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Stellar Women in e-Discovery: Terra Ickes [Podcast]

Mary Rechtoris

Described by her colleague as a “trailblazing pioneer,” Esquify’s Director of Operations Terra Ickes is a leader in the industry whose innovative spirit and dedication to customer success undoubtedly make her a “stellar woman.”  

During an interview for our Stellar Women in e-Discovery campaign, Terra spoke with us about the current state of artificial intelligence in the e-discovery field and why being successful—in tech and in life—means you have to be a little scrappy.

Terra Ickes

Director of Technology and Operations

“Terra works tirelessly to bring technology innovation to the Relativity ecosystem. As Esquify's director of technology and operations, Terra works with shared Esquify-Relativity customers to bring new technology innovation to review and has been integral to bringing our integrations, DocuTix and the Reviewer Command Center, to market. She manages our customers to success through an in-depth knowledge of technology, Relativity, e-discovery, and customer success. Her understanding of next gen technology, artificial intelligence, and analytics is inspiring. She's a trailblazing pioneer and is a standout leading woman in legal technology.”

– Drew Stern

Podcast Transcript

Mary Rechtoris: Hi listeners. I'm Mary Rechtoris, part of Relativity's community and customer advocacy team. This is Stellar Women in e-Discovery, a campaign we recently launched that encourages those in the e-discovery community to highlight stand-up professionals in the legal field. These are women who push boundaries, champion innovations, and pay it forward. Ultimately, they are women who inspire. Today we’re joined by one of our nominees, Terra Ickes. Terra, welcome and thanks for being here.

Terra Ickes: Thank you. It's a pleasure to be here, Mary.

MR: Terra, can you tell us about what drew you to Esquify and your current role?

TI: Certainly. I've known one of the co-founders, Drew Stern, for several years after we first worked together at another startup technology company here in Chicago called Sprout Social. We continued a professional relationship and friendship beyond that. Drew and Scott Stuart started Esquify as co-founders, and we remained connected. I started learning more and more about that business as well as the e-discovery landscape. As I learned more about Esquify, I was really drawn to their focus on the workforce management layer. What's really interesting about where e-discovery is now is that there's been a heavy investment and attention paid to the actual document portion of the review process and the adjacent technologies that may complement that e-discovery platform. But, there's been very little [attention] on the human review portion of that process, which is oftentimes the most costly. I was drawn to Esquify’s focus on the workforce and human review portion to optimize the communication, productivity, and overall quality of that part of the process. As Esquify continued to scale, there was an opportunity to join the team. As I'm sure you probably know, at startups, there is a melting pot of responsibilities that you hope new team members can take on. [My experience in] product management, operations, client services, and sales enablement training lent nicely based on what they were looking for in a new team member. Our relationship and their vision for the platform made the decision to join the team easy.

MR: I'm sure you wear many hats working at a startup.

TI: Absolutely.

MR: We had one of Terra's colleagues at Esquify nominate her for our campaign. I would like to read that nomination. “Terra works tirelessly to bring technology innovation to the Relativity ecosystem. As Esquify's director of technology and operations, Terra works with shared Esquify-Relativity customers to bring new technology innovation to review and has been integral to bringing our integrations, DocuTix and the Reviewer Command Center, to market. She manages our customers to success through an in-depth knowledge of technology, Relativity, e-discovery, and customer success. Her understanding of next gen technology, artificial intelligence, and analytics is inspiring. She's a trailblazing pioneer and is a standout leading woman in legal technology."

I want to give a bit of background for our listeners. Esquify is a legal technology startup that was established in 2014. Terra, I think you touched on this briefly, but can you tell us what has been the biggest challenge and the biggest reward about working at a startup?

TI: The challenges and rewards really go hand-in-hand. You have this great benefit [in startups] of not having the existing structure and approval processes that are often in place at larger organizations. With startups, you're making all those rules, which is really rewarding. But, it's also hard to do that. It's certainly an exceptional mental exercise to balance strategic prioritization of what you want to do with limited resources, and it requires accelerated decision making to choose the right things to focus on. So, the control and the ownership over those challenges are really fulfilling and rewarding. But of course, you certainly take on a lot of risk and there's no shortage of new, fun, challenging problems to solve.

MR: You mentioned you worked at Sprout Social and PowerReviews. What excites you about the tech industry?

TI: Companies in the tech industry, particularly startups, are usually born out of this idea or desire to make something that may already exist, in some form or certain way, better. You see this obviously in consumer rideshare services or companies that disrupt supply chains and go straight to market, including some of the mattress companies that I'm sure we've all heard of. In terms of my Chicago tech and startup experience, it has been exciting working with companies that strive to change the way businesses provided value to their customers—how they managed their social media presence with Sprout Social, and even user-generated content, which was my previous tech company, PowerReviews. With tech, there's always the opportunity to disrupt the status quo. Particularly with e-discovery, what's exciting about that portion or untapped area is it's really its own galaxy of big data that has seen remarkable growth and transformation in the past 15-ish years. But still, there are largely uncapped opportunities that exist for optimization. At Esquify, we think of that specifically in terms of productivity insights.

MR: Working at Sprout Social and at other startups that are outside of e-discovery, how do you think that better positioned you for working at a startup in the legal space?

TI: Regardless of the industry or vertical, there is the consistent need for accelerated decision making and ever-changing prioritization and problem-solving efforts and the context-switching that that comes with that and developing those muscles.

You’re also navigating uncharted territory and doing something that maybe no one's done before. Truly understanding the market and your potential customer use cases, and developing a product that solves that in the near term and the longer term, is extremely important and what makes a startup successful ultimately.

MR: Specifically in e-discovery, what do you do to keep on top of the market trends to stay in the know?

TI: At Esquify, we put a lot of focus on our relationship with Relativity as a larger partner and staying up to date from a development perspective on what Relativity is bringing to the market. Also, it's important for us to understand who else is in their development partner landscape and how we fit into that bigger picture to solve unique problems and needs, and ultimately win over and keep customers long term.

MR: Your colleague said that you're helping to drive a lot of the AI research and development at Esquify. How do you see analytics and AI impacting the e-discovery field and where do you see the greatest opportunities?

TI: I think there is a misconception as to near-term capabilities within the e-discovery space. That misconception generally applies to AI in other industries, in that it is perceived as something of a magic formula and pretty soon we won't need humans to do anything. Well, that isn't necessarily unrealistic very long-term with regard to specific industries. For AI specifically, what we have seen applied via machine learning in e-discovery shows us that AI still has a long way to go when it comes to the diversity of intelligence. With machine learning, we have seen the greatest successes so far in performing specific tasks that are able to be learned and mastered from distinct examples and patterns—and those [learnings] improve as the data set becomes larger. But, if we think about document review as an example, you don't necessarily have true patterns across a set of documents that may be involved in a litigation case. It's [AI] not necessarily applicable with a strong or high certainty of accuracy yet. Again, there are certainly great opportunities for that in the future. More in the near term is augmentation of tools that already exist, like predictive coding or TAR and other kinds of adjacent, third-party tools that can help humans make decisions better and faster.

MR: Going off that idea that AI has a long way to go, what are some factors that slow adoption, or what's driving some hesitation towards utilizing AI tools?

TI: With any new technology, it's really important for the adopter, so let's say the end customer like a firm, to understand how the implementation of a new tool will create value and what results they can expect.

Also, [they should] be armed to educate their team on the value, sell that internally, and then understand how to implement it and get buy-in from all of the folks that need to be involved within their organization. To cap that off, they also need to then get full adoption from the organization to actually execute and see that value.

It's a combination of those things from Esquify's perspective. We certainly see that with customers and part of our approach when we look to onboard someone is to push that whole concept of people-process-technology, so that they do see the value that we present to the market as being delivered through the platform.

MR: Your colleague said that you work hand-in-hand with shared Esquify-Relativity customers to bring new technology innovation to review. What do you find is the number one quality that customers look for in new technology?

TI: Especially with new technology, customers want a clear, understandable differentiating value. This includes from a technical and feature perspective—including how the tech actually provides value, and a confidence and understanding of implementation and adoption. How will you help them and support them in fully implementing the program and seeing it through to success? That's the piece that's really hard for a company to take on—you must help them understand exactly the best practices for successful program execution. It's that total value that a new customer must understand—through both of those angles, along with a measurable change and improvement as to how they execute and optimize their internal processes and activities that ultimately generates revenue, or in some cases, reduce costs.

MR: Thanks for the insight there Terra. As someone who looks to bring innovation into the space, what advice would you give to those looking to innovate in the e-discovery field?

TI: Developing a strong knowledge of Relativity and the other e-discovery platforms out there is a must, including the overall partner ecosystem. Also, it’s important to have an in-depth understanding of the market and how to uniquely solve or reduce a problem that is worthy of the buyer’s investment of time and resources to actually implement. Those are the big things to consider when you decide to invest or innovate in the field. Firms are slower to adopt change even though most say, “hey, we want innovation and we want change.” There are a lot of internal [factors], whether it be red tape or change management that have to happen, and that’s to adopt an existing technology. For a product that’s new to the market, it’s a an unknown technology that they've never used, so focusing on arming potential clients with the abilities from a people-process-technology perspective to create internal messaging, help them implement, and then focus on adoption to truly see that value.

MR: To wrap us up here: What has been the greatest piece of advice you've ever received?

TI: This advice was given to me more in the context of product management, but I really think that it generally applies to life as well. It is the idea of being okay with letting a lot of small fires burn around you, and not letting those distract you from an overarching goal and the larger, more strategic tasks that you should complete to get there. Letting those small fires burn, investing your time on the really impactful stuff, and focusing and prioritizing on what's the highest value in any given moment to execute with more of a long-term perspective. And, just being scrappy to get things done. I would say that’s been the best advice that I’ve received.

MR: I love that, “being scrappy.” Thanks so much for sharing your insight with us.

Terra: Of course, thank you so much for having me.

MR: Listeners, thanks for tuning in. For Stellar Women in e-Discovery, this is Mary Rechtoris, signing off.

Mary Rechtoris is a senior producer on the brand team at Relativity, where she's always collaborating and looking for new ways to develop and socialize stories.