Having worked in the SMB segment with a variety of newspaper partners over the last six months or so, I thought I'd share some thoughts on what we've learned from the small & medium business "segment". I use air quotes for the "segment" because it is more like a catchall... a bargain bin at the grocery store where you're as likely to find onion powder as an overstock of mango chutney.
Lesson #1 - small and medium sized businesses really are not a "segment" but rather share the economic commonality of being more or less owner operated.
Many of these small businesses are successful outside of the context of the Internet. The business owner opens a retail store on the right corner. A restaurant has the best salsa in town. A plumber is on call all day, every day, and has a great reputation for providing excellent service even on holidays.
Lesson #2 - Internet marketing makes a lot of sense for small and medium businesses, but it isn't what built many surviving businesses. So it is a "nice to have" and not a "must have" for many established SMBs.
New businesses have a lot to gain by using social media and internet marketing as promotional vehicles. There's a reason mobile food trucks use Twitter aggressively. New businesses get a ton of response from things like Groupon. Awareness is the sweet spot for SMB internet marketing and social media today because the business owners are motivated.
Lesson #3 - Motivation matters, and it's a lot easier to sell an immediately effective solution to a needy customer.
Finally, simplicity and ease of use matter. For many SMB owner/managers, the ease of use bar is extremely high and probably beyond what most software people should expect. This brings me to an interesting point -- it is almost impossible to market "software" to local businesses. If you ask a SMB owner/manager what they want, odds are they won't tell you that they want "software".
As such, our business continues to evolve... smarter and more effective than ever.