One of the reasons why they have not done well is that the founders rarely have a technical background and the products are a torture to use. So, familiarity itself is not a problem.

The big issue is that the market needs to see tangible benefits without major turnaround times. That is impossible with even a relatively simple CRM/ERP product. It is hard (often impossible) sell to convince owners that it will take 3-months to complete the roll out.

The alternative is to no attempt a direct entry. Have a smaller product, or a modular feature in the main product, that they can use from day one and reap the benefits of. Get that buy-in and move laterally in pushing your main product.

Actually its not too difficult to convince SMEs that tech is the future. Most of them are willing to try new things and thanks to the prevalence of smartphones they understand a lot of the terminology.

What is difficult is to convince them that "your" tech is their answer. Though many of them are content with old school gadgets, they will shift once we showcase the advantages of adopting the cloud etc. In most cases, we get into an account by doing a proof of concept so that the businesses get the feel of the system before they buy.