http://www.quora.com/Small-Businesses/Why-havent-we-seen-more-tech-companies-focus-on-small-mom-and-pop-businesses-especially-the-Enterprise-Software-sector
Most small mom and pops are complacent about their problems. They either don't realize a solution exists, aren't actively looking for solutions, or are content with their inefficient work-arounds. This means you have to seek them out and sell them directly, whether its by phone, email or walking into their business - some products require a combination of the three.
You have to charge enough to pay a sales person, reinvest in the company and probably pay your own (and any other founders) living expenses as well.
If you're bootstrapped its likely you can only afford to pay a small salary (usually not even that though) plus commission. This means you cant pay enough to attract talented sales people, so you either get the bottom of the barrel or you get someone inexperienced who will leave the second they find a job that will earn them more money.
If you are charging a one time fee, its extremely hard. A subscription service is much more doable. Even then, you have to be charging $xxx-$x,xxx/month - and unless its a SERIOUS pain point its likely the small business could/should/will spend their money more wisely somewhere else.
- I've started one b2b SaaS company targeting small businesses and worked at another in the same industry.
I saw the lack of focus ion this sector as an opportunity.
"We hire the best software developers in our community who are bored in their current jobs. We put them to work in partnerships with established businesses to co-create new product based businesses."
A lot of words there, could easily simplify.