Step 2) Let them promise your software does whatever it takes to make the sale
Step 3) Make software do that
Step 4) Repeat
Step 5) Profit
I know it sounds crazy but I have worked at a couple software companies in the specialized enterprise space (things like healthcare IT) where software costs several hundred thousand per location and this is simply how it is done. The expectation is some very broadly featured software that you will customize to their needs and support. The upside, the expect to pay handsomely to license it, they expect to pay for the customization and expect to pay annually for support.
The key is a great sales person which often means you need to give them a hefty commission.
1) Craigslist? Where can I find someone who's willing to work purely on commission for a software product he's never heard of before?
2) So basically make the sales guy rack up the dollar amount by promising the universe.
3) Hire guys and project manage.
4) Love to repeat but where to get the next lead or client?
5) Profit, what to charge the enterprise guys? Is $500,000 a good starting point? Is it even possible to pull, one sale, one year, $500,000, that's me having to sell $49/month to a 1000 customers by the end of the year. I think the one client paying $500,000 sounds like a much better deal.
The salesperson does not really rack up the dollar amount on a feature by feature basis. There is not some line item set of features each with a price. They are buying the whole thing - the feature dance is all about ensuring the customer (whether you have the goods or not) that your package will fit their needs. Large corporations have evolved themselves into a potpurri of rules and processes for how they do things. They dont make sense in most cases which is what prevents them from using a low barrier to entry tool like something a small startup might make - basically, they cannot change their process to fit the software, they need the software to fit them. None will, I repeat, no software from any vendor will fit their business...the salesperson has to convince them that you are the best company to make it fit.
Preferably dont hire guys and manage, hire no one and do it yourself. When you are working way too much, have not enough time and a mountain of work ahead AND signed deals with customers (including checks) then hire someone. Repeat this process. DO NOT HIRE people until you absolutely need them.
If the sales person is any good, he had the next lead before he left the last meeting. When you find a good one you will have to tell them to slow down.
Pricing is a black art, too low and no one takes you serious, too high and you become a budget item that needs to be planned for and the sales cycle goes on for over a year which gives competitors more chances. Feel out your customer, ask them directly what their budget is...but mostly let your sales person worry about that.
The real question is do you have anything built yet? Do you have domain expertise in the space you are targeting?
In lots of cases enterprise software for niche scenarios is born out of a consulting engagement: Company A contracts you to build them a system for tracking widgets. You do so and get their permission to use that software in other projects. Company B wants widget shipment calculation software so you go to them and say 'I know about widgets, we built this widget tracking thing and we can add shipment calculation to it'. That is how the ball gets rolling.
Most software in this kind of space is packed full of features and rules that are not easily just spawned out of thin air - it usually takes many man years of development.
I have some stuff built and I have very good knowledge in this area I'm pursuing. There are some existing enterprise guys like kapowsoftware.com that I'm trying to emulate.
Good sales people are always on the lookout for the next thing they can sell. Snare their attention by being something they can sell. How you do that is up to you, but good content about interesting markets with lots of upside always gets my attention.
1. Determine what domain you want to focus on.
2. Understand the pain points of enterprise customers in that domain. Understand what competitors are doing. Immerse your self in that domain. Trade magazines, events, user groups, forums, competitors literature, corporate and influencers' blogs. Hangout where enterprise customers hang out in that domain.
3. Start forming opinions and start sharing through blogs, events, article writing, and speaking and interacting with industry influencers.
4. Based on the pain points you find out, narrow down to the ones you want to focus on. Start focusing on those pain points in your communications, become an authority on identifying and recommending suggestions to address them.
5. Develop a very basic MVP style product with minimal essential features that addresses the pain point area you own.
6. Keep doing #4 publicly. In one-on-one conversation with enterprise customers (avoid competitors and channels at this point) start dropping hints that you are working on a solution and looking for enterprise customers to be alpha/beta partner.
7. Give access to the interested people, communicate frequently, address the feedback and keep building.
8. Ask the enthusiastic ones for becoming reference and deploying in their organization at very low cost and as proof of concept. Focus on 1 or 2 beta testers, amaze them, get them to deploy your product, issue you a PO.
9. Write white paper and collateral resources on different solutions and configurations used by beta customers. Get some testimonials.
10. Start dropping hints about the customers doing beta test to generate interest and buzz. Get more people to start trying your product.
11. Rinse and repeat.