Cool, congratulations!! 1) For existing software a total rewrite is extremely risky and will most likely fail or cost significantly more than you are prepared

Cool, congratulations!! 1) For existing software a total rewrite is extremely risky and will most likely fail or cost significantly more than you are prepared to spend. Rewrite portions of it instead and modularize it. 2) The biggest problem you have is that large companies have very different needs than small companies. As a small company you simply cant have both. Enterprise clients need things done exactly how they need them done. Small clients dont want to pay for features they dont need. 3) marketing generates leads - you may not have a sales problem it may be a marketing problem. Do you go to shows? Mailing list? advertising? etc You have a sales problem if you are not able to convert leads to sales. 4) I sell exclusively to fortune 1000 clients and I can tell you they are a pain in the ass and will suck your morale dry. We recently have gotten two mid market companies (500M revenue) and they are simply a pleasure to work with. The elephants are great because they can dependably generate > 2M in business for us each year, but they will steal your soul. 5) 80% of your revenue in a single client is probably the single biggest risk you have. You need to get under 25%. --------- We do strategic planning each year and we decide on the major initiatives based on that. It goes something like this ---> What are the biggest business objectives for the company -->what are the problems keeping us from achieving those -->what are the specific changes we need to implement --> how do we tell if we were successful? In your case it might look something like 80% of or revenue comes from a single client (huge red flag)-> what is preventing us from increasing our revenue? Above you had said a few different things as being possible problems. You may want it to be that the code is bad, but if that really isnt the issue, then fixing the code wont get you more revenue. I think it is probably a lack of understanding of who your customer really is and what they need. Once you decide, then you can implement specific changes to make it happen. Those changes most likely will include determining how to reach those people then running campaigns to reach them. Once you reach them you can find out why they arent buying, then you can begin making changes to the code.