Chances are that you’ve been reading up on, actively implementing, and/or already using tools and technologies to help you and your legal team work smarter and scale. The million dollar question moving forward will be “how do we build the right legal technology stack that’s right for us?” Natalie Kim, former Head of Commercial and Privacy Legal at Intrinsic, an Alphabet company, joins us to explore this question and delve deeper into the impact of AI as the legal tech stack evolves.

You have an extensive legal background, tell us a bit about yourself from a professional perspective. Why did you become a lawyer?

I’m drawn to problem-solving using interdisciplinary perspectives, and continuous learning. Practicing as a lawyer allows me to do both. In particular, with new technology where the law hasn’t “caught up yet”, how can innovators win in the market while doing right by their stakeholders? I’ve been exploring the answer to that question my entire career, first at Bay Area law firms representing technology companies (all the way from startups in the proverbial garage to the FAANG-sized companies) and then working in-house. I’ve managed billion-dollar deal desks for large established companies, and built contracting and privacy compliance programs from scratch for earlier-stage startups. What I enjoy about the journey is that legal advice is never cookie-cutter, and it’s more about getting to know your company and together building a custom solution tailored to their risk tolerance, industry vertical and other unique parameters. 

I’m also a systems thinker and a nerd about creating processes that are scalable and nimble. In my last role, I also managed the legal ops function, and there got to think in-depth about how to minimize the pain points in processes like the sales motion and privacy compliance. It’s amazing to experience this moment in legal tech where the annoyances we chalked up as part of being lawyers are finally being tackled in a serious way, and that makes me optimistic about legal tech as well as lawyering as a whole in the future.

How do you determine/measure success when counseling tech and AI companies?

Strength of cross-functional relationships - I really believe that lawyers are at their best when they have built trusted relationships with their clients and, when confronted with a problem, they’re thinking “let’s get legal looped in early” as opposed to trying to figure out ways to keep legal away. 

Another factor is the effectiveness of your legal operations (whether you have a formal legal ops team or not, you are still doing legal ops) and how seamless your legal processes are. How efficient are they? Is your team proactively taking steps to continuously improve and gauge colleagues’ sentiment about how well they’re working? The contracting process particularly comes to mind because every company has one and it touches nearly every team. It’s integral to the customer experience and how it affects the perception of your company as a result.

You’ve seen the idea of the “legal tech stack” change/evolve throughout your career. What are your thoughts on that emergence and how has it directly impacted you and your work?

When I started in my legal career, “legal tech stack” was basically just IT, and the extent of attorney involvement was mostly confined to using whatever software that was provided. The bleeding edge of digital transformation was still whether the process could be managed end-to-end using a computer as some attorneys still preferred to scan in manual markups. Every organization had its own set of tools, but I’m not sure if there was an expectation for them to play well together and lawyers had a mostly passive relationship with the tools they were being asked to use.

The current idea of a “legal tech stack” borrows from our engineering counterparts who try to build a “tech stack” that is efficient, plays well with adjacent components and is delightful to use. It comes from legal teams trying to reimagine the relationship they have with their tools as increasingly both the number and dependency on various software to execute legal tasks increase. Part of it is digitizing tasks that existed from time immemorial (like billing clients) but another part is utilizing new tasks that were previously unimaginable (like deriving real-time insights from a contract base of thousands). As the number of tasks and tools increase, it becomes much more important to make sure the tools are operating well with each other with intentional integrations that increase efficiencies as well as cost-effectiveness.

All of this takes a lot of work, doesn’t really sound like tasks lawyers traditionally do, but requires some depth of knowledge on legal work. This is where in the last decade or so, legal ops has grown out of this vacuum. We’re living through an evolution of this function from a pure legal support function to this combined chief-of-staff, COO type counterpart to the GC that handles not only an intentional development and curation of the legal tech stack, but budgeting, operational efficiencies and other special projects. I’m really excited about this development because it signifies maturation of legal teams as a department with serious focus on efficiency, enhanced client experience and cost effectiveness - all of which were traditionally gripes against the legal department. Coming back to the legal tech stack, these developments have transformed the lawyer’s relationship with the software to one that is more proactive - the best legal teams have an ongoing iterative development of the legal tech stack to accommodate changing needs within the team and asks from clients.

For any legal team, making legal tech stack decisions that are well-tailored for their specific needs should be a top-of-mind item. A commercial counsel might use the CLM every day and need it to work flawlessly with invoicing and billing tools, CRMs and e-signature integrations. A privacy counsel’s compliance dashboard might be linked to product documentation tools that product and eng teams use. These tools need to be integrated well in order to make the high-volume tasks seamless and continue executing without disruptions. A GC would want to work closely with legal ops to make sure that legal tech stack decisions are cost-optimized to defend budgets year to year. It impacts every team member and will only increase in importance as more tasks migrate online and are made possible with AI.

Do you see the modern legal tech stack changing in the near term because of AI? If so, how and when?

It’s easy to forget, since we’ve been talking about AI nonstop, that it’s still very early days with AI. I think there’s still a ton of low-hanging fruit that today is being handled with very manual, repetitive work that is contributing to attorney burnout and needless errors. We’re already seeing seismic shifts in how contracts are managed and negotiated, and within the next few years, those AI-first, early adopter legal teams will influence what will be considered best practices for legal teams as a whole. Zooming into one really specific problem as an example - today many teams still have a big word document (or worse, many fragments of word documents) as their contract playbook. Attorneys waste a lot of time trying to find it, update it and get the information they need. All that wasted time could be drastically reduced if it lived on one, evergreen platform. A good AI contracting tool can do that, while taking into account all of the forks that we care about (like custom provisions depending on geo). 

Another exciting area where AI is changing the game within legal is the “legal co-pilot” - lawyers are already using free options like ChatGPT extensively to get quick questions answered and/or “first stabs” of documents started. But, generic models are limited because they aren’t trained on legal-specific information for legal-specific purposes. Providers are starting to do just that, and are offering options where you can “teach” it the information about your company that results in fast tailored output. I’ve seen people have copilots do benchmarking or research projects where large amounts of information need to be digested and classified fast - essentially, something that would have taken an attorney a week can now be done within a few hours.

‍What are the longer term effects of AI in legal tech and the legal space in general?

Better minds than mine are pondering the answer to this question, but I’d be willing to guess AI is going to be neither all good nor all bad. In terms of “maybe bad” - as much as we gripe about it, part of legal training did come from all that monotonous, repetitive work they had us do as juniors. Reading voluminous material, summarizing said material, writing about that material. If AI is doing all of that for us, I’m not sure many up-and-coming lawyers will be incentivized to go the hard way in learning those skills. In 20 years, if an AI contracting tool had an outage, does that mean all contracting comes to a standstill because noone knows how to draft anymore? I hope not!

In terms of “maybe really good” - I think AI is an amazing teacher (when used right, for the right purposes). Today’s students can study much more efficiently (pre-2022 we had to read entire casebooks, or look up summaries online), and even practicing lawyers can ask AI all of the silly questions they’d be afraid to ask someone else. I still remember being a first-year associate wondering what an “indemnity” is - and now we can just ask ChatGPT to “explain it to me like I am a 7 year-old.” 

Who is Natalie Kim, the super mom and family-woman? What’s a day in your life like?

I mentioned I can do interdisciplinary problem-solving and continuous learning as a lawyer, and the same is equally true as a parent. I have 7 and 4 year old boys and a 19-month old girl at home so there’s a lot of code-switching, trying to tailor to different interests, languages, learning styles and capabilities. It’s the same muscle lawyers use all the time. I’m also training for the Seattle Half Marathon, and also have been volunteering as a board member at Cancer Lifeline, which is a Seattle-based nonprofit dedicated to providing better support to cancer patients.

What else is on your mind?

In June, I resigned from my job and started a sabbatical. My goals were to refuel my tank, reconnect with loved ones and recenter myself for my next adventure. Quitting with nothing lined up in a bad economy felt a little like jumping off a cliff, but it’s led to this incredibly serendipitous, rejuvenative period where I’ve been able to work on amazing projects (like authoring a white paper), advise innovative startups in the AI and legal tech space and most importantly, slow down and take stock of where I’ve been and where I’d like to go. I’m grateful for the many people who were willing to sit down with me and share their wisdom and career journeys, and it’s helped me change some of the less healthy habits I brought to work. If it’s a possibility financially, I’d highly recommend mindful breaks as it helps you stay replenished and can even create new perspectives, all of which can help you in and outside work.

‍Check out the the latest white paper from Natalie Kim - AI Contracting Tools: A Buyer’s Guide