We're piloting now with a company with $1.1B/yr in legal bills. They're not so interested in the dashboard, but in access to our algorithms.
And yes, the existing products to review legal bills are crap (note: I'm waaaaay biased, obviously.)
Otherwise, I agree--going upmarket is their most likely pivot. They're also likely to switch to a %-saved fee model, which is what existing bill analysis companies already do, quite successfully. (SimpleLegal isn't the first company to tackle this problem, and it won't be the last.)
My advice to SL? Since they're clearly going the website-based growth route rather than the human interaction growth route, they need to work out partnerships with other legal tech providers, i.e., Clio and various legal app developers for iOS/Android.
Think of it this way: F500's also uniformly have IT departments staffed with highly-paid IT professionals. How good a job do you think most F500's do with IT cost management?
At the enterprise level, legal spend analysis is a huge deal, and yes the existing tools for electronic billing are really clunky (I work in this space).
%-saved is really hard to accurately calculate on a legal bill. Often inhouse counsel will negotiate a "discount" with an outside firm (yay savings!), but then that firm will overbill to make up the difference, and may do so in ways that aren't really detectable even by "machine learning". For example, they can pad their hours or add extra staff to the matter, or add some mysterious disbursements, or hell just raise their base rates next year to make up the difference. Who is to say that "REVIEW AND DISCUSS LEASE CONDITIONS AND DISCUSS SAME WITH CLIENT" should have taken 2 hours instead of 4? (A real example I just pulled from a real LEDES file).
I did a report for a F500 company a few years ago that showed that after the switch from paper to electronic billing, savings increased (in the form of discounts and auto-adjustments made by our rules engine), but overall spend increased anyway (in the form of increased fees and hours billed). So I'm not really sure that this is a problem that can be fixed by technology. People are gaming the system on both sides of the transaction.
I'd think that the general counsel of such a company is a prime target for this product. Carefully reviewing millions of dollars worth of charges billed six minutes at a time is extremely labor intensive. Having a product that does a first pass to find anomalies is a great way to cut down on the effort required.
But general counsel do want to keep overall legal spend under control, and are decision makers when it comes to purchasing several million dollars worth of legal software. For the purposes of closing enterprise sales, these are the guys you want to be taking out to fancy dinners.