This Chicago startup makes hiring a corporate lawyer more like hailing an Uber

by Andreas Rekdal
January 22, 2016

As anyone who’s ever seen a courtroom drama knows, legal arguments can be won or lost over the tiniest of details. But while books and movies often portray these details as emerging out of serendipity or sudden epiphany, reality is far less glamorous.

To find the “smoking gun” that will swing a court decision in their favor, law firms typically crowd lawyers by the dozen into big rooms and task them with poring over thousands upon thousands of documents. Between the distractions that come along with working in a crowded room and the monotony of reviewing documents for weeks on end, this process can be absolutely terrible for productivity.

, a Chicago-based tech company that came out of stealth mode in October, is looking to bring the most expensive and time-consuming part of litigation into the 21st century.

By utilizing machine learning algorithms to supervise lawyers who review documents from their home- or remote offices, the company helps litigators save money by increasing productivity and cutting down on overhead costs. Esquify’s software automatically tracks when lawyers are actually working on the case, ensuring that each billable hour is at least 90 percent efficient.

Reviewing lawyers are rated for both efficiency and quality of work. Reviewers who do well are rewarded with more work and increased hourly rates.

“I was amazed at how completely devoid this area was of tech,” said co-founder Drew Stern (pictured above).

Stern is a Chicago tech veteran, with former roles including VP and director positions at

and Marketing Cloud, respectively. His co-CEO Scott Stuart, a former senior attorney at the Department of Justice with extensive experience from the world of private litigation, brings legal gravitas to the team.

In addition to the aforementioned efficiency gains, Esquify increases transparency by providing real-time analytics on progress and costs to date, as well as accurate estimates for when the project will be completed, and at what price. That way, clients can ratchet up the speed of the review by adding more lawyers as deadlines draw closer.

“The added benefit — as one attorney actually said to me — was, ‘I slept better at night, knowing that I can check in and see the progress of the review, and know how the review is going,’” said Stuart (pictured right).

While working under such close supervision might seem a little offputting to some, the founders said the feedback they’ve been getting from reviewers — all attorneys with bar certification in the United States — thus far has been great. Reviewers enjoy not having to commute to busy city centers, or spend hours filling in time sheets. One early reviewer — a stay-at-home dad whose wife is a partner at a major law firm — cited being able to adapt his schedule to pick his children up from school as a major advantage.

The idea for the company came over a dinner conversation between Stuart and Stern about how broken the current document review process is. After 18 months of building the company in secret, they launched in October last year and have been doubling the company’s customer base month-over-month since then. Just this month, the 14 member team expects to add another four employees.

With a recent $500,000 angel round of funding, the company has a big pipeline and plans to expand aggressively. And thanks to the popularity of the service among reviewers — thus far 100 percent of reviewers have taken on a second case — the founders are hoping to continue growing its reviewer community organically.

Images via Esquify.

Do you know of any Chicago tech companies we should be covering? Send us an email at [email protected].


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