General Counsels, Legal Ops, and CFOs - More Productive Conversations With Data

General Counsels and CFOs - More Productive Conversations with Data

Why are we spending so much in legal?

One SimpleLegal customer (public tech company with legal department that grew from a team of 1 to a team of 14) was told by his finance department that he "had the best system for tracking financials out of any department in the entire company."

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We are too small for ebilling

When talking to general counsels, legal ops teams and CFO's, I seem to hear this comment very often:

We are too small for ebilling.

Why? What does that even mean. To qualify it - I don't mean just the 10 person small business, I mean the companies that have 5, 10 even 50 legal team members, spending tens of millions annually on outside counsel and maybe even be part of a public company. Why would they feel they are too small for ebilling?

Maybe ebilling (and other tools for in-house counsel) are just for "the big guys", and everyone else has to settle for email and Excel. But that can't be it, we have ebilling in our personal lives. Our banks give us the ability to pay online. Many service providers will ebill us. Apps like Mint allow us to aggregate our personal finances into easy to use dashboards providing KPI's, trends, and actionable content. So why is it that a legal team is too small?

Because you are too small for them.

There it is. That's your answer. You aren't too small, you are simply too small for legacy vendors. Too small of an account, too demanding, not enough users, etc, etc. Too small for the pain it requires to roll out legacy software that can't scale.

Did you know, some companies will take 1 to 2 years to implement legacy ebilling solutions? That's not migrating from an existing product, that's starting with a clean slate. Shameless plug... under most circumstances, you will be up and running with SimpleLegal in less than 30 days (and we'll migrate you just as quickly). We implemented SimpleLegal at a multi-$B company with legal offices on 3 continents in less than 30 days. In their words, "we went from 0 to 60".

You're not too small to have data. You're just too small to line up IT, Finance, and Legal resources to work on a software implementation for the next 6-24 months.

As an integral part of your organization, you should have software doing as much of the administrative work as possible, so you can focus on what you are good at - protecting against risk, getting new customer deals signed, and helping grow your company - unless you really like chasing down accruals. 

One Question to Add to Your RFP: Are You the Future?

I'm lucky. I get to live in the future. I see self-driving cars every single day. 

We all live in the future in our personal lives. We can click a button to summon a car for a lift to a vacation home then click another button to get food delivered right to our door.

For companies, RFPs are all about the future. If your procurement department is going to the trouble of creating an RFP, you're probably buying a product (and a relationship) that you expect to use for the next 5-10 years.

And yet, every RFP I've ever seen only asks questions about what vendors can do today. It's time to ask your vendors to live in the future. I've helped write more than a few RFPs and I love the opportunity to help companies define their future.

If you're buying a product and a relationship that you expect to use for the next 5 to 10 years, it's important to know that a vendor will grow and evolve with your business.

Companies should add this one question to every RFP they issue: Are you The Future?

Are you The Future?

If you want more concrete questions (or you just don't want as many skeptical looks), try these instead:

  • What are your product's capabilities today that it did not have a year? Five years ago?
  • What are you doing today that you weren't doing five years ago?
  • What are you no longer doing today that you were doing five years ago? 

Too many vendors are doing basically the same things today that they were doing five years ago. They'll probably be doing the same things five years from now, too. Certainly, there will be new logos, new version numbers, and fresh proclamations about dynamic synergies in the cloud and on mobile. But not much will have actually changed and they certainly won't bring the future to your company.

In a world where "No one gets fired for buying X" it might feel safer to buy the past. But technology moves far too fast for that to be true for much longer. (Or maybe buying legacy is already no longer the safe choice.)

Companies that learn, innovate, and grow are shaping the future.

When you are evaluating vendors and their RFP responses and ask yourself: 

  • In 5 years, will their competitors be scrambling to catch up to them?
  • In 5 years, are my slower competitors going to scrambling to catch up to me and all the greatness that I'm buying today?
  • Are they the future?

Predictive Software for General Counsels

The $390M acquisition of RelateIQ has provoked some interesting commentary about making data useful.

The legal industry has historically been a late adopter of technology. A large part of a lawyer's job is to protect clients from risk. But, the legal world is rapidly catching up. Today, law firms risk being left behind by their peers and clients if they aren't able to take advantage of the data available to them.

In the legal world, "predictive coding" has in-house attorneys excited at the prospect of quantifying risk earlier in the lifecycle of a case. But the opportunities to capitalize on predictive analytics don't stop there.

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Exciting Times in Legal-Tech

It's an exciting time in legal technology.

New companies are creating modern, easy-to-use software for in-house legal teams. General Counsels have more choice and more control at lower prices than ever before.

At SimpleLegal, we've built a modern eBilling and Matter Management platform without all the overhead.

It's currently a field dominated by giants including Serengeti offered by Thomson Reuters, CounselLink offered by LexisNexis, and TeamConnect offered by Mitratech.

We have all the standard functionality: Accruals, Budgets, eBilling, Matter Management, Law Firm Ratings. But, we made it all easy to use, easy to scale, easy to implement, and easy to fit into shrinking budgets.

And we're winning!

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SimpleLegal Starter Edition

Until today, companies without an in-house legal team, were stuck dealing with PDF invoices. Company founders with access to World Cup stats on their wrist and fitness and diet data on their phones, have no data on the money they spend to protect their business, products, and employees.

Similarly, General Counsels at startups, having come from larger companies where they had access to data, suddenly find themselves re-typing invoices into Excel so they can have some basic information about cost.

The SimpleLegal Starter Edition helps these companies get data. SimpleLegal tracks invoices and provides intuitive, simple reports. Check out this 2-minute demo video to see how easy it is to get started.

Free for Most Companies

If you want to try it out, you can register for a 30-day free trial. After that, accounts are Free for the first user and first $250,000 in legal expense. Setup is incredibly easy. All you have to do is send a 3-sentence email to your law firm.

How a Law Firm Submits an Invoice Through SimpleLegal

Some of our customers and potential customers have asked how law firms submit invoices through SimpleLegal. They don't want a pile of PDFs dumped on them, but they want something easy for their law firm, too.

We created SimpleLegal to be Simple for clients and Simple for firms. Check out this 44 second demo video showing what happens when a law firm wants to submit an invoice.

Predictive Invoice Coding with Machine Learning

Predictive Coding

Predictive coding in the legal world usually means predicting the total cost of a matter or litigation. The idea is to use software to predict the likely end result ahead of time so that you can make better decisions.

Predictive Invoice Coding

Today, SimpleLegal is launching predictive coding for legal invoices. Early customers are seeing accuracy from our software of between 90%-97%. They are now review the results of our software and spend up to 90% less time coding invoices.

Ask any corporate lawyer and they'll tell you that they hate coding invoices. Legal invoices need all kinds of codes. UTBMS codes, task codes, project codes, customer codes, and cost codes.

Before SimpleLegal, invoices were printed out and so that codes could be handwritten line by line on the paper invoice. Then, the paper invoice was handed off to accounting to be re-typed into a spreadsheet and then entered into the payment system. It was a necessary but painful task.

Today, with SimpleLegal, invoice coding is primarily handled by software. The legal team no longer has to assign a code to each line. They only have to review the codes to verify that they are correct. We've reduced the time required to code an invoice by over 90%. More importantly, we've taken a task that no one likes, and we made software do it.

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OpenSSL Security Update for SimpleLegal

At SimpleLegal, we take data security very seriously. We're writing to let our customers and prospective customers know about our response to the very serious bug found in the widely used, OpenSSL encryption library.

There is no evidence that our servers were compromised and all usage fits existing patterns. However, the nature of this vulnerability is that it leaves no trace, so we are proceeding with caution.

First Step

When we were first notified of the bug, we took immediate steps to determine the extent of the problem and determine the necessary actions to safeguard our customers. Our application relies on the world-class security provided by to protect our data. We contacted their security team to confirm the necessary actions on our side.

How did SimpleLegal respond to the vulnerability?

First, we changed our server passwords and confirmed that the vulnerability was patched on the servers. Next, we updated our security certificates and updated our passwords again. Then we updated the login credentials of our accounts used to access Last, we terminated all user sessions for all customers requiring all users to login again to access their SimpleLegal dashboard.

How should I protect my account?

There is no action required on your side However, we do recommend all users change their password on their SimpleLegal account. You can reset your password here:

If you have any questions, please let us know at

Top 4 Reasons Companies Should Buy From Startups

Companies should actively seek to buy from startup vendors.

Large companies in particular do themselves a disservice by avoiding startups. Procurement departments often have vendor requirements that make selling to large companies a nearly impossible task for a startup.

Instead of de facto prohibitions on purchasing from startups, companies should actively seek out startups with innovative products and all-star teams.

Here are my top 4 reasons why you should actively seek out startups as vendors (as if those two weren't enough).

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