Welcome to our latest episode of Legal.io Community Spotlight, a series in which we highlight the careers and experiences of some of the most impressive legal and legal operations professionals working in-house.

In this episode, we explore the career journey of An Trotter, Senior Director of Operations, Office of General Counsel at Hearst and a Hearst Lab Scout. An is also the creator of Ops in a Box, Legal Edition – A magical kit to help those new to legal ops jump start their journey.

An talks about how she grew up in a family of lawyers and worked with the Rockefeller Foundation, Viacom, HARMAN International, before moving to Hearst Labs. Pieter and An cover:

• An's career journey to date
• Key responsibilities in her role as Sr. Director of Operations
• Key challenges and lessons learned in all her different roles
• The importance of understanding the culture of your legal department and aligning on goals

Pieter Gunst

Hey everyone!  My name is Pieter Gunst, and today I'm excited to shine a spotlight on An Trotter, the Senior Director of Operations at the American multinational media conglomerate - Hearst. If you hear weird, vintage telephone noises in the background, this is a parrot called Stubby. Don't be concerned. We're going to dive right in. So An, you're a problem-solver with a business and an operations background. And a really storied track record with organizations like the Rockefeller Foundation, Viacom, HARMAN International, and now Hearst. It's such an amazing journey, and I really want to hear from you. What's been your path to becoming the Sr. Director of Operations at Hearst? What's the journey bringing you here today?

An Trotter

Well, first, Pieter, thank you for having me today. I'm really glad to be here. 

My journey started with my dad, who's a corporate securities attorney, and was among the first to teach on the business of law at Emory Law School. I grew up with lawyers, and the business of law was the dinner conversation around our table. At the time, I was on a really different career path, and I came to New York in Arts Administration. And then, as you mentioned, I moved into fellowships management at the Institute of International Education and the Rockefeller Foundation. At the Rockefeller Foundation, I was named the Project Manager for the Senior Vice President's office, and that sparked an interest in going to business school.

So I went to business school at night while working during the day. And when I got my degree, I thought, "If I'm going to try corporate, this would be a good time to do so". And I thought back to those dinner table conversations and what my dad had said, which is that “Legal operations professionals were going to transform the legal industry right into the 21st century”.

Pieter Gunst

What year are we talking here?

An Trotter

This is in the 1990s [when] he was telling me this.

Pieter Gunst

That's early to the game. 

An Trotter

Yes. - I took that advice and I brought it back to the forefront of my mind, and I networked my way into a job at Viacom - which was my first legal operations position. I was working for Mike Fricklas, who was the GC, and Mark Morril, who was the Deputy General Counsel, and they were very forward-thinking. I helped them jump start the legal operation at Viacom. 

Pieter Gunst

Amazing. Taking you from Viacom to Hearst and being in this [Sr.] Director of Operations position, you're managing multi-million dollar budgets, complex operations. What are some of the key responsibilities that inform your day to day work? What does a typical day look like for you?

An Trotter

Well, first, I'd like to mention that every legal operations job I've had, has had a different emphasis. So Viacom, the emphasis was finance. At Harman, it was compliance. And at Hearst, it's been technology. But a common theme across all three of those has been process optimization. So thinking about "How can you get the lawyers to work at the top of their practice and take the ministerial work off their plate?" And also, "How do you cultivate an operations mindset in the organization as a whole so that you're not working alone, but you're working with the team to get that done?"

Pieter Gunst

What does it mean to have an operations mindset?

An Trotter

An operations mindset means to be thinking through who the resource should be to do a particular task, and how can it be done most efficiently for the desired end result for the client. And so that's what we're trying to think about instead of "What is the way I was trained to do this?", "How have I been doing this for years, that I am most comfortable doing it?", but "How can I take what I know and deliver it perhaps in a new way that will lead to greater optimization and perhaps client satisfaction?’ There's a lot of design thinking, user experience design, process-mapping involved in the thinking process.

Pieter Gunst

Right. So in your current role, because you talk about this evolution there was really a different focus between them. You say that you very much focus on technology and we'll talk about Hearst Labs doing very interesting work in technology in a bit, but the day to day is really pushing large-scale processing improvements that are largely driven by technology?

An Trotter

Largely, because Hearst was a little late to the party, right? I joined Hearst in 2017 as their first Legal Operations Professional, and all legal operations positions had now been in place for 20 years, so they had a lot of catch up to do. They had a document management system, but they were still processing their invoices manually. They had a very dated corporate secretarial system. So there was a lot of thinking in the beginning of: "What tool set do we need to take our agenda forward?". We now have most of those tools in place, so the conversation has shifted to: "How do we enhance our work processes? How do we work with what we have to advance further beyond what was our initial five year roadmap?".

And to that end, yeah, we just finished our strategic planning exercises and are in the process of reviewing that with senior management for the next 2-3 years.

Pieter Gunst

Right. I will not ask you to give away any company secrets, but I am very interested in knowing when running this kind of scale of projects; what are some of the key challenges (or maybe one key challenge) that you encountered along the way? What did you learn from it as well?

An Trotter

I think the key challenge at any organization is understanding the culture of your department, and helping them see a vision of what the future look of the department is going to be and communicating that to them so that you're working together. And that's hard. It's particularly hard because legal operations professionals tend to be planners, whereas lawyers tend to test very high in urgency and lower in planning. So it's two very different ways of working, and you have to reconcile those.

And then you have to win their hearts and minds to get them to work with you in partnership to move the agenda forward. And every place I've been, that's been the key challenge to master, and I don't know whether I can say I've come to the solution, because it's always hard, but I think that you have to communicate clearly and transparently. I think it's good to draw from the well of legal operations professionals who are in the trenches with you. It's a very warm and open and supportive environment. And by seeking out advice and listening to what those who've come before you have done makes the job a lot easier to manage.

If you know what your weaknesses are, and you compensate for those by surrounding yourself with people who have those [as] strengths, it helps you to maintain perspective and to take different approaches with your clientele. And in my experience, when you do that, there's no failure except for running out of time. So as long as you have the time and you have the people to back you up, eventually you will meet with success on whatever project you take on. 

Pieter Gunst

Amazing, so you don't only have to be a business and operations wizard, but also a social influencer extraordinaire to get all the voices in the organization aligned. It's intriguing to talk about that kind of legal operations management for these tech projects. But I also want to quickly highlight another very exciting area that's legal technology and also broader technology-related, and that's the work you've been doing with Hearst Labs, which invests in many early stage companies and across a wide variety of goals, but also has legal tech as a particular focus area, or at least an area they've been involved in. What's been exciting, in Hearst's perspective, in technology today and what is your team looking at in that strategic roadmap?

An Trotter

Thank you for asking me about that, Pieter, because being a scout at Hearst is one of the favorite aspects of my job. I'm a scout for both Hearst Lab, which focuses on women-led technology, forward startups, and also for Level Up, which has a similar focus, but for black and Latino founders. And, as I'm sure you know, in the venture capital world, less than 3% of all capital goes to companies that are led by women or people of color. So Hearst Lab and Level Up have both capitalized on the undervalued companies in the market.

Hearst Labs was started by our CLO, Eve Burton, seven years ago to both advance the visibility of women founders, but also of women executives at Hearst. And to elevate our innovation and to deliver value to the company. We've made 60 investments over the past seven years, and the current valuation is over $2 billion.

Pieter Gunst

That’s such an amazing number. And this also shows this is about also making a business case and finding those founders that do not fit the traditional mold and that are just, for that reason, an asymmetric investment.

An Trotter

Exactly. And you were talking about what our legal technology investments have been. And of course, that's an area that's particularly exciting to me. And I know you're familiar with Priori Legal, founded by Basha Rubin and Mira Levitt, because you're in the competitive space with them. Luckily, there's room for multiple players and it's an exciting place to be, with plenty of room to explore and grow the legal marketplace for corporate legal departments.

But two you might not know of is we have a company called Support Pay, which is working to facilitate payments between divorced parents, particularly when there is a court order involved, and meeting the documentation requirements for the courts and maintaining those agreements. And we also have an investment in People Clerk, which is helping people who are self-representing in small claims court to organize the paperwork and present the correct substance so that they win their case. I've been involved with all three and both in scouting them, but also in helping them with their product development, UX design and marketing plans. It's a lot of fun. I really enjoy that part of my job.

Pieter Gunst

That's such an exciting area as well to be investing resources in. I think from the future of legal work, where we're seeing entirely new work models arising in any industry. But for that to happen in one of the most traditional industries is very cool. I'm grateful that there's organizations like yours that are supporting founders in that work, because it's certainly is a rising tide. And then to also see these investments in companies that frankly, from a venture capital perspective, aren’t obvious. I think it's hard to justify consumer-facing legal tech as something that makes for that high-growth, unicorn investor thesis. 

And to see that that important area is being addressed; that we see, for example, optimization in the courts processes with preparation for a divorce, is tremendous. And then to hear on top of that that the ROI is there is just delightful. I'd love a chance to continue chatting about that. And maybe we should set up a separate conversation to go a bit more in detail. But I just think it illustrates the important work you're doing and also the many angles that you have on your environment and how you're able to apply your lessons from Hearst Lab and your work today and make that really have an impact on the department as a whole.

An Trotter

That's what drives both of us, isn't it? And it goes back to what my dad said, which is that, "There's an opportunity to transform how law is practiced in the 21st century, leveraging these new technologies’" So it's a very exciting time to be in the legal industry.

Pieter Gunst

What an exciting note to end this interview with - I couldn't agree more. There's never been a better time to be in legal technology, but there's still so, so much potential to improve legal operations and the system as a whole, as part of that.

An, thank you so much for sharing a bit of your journey with us. It was really a pleasure to have you here today.

An Trotter

Thank you for having me. I really appreciate it.

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