In this episode of GC Sidebar, Delida Costin, four-time General Counsel and Chief Legal Officer and now founder of Monarch Road Advisors, joins host Trista Engel for a candid conversation on the evolving role of the top legal seat and the mindset it takes to thrive there.
From Big Law beginnings to in-house leadership at CNET Networks and Pandora Media, Delida stepped into her first GC role at Pandora and went on to lead legal teams at Lynda.com/LinkedIn Learning, Grove Collaborative, and Group Black before launching Monarch Road.
Delida reflects on the accelerating forces reshaping legal, AI, quantum computing, and global regulatory complexity—and why GCs must move beyond gathering information to shaping action. She shares how founding her own firm early in her career sharpened her business instincts, ultimately connecting her to Pandora’s CEO and setting her on a path of entrepreneurial leadership.
Known for her philosophy of valuing “heartbeats as fiercely as dollars,” Delida also opens up about the importance of legal leaders claiming their place as true business executives, not just advisors.
Trista Engel:
Hi, I’m Trista Engel, CEO of Paragon Legal, and welcome to GC Sidebar, a short and sharp conversation series with today’s most forward-thinking general counsel. In just four questions, we cover the legal industry, leadership, careers, and a little fun.
Today I’m joined by Delida Costin, a four-time GC or CLO, and now founder of Monarch Road Advisors, helping legal leaders thrive in the C-suite and the boardroom. Delida began her legal career in big law before moving in-house with roles at CNET Networks and Pandora Media. She stepped into her first general counsel role at Pandora, and then went on to serve as GC at Lynda.com, which became LinkedIn Learning, and as Chief Legal Officer at Grove Collaborative and then Group Black. In Delida’s wonderful words, her philosophy centers on valuing heartbeats as fiercely as dollars.
Delida, you have been a long-time friend of Paragon, and I am so excited to have you here. Welcome.
Delida Costin:
Thank you so much, Trista. And if I could just say, I have been a long-time friend of Paragon, and it is so great to see this kind of series come to life and to be a part of it. I never would have imagined the growth that you all have had, and I’m happy to see it.
Trista Engel:
I love that. Thank you so much. Let’s jump in. What is the one biggest change in the last five to ten years that has impacted the legal department the most?
Delida Costin:
I feel like the one biggest change that has happened in the past five years that’s impacted the legal department the most is actually a series of changes that we can clump together. We spend a lot of time talking about AI and technology and legal tech, that’s just ubiquitous right now in our circles.
But some of the other changes that are really visible are the macroeconomic changes that are happening in our society. I feel as though they’re happening very quickly, they’re inputting a level of uncertainty into how businesses work. We can think about regulatory functions and regulatory schemes that are very, very complicated, and they’re different across borders.
There’s also, I believe, what the technology is bringing around is a change in where our resources are deployed. So it’s not going to be enough to spend hours doing diligence. We are going to have the capability to do some of that low-hanging fruit more quickly, and the skill set is going to become, what do you do with that information? There’s so much effort that’s taken in getting the information and pulling it together, and I believe that the legal function is going to have to become more adept at really having a point of view as to what happens as we analyze that data.
And I believe it’s only going to get quicker. We talk about AI, but quantum is on the horizon as well. Quantum is here, and I think that’s going to change the way we think, and business thinks, and the world thinks about so many different areas, and the role of the general counsel or the chief legal officer will evolve accordingly.
Trista Engel:
That’s a great insight. A few years ago it was all about legal tech, now it’s all about AI. No one’s even talking about quantum, but the trajectory of the change is just enormous. What accomplishment are you most proud of in your current role?
Delida Costin:
My current role right now at Monarch Road Advisors is to work with chief legal officers and GCs to, as you said, help them thrive in the C-suite and in the boardroom. And what I have really come to understand is that so many of us think of ourselves as partners to the business, or we run our functions in silos. But when you get to the top legal seat, you are actually a business leader. You are one of four, five, six people sitting around the table as executives figuring out the guidance of the business itself.
And so we have our teams that report into us, but we’re also part of a team that is driving forward and, hopefully, biased to action to deal with some of those uncertainties that we just talked about. And as a lawyer, our ability is to really take our seats there. One of the things that I’m most proud of is helping the people with whom I work do that. I’m really proud of the work that I did when I was still practicing to help my teams get there, but I love the work that I do now.
Trista Engel:
What’s one career moment that changed your trajectory?
Delida Costin:
In a lot of funny ways, I would say leaving CNET and starting my own little firm. I left CNET, I loved CNET, I thought it was great. Some of my favorite people still, in a lot of ways, come from CNET. But I left CNET because I was trying to figure out what else was out there in the world, and I didn’t at the time believe that I would be able to find it within the kind of corporate structure that I was in.
So I started my own law firm. I became an entrepreneur, I became a founder of something. And as part of that, I really had to start to wrestle with things like my own P&L, business development, marketing, operations. And I also wrote for a little online magazine called the SF Examiner, I think I wrote the “Starting Your Own Business” column. And that led to meeting the person who would become my CEO at Pandora, Joe Kennedy.
So in a lot of ways, stopping what I was doing and getting off a track, and learning how to survive on that new track, and keep building and growing and exploring and being curious and continuing to improve and learn, was the thing that really changed my career trajectory and enabled me to be able to move into the next phase of my career.
Trista Engel:
That’s amazing. That resonates with me personally in my own career, and with so many of the attorneys that work for Paragon, just stepping off that traditional path for a minute.
Delida Costin:
Yeah, sometimes we need to do that.
Trista Engel:
What’s something people watching might not know about you?
Delida Costin:
I think that the one thing people might not know about me is that I did not move to California to practice law, although that was an enabling move. There were jobs available at that time, everybody was looking for mid-level associates in big law. But I came out here to snowboard.
Trista Engel:
Okay, bonus question, who is your favorite fictional lawyer?
Delida Costin:
I wrote a post about this a couple of months ago, and it was a letter to Ally McBeal. Who remembers Ally McBeal? I loved her because she was on air at a time when I was a very, very young associate. And she was whimsical, the show was so whimsical, funny, strange, and at the same time she was kind of wrestling around the edges with some of the uncertainty that a lot of other junior lawyers were wrestling with. So Ally McBeal was it for me.
Trista Engel:
I love that. I read your post, and I encourage everybody to read it too. It mentions a lot of other wonderful fictional lawyers as well. Well, this was really fun, Delida. Thank you so much for sharing your journey and sharing your thoughtful answers.
Delida Costin:
Thank you so much for inviting me. It’s always a pleasure to be a part of the Paragon family.
Trista Engel:
All right, that’s a wrap on today’s episode of GC Sidebar. Catch more great conversations on our website at paragonlegal.com. Thanks for tuning in.
Prefer reading over watching? Below is the complete transcript from our GC Sidebar interview with Delida Costin Monarch Road Advisors, Pandora Founder and CEO, Former General Counsel
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