pg addresses this in http://www.paulgraham.com/start.html http://www.paulgraham.com/start.html Start by writing software for smaller companies, because it's ea

pg addresses this in http://www.paulgraham.com/start.html http://www.paulgraham.com/start.html Start by writing software for smaller companies, because it's easier to sell to them. It's worth so much to sell stuff to big companies that the people selling them the crap they currently use spend a lot of time and money to do it. And while you can outhack Oracle with one frontal lobe tied behind your back, you can't outsell an Oracle salesman. So if you want to win through better technology, aim at smaller customers. [...] Corollary: Avoid starting a startup to sell things to the biggest company of all, the government. Yes, there are lots of opportunities to sell them technology. But let someone else start those startups. On the other hand I see a lot of potential in selling cheap, lightweight, cloud-hosted, but effective "small business IT" applications on a subscription basis to help enable the little guys to compete with big business on a more level playing field. You're running a small business and you can't afford to shell out millions on an Oracle or SAP system? Maybe you can't afford to hire a full-time developer or even a consultant to build you an application? Who cares, when there's a just-as-good application that you can access online for less than $100/month? The key to this would be understanding the use cases particular to whatever industry you are selling to. You might have to have industry-specific modules within a larger application framework. Then there's always the potential challenge of ETL-ing the data from whatever legacy system the small business might be currently using in order to make it available inside your application, but that's much more of a consulting job than a product marketing job. That's got to be one of the the most expensive aspects of selling enterprise software in the first place. And of course, assuring the customer about security, privacy, and IP protection of their data would also be of paramount importance, if it's going to be cloud-based.