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Esquify wins IE´s Legaltech Venture Day Chicago and moves to the final round in Madrid


Esquify, winner of the U.S. arm of the Global Legaltech Venture Days, bets on putting humans, not technology, at the center of its e-discovery management engine. Drew Stern, CEO and Founder of Esquify, shared his journey and views on the legaltech industry.

On June 15, Northwestern University’s Pritzker School of Law in Chicago hosted Legaltech Venture Day Chicago, a global startup competition organized by the Law Schools Global League and Ontier, in collaboration with IE and South Summit.

Esquify, winner of the US Leg, competed against five other finalists, all women-led companies, including deal management software Doxly (backed by Dentons’ Nextlaw Ventures and quite well known in the US), pro bono law platform Paladin, Bite Size Legal, Determinator and HAKA. Having such an excellent group of selected startups competing in this first Global Legaltech Venture Days is proof that legaltech entrepreneurs in the industry are focused on how they could help drive law forward through technology.

Esquify, along with Singapore Venture Day winner startup, EasyLaw, and the winner of the last arm of the global qualifying round that will take place in México on June 20 in collaboration with ITAM, will qualify for the final round in Madrid, which will be celebrated at the LSGL Annual Reunion on July 25.

During the final Venture Day, the three winning startups will pitch in front of investors, government officials and business pioneers in the hope of being selected to join a custom built incubator in Madrid to help further develop the product for the legal market.

Esquify´s reason for participating in the Global Legaltech Venture Days competition is that legal innovators globally have a shared investment in remote work.

“We built Esquify with one major assumption—e-discovery teams will continue to become more decentralized and that collaboration amongst team members will no longer be performed solely in-person, but will be done virtually either within the same office but on different floors, in different cities or even different countries,” Stern said.

“Being included amongst so many other thought-leaders and innovative founders was in inspiration. We are further excited by the opportunity to meet our international colleagues in Madrid later this summer” 


Congratulations on winning  Chicago Legaltech Venture Day! We are excited to have you in Madrid for the final round. Tell us about yourself, your professional journey and experience in the legaltech industry.

I’ve always been fascinated by the intersection of business and technology, particularly how technology can augment business professionals’ work and ease their pain points. To that end, my career has been focused on building innovative technology solutions and strategies as both an entrepreneur and intrapreneur at Salesforce, American Express, Buddy Media and Sprout Social. I built Esquify with my co-founder, who is an attorney, with the belief that we could take these same principles that work in other industries into the legal sector.  

Outside of business, I’m passionate about my family, travel, volunteering for human rights and LGBTQ organizations and my dog, Brooklyn, who comes with me to work (aka Esquify’s CCO Chief Cuddle Officer). 


Could you briefly describe what specific problem Esquify solves?

At Esquify, we are an AI-driven workforce management platform for law. We’re using cutting-edge, 21st-century technology to create a complete picture on what drives eDiscovery team management success.  Where most review team managers are pulling one-off spreadsheets and managing reviewers reactively, Esquify helps discovery teams proactively understand performance and provides real-time statistics without needing spreadsheets. We then make the data actionable via supervision, drill-down and communications tools built specifically for law. 

Our platform approach to team management takes analytics and project management to the next level, creating an accountability loop that drives both reviewer and manager success. Further, we help our clients tap into the ‘big data’ opportunity in eDiscovery by becoming a centralized repository for their review data, which usually isn’t saved at all today, whereby they can analyze past performance to create predictability on future matters. 


How did you come up with the idea?

My co-founder, Scott Stuart, Esq. and I came up with the idea of Esquify via real-life pain-points Scott witnessed in everyday practice. Scott had seen eDiscovery projects that were over budget, inefficient, had low accountability and were all-around-painful. What started out as a passing conversation over dinner took shape into creating a workforce management platform that could drive review team success. Thus, Esquify was born. 

“Being in law at this important inflection point in time, is incredibly exciting albeit challenging”


What was the greatest challenge you encountered?

An ongoing and consistent challenge is being a new technology in a legacy industry and selling into the legal community. Law in general lags behind other industries when it comes to adopting and embracing new technology- even when tech can ease their pain! We overcome this challenge by identifying the early adopters of new technology and showcasing how our technology can actually drive a competitive advantage for the firms and companies we work with.

Another challenge that I think all LegalTech start-ups encounter is access to capital. Since technology sales in law can be more challenging than in other industries, I find that traditional VCs have a tendency to shy away from law as an investment category even though there is so much opportunity for success.  We’ve been very fortunate to find a few VCs and strategic partners, like Relativity, that understand the space and believe in what we bring to the market. 


Do you feel lawyers/law firms are getting better at accepting and adapting to new technology?

Lawyers and firms are starting to become more accepting in the adoption of new technology. I think the use of technology in everyday life and the rise of millennials into law firm ranks are both helping shape new attitudes about using new tech in law. But its still a slow shift. Innovation is all about trying out new ideas, testing them, tweaking them and making them better. Often times, since lawyers tend to be more risk adverse, finding clients to be apart of that iterative process and ones that are willing to see the benefit of being early adopters can be challenging. 

At Esquify, we have taken an aggressive development and testing approach whereby we were able to shift that iterative process to our own teams and we launched with a fully realized platform. For example, we have run our own reviews, on our own technology and made improvements and new features based on our own observations. Taking on this effort has proved pivotal to our success with getting lawyers to adopt our new tech. 


What did you learn from working in the legal sector?

It’s incredibly invigorating and inspiring to be working within the legal space. As I mentioned above, I love solving real-world problems through technology and coming up with new, innovative solutions to do so. Law has many opportunities to innovate and being able to dive into an industry with outside vertical knowledge, along with a co-founder insider, allowed us to break the mold, take best practices from other industries and truly create cutting-edge legal tech. Being in law at this important inflection point in time, is incredibly exciting albeit challenging. 


Will we be seeing Esquify in different jurisdictions? What are Esquify´s next steps?

Absolutely. Esquify is already being used by global teams to manage a decentralized team structure in eDiscovery. You will see Esquify continue to bring our innovations to new jurisdictions as the challenges we’re facing in the US are ones other teams are facing all over the world.  As a cloud technology, we’re not limited in deploying our tech anywhere in the world and we are already seeing international firms tap into our solution to help solve their review team woes. Moreover, Esquify will continue to develop new, helpful technologies that further augment the power of the people tasked with review. 

Learn more about the Legaltech Venture Day México

Apply and register here!