then they will soon discover that their approach to web accessibility is outdated, and they might be in violation of digital accessibility laws.

Case law has been the most helpful in illuminating the implications of the ADA for websites.There have been lawsuits involving companies like Expedia, Hotels.com, Southwest Airlines, and Target as defendants and primarily featuring accessibility organizations as plaintiffs. These cases had mixed results, but each helped clarify the ADA's jurisdiction on the web. 
Because web designers tend to work as freelancers on a project basis, they must be excellent communicators, willing to manage their own work, and available on your schedule. Some critical skills, such as working collaboratively and responding enthusiastically to feedback, aren’t core to good web design, but make working with a web designer much easier. Finally, look for a web designer who has cross-functional knowledge, such as understanding marketing and conversion rate optimization in addition to web design.

So, what do I mean by that? That sounds weird. So, when I say designer, I mean someone who's strictly an artist, and there's a lot of those out there. A lot of 'designers' are only concerned about the aesthetics of the site. What it looks like, or if its unique, or if it follows the latest website design trends. But at the end of the day they don't really 'get it' when it comes to what the primary purpose of a website is.

You are correct, ADA defines an “employer” as any person who is 1) engaged in an industry affecting commerce; 2) employes 15 or more full-time employees each work day; and 3) for at least 20 or more calendar weeks in the year. In the context of physical spaces, ADA would not apply to companies with fewer than 15 employees. However, courts don’t seem to have come to a consensus on what digital compliance really should look like. Because websites can be accessed anywhere in the country, small business owners might potentially face lawsuits in unfavorable jurisdictions. If you are a small business owner, I would recommend consulting with an accessibility lawyer and ask what they recommend.
This is the reason why I think web design firms have to position themselves as solution providers and not just web guys/gals. A client doesn't need a website, they need sales. The website is just part of that solution but it's not the solution and unlike web design, service like email marketing automation, SEO, and PPC requires an experienced professional.
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Luckily, the international nonprofit World Wide Web Consortium (W3C) brings together smart people who develop open standards to ensure the long-term growth of the Web. They produce recommendations for making websites fair and equally accessible for the highest number of people possible. Their Web Content Accessibility Guidelines (WCAG) 2.1 offer clear guidance for web developers to achieve ADA compliance.
The gray area is a matter of scale and purpose. If you have a small business which serves as specific market it's a good idea to make the site as user and disability friendly as possible. If, however, your market serves segments with a likeliness to have various handicaps or disabilities you should address that with an ADA Compliance review of the site. Also consider the scale and purpose of an organization. Publicly traded large businesses need to concern themselves more than a single location family owned retailer and if someone sues your flower shop because the text was too small or didn't have "image alt tags" causing them distress... That's pretty frivolous and would likely not stand.

The ADA statute identifies who is a person with a disability, who has obligations under the ADA, general non-discrimination requirements and other basic obligations. It delegates fleshing out those obligations to federal agencies. The agencies issue regulations and design standards. The regulations have the details on the rights of people with disabilities and responsibilities of employers, state and local governments, transportation providers, businesses and non-profit organizations. The design standards specify how many entrances need to be accessible, how many toilet rooms and the design for those elements.  To know what the ADA requires, you need to read the law, regulations and design standards.  
Any business that is considered a “place of public accommodation” is required to provide equal access to services under the nondiscrimination requirements of Title III of ADA. When you look at the guidelines closely, this includes hotels, entertainment venues, legal and accounting firms, retail stores, and virtually every business that is not a private club, including businesses that exist solely on the web. 
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