I&#x27;ve been around the block in corporate. Here&#x27;s a guidebook (sorry I can&#x27;t spend more than 15 minutes on this)<p>1: Get insurance for your product. It will run really cheap for something low-risk like this. (Our firm pays less than 10 grand a year for General Liability, All-risk, <i>and</i> Professional Liability up to 10MM, which is more than good enough for nearly every company out there.)<p>2: Like Patrick said, the second you throw &quot;HIPAA&quot; compliance up there you have the ability to charge 10 (IME, more realistically, 25x -- but your expenditures increase as a result of that (incurred labor costs of additional support, etc)). At your 20 dollar price-point,  you&#x27;re undervaluing yourself by literally 3 or 4 orders of magnitude. Find an industry (say, that dude who mentioned oil, find out what regulatory institutions dominate), get vendor certified and insured and you&#x27;re looking at Oracle-esque money + 30% maintenance fees per year + support fees + modification fees.<p>Corporate sales is all about the steak and strippers (and nepotism) but it&#x27;s wildly lucrative, even now when oil is trading at like 40&#x2F;bbl due to SA flooding the hell out of the market. To put it in perspective, Parker hydraulic gear commands a 3 or 4x premium over other brands of nearly-comparable quality. It&#x27;s a lot like medicine or finance, huge markups but huge barriers to entry re: regulatory certs&#x2F;risks. I wouldn&#x27;t sell a site license for the product itself (per actual site, not per corporation, that midtown Manhattan office is billed separately from the LA office) for less than low 6 figures. (Sales cycles are long and expensive, your net on that will probably be 30%, which is why Oracle is always pushing for you to go buy that RAC license, it&#x27;s only 30% more!)<p>3: Along the veins of having industry compliance, obviously, offer support. Lets say you want to target the mid-market, Bob the engineer won&#x27;t be able to do buy the software until his manager sees a support contract available. You&#x27;re basically not going to maximize revenue targetting this demographic. Supports a must though. (Joel Spolsky factioned software sales off into the &quot;under 1k, petty cash&quot; and &quot;above 100k, gotta take it to the board&quot;. Supports a must for either one, at 400 a seat or 400&#x2F;k&#x2F;year&#x2F;seat) I&#x27;d target niche oil + board approval market with a relatively long sales cycle (especially if that other HN&#x27;er who mentioned oil can get you in for a round of golf with the CIO and give him the 30% rip or whatever&#x27;s standard now in enterprise sales).<p>4: Just a note, I take things apart for fun and your product isn&#x27;t well protected. I&#x27;m sure you know that since you left little fun notes around your code base (ps. I do snoop around, and I like you also! haha).<p>Just another why targeting the &quot;Oracle&quot; demographic (where they literally give copies away with no license keys or anything to everyone on their website), and corporations comply with the fee policies because it&#x27;s wiser to pay the fees now than have the BSA audit come in and have a 5x fine imposed.<p>---<p>I made a really long post about here[1] re: medical hardware (another tightly regulated industry with high margins and a sales team that makes or breaks) --  the relevant information is in the last few paragraphs.<p>There are also .NET licensing components if you make the (imo unwise) decision of targeting the mid-market, which uses USB keys + a network server to limit your trial functionality, but as I&#x27;m sure you know, the second those bits hit the hard-disk, someone like me is going to take Olly to it and have it smashed into pieces within a few hours to a few days. Those keys just keep the honest honest (i.e. a company might forget that their trial ran out, or the note to authorize the purchase didn&#x27;t make it down to their AR&#x2F;AP dept, etc).<p>[1] <a href="https:&#x2F;&#x2F;news.ycombinator.com&#x2F;item?id=11543670" rel="nofollow">https:&#x2F;&#x2F;news.ycombinator.com&#x2F;item?id=11543670</a>