UniCourt Influencer Q&A with Ivy Grey of WordRake
Storytelling is a critical component of any successful business in the legal industry, whether you are telling a story with data, visuals, or words. Using her background in journalism, marketing, law firms, and legal tech, Ivy Grey helps writers across the legal industry sharpen their stories in her role as Vice President of Strategy and Business Development of WordRake.
Ivy has an impressive legal career, having worked as a litigator and transactional attorney at Davis Wright Tremaine LLP, Togut Segal & Segal LLP, and Griffin Hamersky LLP, and she has been honored as a Fastcase 50 Honoree, ILTA Influential Women in Legal Tech, and ABA Women of Legal Tech, among other accolades.
We loved learning more about Ivy’s “accidental and indirect” path into legal tech, and hope you enjoy reading about her journey, the importance of writing in plain language, and how legal tech can best improve access to justice!
UniCourt: Tell us your story. What is your background, and what led you to what you are doing now?
Ivy Grey: My route to legal tech was accidental and indirect. I love words, story-telling, and creative problem-solving within constraints, but I never imagined those interests would lead me to a career in law or technology.
I grew up wanting to use stories to influence thinking and create cultural change. With those goals, I thought I was meant for a career as a journalist. Eventually I realized that I wasn’t content with telling stories—I wanted to be part of making them. That led me to a decade-long practice of corporate bankruptcy reorganizations and turnarounds. Bankruptcy reorganizations can be some of the most challenging and invigorating stories of change out there, and as the lawyer imagining and creating the future-state companies, you’re right at the heart of it all.
During practice, I also enjoyed reducing the mundane aspects of legal work using basic office technology. It met my need for creative problem-solving within constraints. But I didn’t realize specialized tools existed until I met PerfectIt founder Daniel Heuman who challenged me to test my proofreading skills against his software. I lost the challenge but won a new career path. I joined the PerfectIt team, then WordRake team mentored us as we moved into the legal space.
After that, I saw opportunity everywhere. Every time I faced a new problem, I looked for a way to address it long term. Any task that was tedious, repetitive, or ripe for human error was a candidate for a solution using tech. Over time, and with my sustained exuberance about improving legal writing through technology, the mentoring roles reversed and WordRake asked me to join the team. At WordRake, I get to be a subject matter expert, a solution designer, a storyteller, a problem-solver, and a techie. It’s the perfect combination of my skills and interests.
UC: What is WordRake? Can you explain what it does and what motivated you to take on the role of Vice President of Strategy and Business Development?
IG: WordRake is legal editing software that offers over 35,000 edits to improve clarity and brevity. In one click, it detects jargon and legalese, unnecessary modifiers, pointless introductions, nominalizations, redundancies, and more, and provides context-specific suggestions in the familiar track-changes style. It was designed for legal writers, so it will convert writing to plain English while respecting legally operative phrases and legal terms of art.
With past careers in journalism, marketing, and law, I know how much our words matter and how important it is to make sure our audience receives our intended message. It’s no surprise I would want to work for a legal editing software company that helps writers clarify and sharpen their message.
My role with WordRake is unique because I get to perform several internal functions throughout the company and work across teams, serving as a central hub to guide our strategy and make sure it connects with our users’ needs. It’s rare to have so much technology, law, and writing experience in one person and to get to use the full spectrum of my experience each day.
I also have an outward facing role, where I work with law firms to help them uncover their workflow and value problems with their current writing process and develop ways to improve the quality and efficiency of their written work. Every firm has its own approach to document creation and its own set of challenges. Though they have similarities, it’s my job to see every firm as distinct. With that understanding, we’ll imagine change together. WordRake can be a great, affordable way to improve writing, improve document workflows, and improve how everyone feels about the writing, editing, and feedback process.
UC: Tell us about your recent product release for WordRake. What new features are available and what challenges and use cases does it address for your clients?
IG: In October 2022, we released WordRake 4.0. Though we released many small updates along the way, version 4.0 was years in the making. We added a new editing mode, introduced seamless subscription purchasing, and refined and enhanced existing editing algorithms.
Now users can choose between Brevity mode and Simplicity mode. Earlier versions of WordRake offered clear and concise edits, which reduced word count, cut needless modifiers, converted nominalizations, and more. The newest version goes further by offering suggestions for improving readability and simplifying complex language, which helps writers comply with plain language guidelines.
Simplicity mode is important for lawyers because, since 2010, the Plain Writing Act has required federal government agencies, executive offices, and independent regulatory agencies to use “clear government communication that the public can understand and use.” The Act joins the list of over 775 plain language laws in the U.S. One of the most successfully enforced rules is the SEC’s Rule 421, which was introduced in 1998 and requires all prospectuses to be written in plain English.
Since plain language laws are gaining momentum globally and understandable written information is widely considered a civil right, it’s exciting to offer an editing tool to help writers reach those standards quickly.
UC: What are some of your top pieces of advice for lawyers and law students interested in working in legal tech?
IG: You can create your own path to success, so long as you are persistent and knowledgeable. What you’ve learned need not be formal, but it must be substantive.
You can break in and create opportunities by building connections and credibility. Write, blog, tweet, speak. Pick anything and use your voice. So long as you are knowledgeable or learning, your voice is worth hearing. While you’re building your connections, give first. Offer to help, share other people’s articles, publicly talk about legal tech you love, and support the community around you. Be meaningful and authentic with your engagement. It takes a while to gain traction, but it happens.
If you want to create technology, then you must have specific experience you can generalize to work for others, too. Examine what you know and what unique skills or approaches you have. Vet your ideas and study the graveyard of failed tech before you jump in with both feet. Find someone who will be your cheerleader and accountability buddy as you build. The rest will come if you have a good solution and you stick with it.
UC: How can legal tech be best used to improve access to justice? Are there any particular intersections between, legal tech, legal research, legal writing, and access to justice that stand out to you?
IG: Legal tech can improve access to justice in tangible ways. For example, legal writing technology can help clarify and simplify the language in forms, instructions, and notices so regular people understand their rights and responsibilities. This is what the plain language movement is all about.
When you understand your rights, you understand when things are unjust, not simply unfair—injustices can have legal remedies. Plus, many consumer protection laws or public benefit laws are meant for regular people to enforce or gain access to through forms. Clear writing makes that possible. And writing technology makes broad scale clarifying rewrites feasible.
That said, I think the biggest immediate way to improve access to justice is to meet people where they are, which means using communication by text message. Many people do not have access to a computer outside of work—or at all—but they have smart phones. Texting lets you communicate with clients on their own terms and their own time. And reminders from courts can help people show up for hearings, meet deadlines, and avoid follow-on troubles.
UC: What are some of your favorite sayings? What are some real-world examples of how you’ve seen those sayings come to life?
IG: “Don’t cling to a mistake just because you spent a lot of time making it.” — Aubrey De Grey
This is so important for lawyers because we are a profession ruled by fear of the unknown. For the most part, as lawyers, we would rather continue using the same broken processes to work than to try something new and imperfect. We are so afraid that we forget how change can lead to something much better. Unfortunately, the more we maintain the status quo, the less we want to break free from it.
I hope to see lawyers looking toward the future and seeing the hope and potential in new ways to work. This hope covers the range of things from how we create documents to how we regulate ourselves. We can be better and do more if we can see beyond the way it’s always been.
UC: What are your goals for 2023? What projects are you working on? Are there any events in the legal tech and legal innovation space we should know about?
IG: In 2023, I’m looking forward to continuing my focus on driving change through collaborations. I’ll start the year at the American Association of Law Schools conference in San Diego speaking about how law schools and vendors can partner to enhance technology skills and, in March, I’ll speak at the ABA TechShow about incorporating technology competence training through all stages of lawyer development.
These are continuations of the academic partnerships we first launched with Suffolk Law in 2019 and the Effectiveness Project collaboration with LTC4 and others to provide a best practices guide for document creation that launched in 2021. More collaborative projects will follow throughout the year.
UC: Where can we learn more about you and your work?
The Future of Lawyering Is Outside of the Box
Legal writing has been unquestionably changed by legal tech solutions like WordRake and advances in AI content generation tools like GTPChat that are still unfolding.
As we learned from Ivy, the future of lawyering requires thinking outside of the box and leaning into new technologies with the ability to improve not only our processes and end services, but also the way we effectively tell stories to our intended audiences in easy to understand, plain language.
We loved hearing from Ivy and are excited to see what the future has in store for her and WordRake!