I've been selling software to large enterprises for ten years. AMA!

Hey, great questions.

1. I think there are essentially two ways to validate product-market fit with enterprises:

• Many successful enterprise software companies I'm familiar with were founded by people who worked in large companies, observed a problem, and created a solution for it.
• Especially in recent years, we've seen a lot of bottom-up enterprise tools, e.g. Slack or Github, which were initially adopted by employees directly and then sold upwards to their companies.

For our own product, we've used a mix of these two. We built something we generally knew enterprises needed and then provided generous free tiers / cheap basic plans for individual enterprise employees to try our stuff. This provided the initial validation as well as valuable leads.

Then, we've scanned through the list of subscriber emails, filtered out all the gmails, hotmails etc. and looked for [email protected] ones. We've stalked their LinkedIn, analyzed their usage of our app, and reached out to them with very specific and customized offers to help and questions on how to improve. This had a very high response rate (>70%) and got us in touch with developers in the enterprise that already used our stuff.
From there, it was delicate. You can't be too pushy. You definitely can't be salesy. This is not the guy who'll pay for anything. But, as you keep providing value, you can ask questions about their usecase and requirements. I was always surprised how candid the answers were I got - less secrecy than I thought. Often, the initial dev will talk about your product within their team. They have a certain stake in its success - given that they're the ones who've discovered it. Once two or three use it, ask to talk to the next higher up about their long-term plans.

2. This answer follows on from question #1. I'll assume you have a product with a low-touch sales cloud version (e.g. free tier/< 20$/month base tier) and an enterprise version that is orders of magnitudes more expensive. If you have a pure enterprise product that requires a 6-7 figure initial investment, different rules apply. For that, you'd sell via your network, trade shows, and salespeople. But let's stick with the bottom-up model for the time being.

Most enterprise devs that pick up a 10$ / month tool are fairly unaware of their company's security and legal requirements. Once your tool's usage bubbles up to a higher level, someone recognizes that a) your product is used within their company and b) your "cheap" offering does not comply with any number of internal requirements.

This can be something like data-security policies (e.g. no data on third-party servers), SLA requirements, audit requirements, needed permission and access control structures, or any number of other policies this company has.
At this point, a higher-up manager or someone from procurement reaches out and inquires about your enterprise offering.

If your enterprise version ticks the required boxes, there is, in my experience, surprisingly little discussion about price (unless you charge something completely outrageous). The company needs it (as proven by the existing usage) and you can provide it in a manner compliant with their policies and processes. From here, it's a matter of navigating procurement (add 20% to the price, which you can knock of so procurement gets its bonus) and closing the deal. This usually involves any combination of the following steps:

• You send a license agreement over. (Get a lawyer to draft one or copy one from an existing product with a similar business model as yours - *although for legal reasons, I don't officially suggest that.)
• You get an altered license agreement back with completely unacceptable terms, e.g. holding you liable for any problem the company's IT faces for the next decade, whether related to you or not.
• You remove the worst bits, reach an agreement on the acceptable bits, and sent it back.
• You are asked to provide some context on your company and possibly some certifications (SOC-2 report, HIPAA compliance etc.).
• You refuse half of it. (trust me, this is fine. Almost no one ticks every box in the compliance lists - but keep the tonality around this friendly and cheerful.)
• You finally have an agreed license and enough checks. Procurement now goes off and finds someone who'll provide the budget and sign the deal.
  This can take ages, and quite a few deals are lost in this stage. Email your procurement person every few days and ask for updates/ offer help. Don't let off now. Potentially offer a 10% discount if it's signed before some date.
• You get the signed agreement. You countersign, mail a very hefty invoice, and open the champagne.