Ironclad's new GC on career changes and how AI will make lawyers better

Taking time off from the business world can be career-clarifying. Jasmine Singh learned this after giving up her career as a commercial litigator at a large law firm to work as an instructor in the fitness industry for a year.

“The peloton behind me isn’t just a towel rack,” she joked in a recent video call with Legal Dive. Singh's need for a break to care for her health helps prioritize goals, she said, and shows the importance of choosing a job that aligns with personal passions in life.

Singh, former general counsel at software company Binti and deputy general counsel at Patreon, Joining a contract management software company Iron armored in November, where she leads a six-person legal team. She offers potential clients her experience implementing CLM software in a legal department, having been involved in four implementation cycles prior to joining Ironclad.

Editor's Note: This interview has been edited for clarity and brevity.

LEGAL DIVING: What are some of your short-term priorities as GC of Ironclad?

JASMINE SINGH: First and foremost is my team, who ensure we are well positioned internally across compliance, risk, regulatory and legal, and that we support the business to properly mitigate risk and maximize value through our contracts. Another important priority is to ensure that we develop products that actually best serve lawyers and our client base. So [that means] My team is beta testers for all the features we launch.

It sounds like you want to become an Ironclad power user?

The other day I asked my legal department to assign me an NDA in Ironclad for review because I wanted to know how the assignment process works, how the AI ​​tools in the system would work, how the approvals are routed, etc. Messages I received on the subject of signature wanted – all that stuff. So, yes, absolutely, I believe everyone on my team needs to use the product, including me.

Does your job involve not only legal work, but also speaking to customers and potential customers and helping to advance products?

Yes, and I actually really enjoyed it. The reason I'm talking to them is because I've done this four times now and I've made so many mistakes. I also did some things right, but I also did some things wrong. And so it's nice for me to go to other CLOs or GCs and say, “Hey, when I implemented it this way, it didn't really work for me.” So if you think about it, here's the lesson that I learned.

What was your job as a litigator and what prompted you to switch to the world of corporate law?

I have mainly conducted complex commercial disputes. It really ran the gamut: commercial disputes, professional negligence, insolvency. I misused trade secrets. Honestly, if someone was arguing about something, I was caught up in it. The internal transition was a truly unique story for me, also because I found myself in burnt-out law firms. I had a hard time breaking into companies where I felt like there was a mismatch between what I was doing in my personal life and what I was doing in my professional life. I always felt this tension. Therefore, my path internally was not easy.

I took a break, and it was a pretty sharp break. I stopped practicing law and became a spin lecturer for about a year. In telling my story, it was really important for me not to lose sight of how valuable my days as a spin instructor were. It was the place where I expressed my desire to ensure that I remained goal-oriented in my work. I have to take a lot of care about work. My personal and professional mission must align. I also have to be really excited about the people I work with. So when I went into entrepreneurship, I was committed to finding companies where I was fulfilling my mission and where I felt like I could be myself and really talk about the fact that I had all these other interests outside of the legal practice I wanted to pursue.

What advice would you give to someone in a company considering an internal move? Any tips or strategies for this transition?

I think it's important to have as many informational interviews as possible with internal employees to understand what day-to-day work is like, especially if you come from a larger corporate environment where there is a very clear division of labor. Internal departments just don't work that way. You have to do a lot of things that you don't really feel comfortable with. You have to figure out problems that you may not know the answers to. You have to be business-minded and focused on the company's goals. Anyone thinking about the transition should definitely talk to people in the company because you don't want to find yourself in a situation where you think, “Oh, I just made a mistake.”

For example, where are the two assistants I had at my old company?

It won't just be like that. Once you've made the decision, there's a multi-step approach. Know your story, be able to explain how and why you could be an asset internally no matter what practice group you come from, and use your network to connect with people in the industries or companies you need because I think it makes a difference when you try to find jobs that are good for you and not just any internal job.

How do you think about the optimal size of your team versus what legal work should be done outside and how to balance your outside spending with finding more budget for a larger team?

The really cool thing about this is that I can use Ironclad as the basis for this analysis. If I know how many contracts each of my commercial attorneys is reviewing and what their increase is from the previous quarter, then I know my sales team's contract pipeline that will come in next quarter. Then I can assume that by this time next year I will have double the number of contracts. And if I don't have a scaling plan built into my tools, such as more self-service on contracts, I need to gradually increase my headcount by X amount or X percent. So I really think about where the company is going and how that impacts how I think about my own resource needs. Sometimes it is an additional headcount, but not always.

Do you use external companies?

We generally rely on external lawyers when we need specific support on a complex legal issue. So if I don't have internal expertise on something or there's something that's more strictly regulated and you really need someone who's done it hundreds of times, that's when we turn to an outside consultant and that say, “Hey, you've probably done this for a lot more companies.” Can you tell us what you're seeing in the market, how we should think about it, and what the real risk is?

Is the lawyer inflation we hear so much about in moderation a talking point?

Law firms sometimes get a bad reputation because they just want to extend working hours. I think there are ways in-house lawyers can reduce the number of hours. We need to be specific about our request and say, 'I need you to do this specific project for me, and I only have so much available. Can you do it?' Sometimes an outside attorney would tell me, “No, I can’t do that for that amount because blah, blah, blah.” And then it’s my decision. How urgently do I need this firm's advice if I know my analysis risk-reward ratio?

Does your comfort level increase or decrease as you as a GC think about risk across your organization and more legal work from your department and firms is handled with AI?

A human should always be involved in the verification loop. The AI ​​tool is only as good as the human using it and the human reviewing the results. For example, if a work product is hallucinated and cites cases that do not exist or cites holdings that are not correct, a person still needs to verify these things and ensure that what the AI ​​has produced is complete and can and should be submitted become. And if not, it's up to them to revise it. I think the real risk is making sure that people don't assume that AI alone is the be-all and end-all. Sometimes you hear, “Can’t AI just do what the lawyer does?” That’s not possible, but AI can make the lawyer’s job easier and make the day go much more smoothly.

Do you think legal documents in general will improve as AI tools become more refined?

People are getting better at using AI and that will help the work product get better. AI will help people better manage their legal practices. And by that I mean people won't spend as much time and effort on routine, repeatable work. They'll be able to spend their money doing version 1 with AI and then do the next level of work, which is: Is this true? Is that correct? And be creative as a practicing lawyer. I can tell you, sometimes the hardest part of my job is putting something on a piece of paper. And sometimes I just want to get a piece of paper that I can mark. It really was a differentiating factor. I was a solo GC for a short time and did everything myself. Sometimes I just wanted a tool that would allow me to create a first draft that I could then work on.

This raises the question: Will there be fewer jobs for lawyers in 20 years than there are today?

I don't think there will be fewer jobs. I think there will be different jobs. Lawyers will continue to use AI to advance the profession and do less administrative work and repetitive tasks. You will continue to do future-oriented work and spend less time doing it. Lawyers still work long hours. And I think that AI will not completely eliminate more work. It will simply help them work fewer hours and really focus those hours on the work they find most interesting.