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.

I recently finished a training in ADA compliance for websites. It was illuminating and daunting, as I realizated that there’s a lot of work to be done. It also reiterated—in no uncertain terms—a gospel I’ve been preaching for several years now. Sites need to be accessible for everyone on every platform. Previously I was just focusing on responsive sites (sites that reformat for the device used, such as a phone or tablet.) Since responsive sites are de rigueur these days, I’d like to focus on your site’s accessibility…can it be accessed by people with disabilities? This includes screen readers and other technology. It’s not just a nice thing, it’s a civil law.
Ensuring your website is ADA compliant takes skill and know-how. Even with drag-and-drop and state-of-the-art web builders, knowing how to put together content, add alt-tags and compliant contrasting colors just to name a few thing, it takes someone familiar with coding, UI/UX techniques and the best practices advised by the W3C (World Wide Web Consortium) to ensure that your site meets at minimum the A Level of Conformance. Here is the W3C’s complete and exhaustive list of technical conformance guidelines.
The U.S. Department of Transportation enforces regulations governing transit, which includes ensuring that recipients of federal aid and state and local entities responsible for roadways and pedestrian facilities do not discriminate on the basis of disability in highway transportation programs or activities. The department also issues guidance to transit agencies on how to comply with the ADA to ensure that public transit vehicles and facilities are accessible.
Offering 29 years of experience in design, I take a lot of pride in every project I take on. I have worked in various printing and advertising agencies since 1991 and my experience includes financial, law, healthcare, retail, real estate, and MLM industries. I own my own graphic design company, Graphical Solutions LLC, so I am not beholden to an outside full-time job and am available to help you whenever you need me.
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.

I should mention one caveat to all of this. Businesses that are required to comply but don't have the ability to bring their websites into compliance can provide an accessible alternative to provide the same information, goods, and services that they provide online, like a staffed phone line. The trick, however, is that this option has to provide at least equal access, including in terms of hours of operation. And, as we know, the internet is around 24/7, so good luck with that. 
Technology is changing, and many website designers are using creative and innovative ways to present web-based materials. These changes may involve new and different access problems and solutions for people with disabilities. This Chapter discusses just a few of the most common ways in which websites can pose barriers to access for people with disabilities. By using the resources listed at the end of this Chapter, you can learn to identify and address other barriers.
The Americans with Disabilities Act (ADA) was developed in 1990 and is meant to ensure that people with disabilities have the same opportunities as anyone else. This means any businesses that serve the public must make sure their building accommodates people with disabilities of various kinds. And now that the internet is so widely used, ADA compliance also applies to websites and even mobile apps. Basically, this means that your website needs to be accessible to people who have disabilities that affect their hearing, vision or physical capacities.
State and local governments will often post documents on their websites using Portable Document Format (PDF). But PDF documents, or those in other image based formats, are often not accessible to blind people who use screen readers and people with low vision who use text enlargement programs or different color and font settings to read computer displays.
These and other types of multimedia can present two distinct problems for people with different disabilities. People who are deaf or hard of hearing can generally see the information presented on webpages. But a deaf person or someone who is hard of hearing may not be able to hear the audio track of a video. On the other hand, persons who are blind or have low vision are frequently unable to see the video images but can hear the audio track.
ADA Compliance is not exactly new, but there is a noticeable increase in lawsuits. but the most important thing you can do to be ADA compliant is to make your website accessible to people with sensory disabilities like deafness or blindness. This includes alternate text for images and media that are more than decoration, like infographics and photos of things that explain or pertain to website content. This is most important if your website represents a public physical location, like a hotel or store of some kind. Because these lawsuits are usually pursued in the necessity, where people with disabilities really need access to such a business and can't obtain it.  https://www.ada.gov/

WEB DESIGN: For over twenty years, I have developed client sites for large and small businesses and in every sector imaginable. I develop responsive websites with WordPress which is the industry standard for website development. I specialize in Responsive Web Design so your website displays automatically on any device. Responsive design makes the most sense when developing your new business website because the design adjusts itself to the size of a user's screen. Your website visitors will be able to view all of your content on a desktop computer,...

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.

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.
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