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Legal Ops Hero: Jacqueline Cuevas

May 24, 2021 7 min read

Each month, we look forward to featuring members of the Ironclad community who are changing the legal industry for the better. This time, we’re excited to introduce you to Jacqueline Cuevas, Legal Operations Manager at Fivetran.

As the first hire under Fivetran’s GC, Jacqueline is helping build the legal team from the ground up in a thoughtful, strategic way. Her energy comes from thinking about the operationally excellent future version of the team she is part of, and in setting up the building blocks to get there. She is a proud Filipina-American and Bay Area native who loves puzzles, building, and creativity. 

Thanks for joining us for a Q&A, Jacqueline!

You skipped the typical law firm to pursue an in-house path. How did you work your way into legal?

So, I did intend to go to law school for a time, and I first entered the legal space with that in mind. I started out in contracts administration and just naturally (read: “really couldn’t help myself”) started organizing and implementing processes almost immediately.

As for starting in-house, at first, I wasn’t trying to make any distinction between in-house or not. At the time, I decided that I wanted to commit my next job to a certain kind of company (consumer finance education or protection), which is what landed me in-house.

When did you realize, “Hey, legal ops is a thing?”

I actually can’t quite remember the moment! Honestly, it really could’ve been a Google search. My earliest memory of legal ops is of a time when I was debating between training up as a contracts manager or exploring legal operations.

Also, it could’ve been when I first learned about CLOC. One of my co-workers (Hi, Vidya!) introduced me to her legal ops friend, Stephanie Lamoureaux (now leading legal ops at Square), who proceeded to energetically share her experiences with me and recommend that I check out CLOC. I’ll always think of those two people as really opening up the world of legal ops for me.

You’ve worked at some great brands like Credit Karma. What did you learn from that experience?

So much! Credit Karma was truly a wonderful place to grow my career for 5 years. I guess if I were to choose a few things…

  • There will always be risks, so we just have to make decisions about the risks we want to take or take steps to reduce them. This one comes to mind because I was recently reflecting on how it also impacted my personal life. Susannah Wright, the Chief Legal Officer at Credit Karma, always reminded our team and the rest of the business of that. 
  • Configuration > customization with technology—within reason. I know there are differing opinions on this, and I recognize that customization can actually be a big driver for progressing legal technology to the future state that we, as an industry, need. But I think I’m talking more about customization that isn’t keeping the broader future in mind. There’s a lot more meeting in the middle that can still be done between technology, operations, and lawyers, to deal with the fact that while technology evolution is fast, it is still not *that* fast.
  • Everyone is a legal ops client/customer. 
  • Despite all the reading we have to do, a legal team can still be the loudest and most energetic team on the office floor. (I genuinely say this with a ton of love!)

At Ironclad, our GC decided to make his first hire a legal ops role because he recognized that he wanted systems and processes in place before expanding legal. On the other hand, some companies hire corporate counsel first. What’s your thought on hiring for legal ops? Should it be a first key hire, or can it wait? 

I’ll use my favorite lawyer catchphrase: It depends.

In a perfect world where every GC or first legal leader is thinking far in advance on how to build a world-class legal business function, I would say ”100%.” But some people may not be thinking about that or have other immediate priorities, for differing reasons, and there’s only so much a legal ops person can do to help change their perspective.

I generally still wish for those folks to hire early for legal ops anyway, but you know, we’re now at this point where more people have a deeper appreciation and understanding of what legal ops brings to the table. I’d rather our folks go where we’re wanted and where we can be utilized in the best ways, rather than beating our heads against walls of resistance, disinterest, or misunderstanding.

We deserve better than that, especially if we plan to stick around for more than a year or two—which, I’d take a guess to say, is most of us because it often takes more than a year to build something really good.

What does your first 30-, 60-, 90- days look like as a legal operations manager?

My manager, Megan Niedermeyer, has done a fantastic job of (1) holding the line for me to take time to ramp up, and (2) setting a really simple but real 30/60/90 day framework of “Learn/Lean/Lead.”

I did get a fair amount of time to onboard (and in many ways am still doing so), but of course, the amount of work and my eagerness to get going have already put me in the middle or at the front of several initiatives—and I’m still in my 6th week! It doesn’t even feel like it’s been only a month and a half.

What skills does it take to be successful in legal operations? 

  • Flexibility was the first thing that came to mind. We have got to be SO flexible and so agile to get things done and to bring people along. Be ready to pivot always. 
  • Resilience and thoughtfulness in striving to maintain a balance between solving for the future and for now. 
  • The drive and ability to continuously (but efficiently) seek to learn across a broad range of subjects. For example, I never imagined I would learn so much about either accounting or marketing, ha!
  • Creativity. We can also think of this as resourcefulness, innovation, imagination, etc. It is the combination of knowledge and imagination that gives us the means to drive this industry towards a future it hasn’t yet experienced. 
  • The ability to foresee, elicit, communicate, balance, and synthesize multiple perspectives, to support our many internal clients (from Legal to cross-functional partners). Maybe we call this multi-dimensional thinking?

How are you adjusting to remote work? Any tips or tricks to balancing personal and work-life balance now more than ever?

I’m one of those who is thriving with remote work. No commute, no problem. Roll out of bed 10 minutes before my first meeting? Don’t mind if I do.

The main tip I would share is to give yourself a break! Or probably several breaks. If you need to, schedule it into your calendar! Just walk away from the desk and take a breath. Ask yourself, “Is anyone’s life at stake if I just pause for a few minutes?” If the answer is no, you have little to no excuse. If the answer is yes, thank you so much for what you are doing!

How do you drive adoption of the various tools in your tech stack?

I always start from the end-user and try to understand not just the concerns and needs they themselves vocalize but the world that they live in day-to-day. I have that “understand the whole to understand the piece” mentality because I often think that there are more intricacies or connections than people realize or than what may first come to mind when looking at just the piece.

Once I start tapping into that directly and talking with folks about the tool in the broader context, it helps me to understand even better where people are at, which in turn allows me to help people feel more like the tool is being designed to serve them AND the bigger picture. And it’s not just important to me to understand where they’re at in the process or whatever, but also emotionally and mentally.

For example, the first time I introduced Jira for internal task/project management, I was getting a lot of resistance in ways that didn’t totally make sense to me. I ended up doing 1:1 interviews with everyone to understand their individual worlds, how the tool would fit in, and what was challenging. Somewhere in the middle of that was a light bulb moment—one of the attorneys mentioned that folks were asking about the expected level of detail in using the tool because they were comparing it to billable hours.

As someone who hadn’t worked at a law firm before and hadn’t actually heard a lot about billable hours up to that point, it suddenly made sense why people were nervous. In this example, the “whole” wasn’t some larger system, but the whole person—the whole of experiences that came with each person. In the next team meeting, once I started framing it as more of a “to-do list” type of thing, I could literally feel the tension and nervousness dissipate.

What would you tell your 25-year-old self?

Be confident, your thoughts matter, and people who choose not to listen to you are missing out. There are folks out there who recognize that individuals can bring so much value beyond (or despite) age, title, years in the field, or lack of certifications.

Where would we find you outside of work?

At home, most of the time right now. I probably need more vitamin D.

Do you have any hobbies or secret talents?

I like to say that the four key components of my life, past and present, are theater, competitive team dance, board games, and legal operations. I have never gone a year without doing some type of performing arts activity.

Do you have a mentor or mentor someone? What advice do you have to find one?

I’ve been privileged to have several mentor figures in my life, and not just from legal but from other areas/industries as well. I would offer the thought that you can find a mentor anywhere—they don’t have to be in the same career trajectory to have valuable insights for you to grow from.

Also, I think people don’t flat-out ask, “Would you be open and willing to mentoring me?” enough. Sure, it could be awkward. But I think most people would be flattered and super ready to share their wisdom.

What book would we find on your nightstand right now? 

Multipliers by Liz Wiseman. It’s about how to amplify the smarts and capabilities of those around you. I’m only a few chapters in, but I love it so far. It unpacks the kind of leadership and nurturing that I’ve been continuously striving for, so I’m eager and hopeful to be able to apply the learnings in my daily life.

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Vera Devera leads Ironclad’s event programs. She’s passionate about creating extraordinary, one-of-kind experiences, and loves bringing people together. Connect with her on LinkedIn.

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