p.s. I said it wasn't easy, do I have any suggestions for selling to Enterprises where there may not be trust between the users of your product and their leadership?

Yes I do, here's one that is very well-suited to startups who want to sell to the enterprise: Product-Led Growth ("PLG"). This is defined as building a product and customer acquisition strategy around people trying the product for themselves and then buying the product without interacting with a human.

To make this work, you have to strategize which feature or features will close people using the product, as opposed to leaders looking at a PowerPoint with estimated ROI numbers. You have to make them discoverable, and you have to find a way to surface the value to users... In the product, not in a white paper or on a marketing web site.

You also have to have someone own PLG and ruthlessly experiment with user experience design and product design to drive better and better PLG. Yes, you have to track it and prioritize it.

PLG can't be your only strategy, you still need Enterprise Sales. For most enterprise products, PLG will never generate as much revenue as sales. It will be tempting to ditch it as wasteful compared to just building whatever the C-Suite demands from salespeople. BUT!

If you have any traction at all with PLG, your product will also be an easier enterprise sale. The problem the author listed is greatly mitigated by a product that has even modest success getting individuals and/or small businesses to buy it based on their trial experience only.

PLG can be the key to unlocking enterprise revenue, you just have to play the "long game" with PLG and treat it as a particularly honest way of obtaining user feedback, which must be coupled with a mechanism for improving the product based on that honest feedback: Someone must own PLG, must be held accountable for driving PLG, and they must have enough authority not to be swept aside by prioritizing top-down features.