GC Sidebar: Kevin Yung, General Counsel at MasterClass

In this GC Sidebar Season 2 episode, Paragon Legal CEO Trista Engel speaks with Kevin Yung, General Counsel at MasterClass, about building modern legal teams, scaling legal operations, and what today’s GC role really requires beyond practicing law.

Kevin shares how stepping into the general counsel role expanded his focus far beyond legal advice, requiring deeper involvement in operational strategy, legal technology, and team design. He discusses why modern GCs must think carefully about the systems, tools, and support structures that allow legal teams to scale effectively as businesses grow.

He also reflects on what makes a great legal hire in today’s environment, explaining why adaptability, growth potential, and flexibility often matter just as much as experience. Kevin explores how AI and legal technology can augment legal teams, where human judgment remains essential, and how flexible legal talent can help organizations navigate changing business demands while keeping lawyers focused on strategic work.

It’s a thoughtful conversation about leadership, hiring, legal operations, and the evolving role of in-house counsel.

Full episode now available.

Read the Full Conversation

Prefer reading over watching? Below is the complete transcript from our GC Sidebar interview with Kevin Yung, General Counsel at MasterClass.

Trista Engel:

Welcome to GC Sidebar, a short and sharp conversation series with leading general counsels about the decisions, the reflections, and the people behind the title.

I’m Trista Engel, CEO of Paragon Legal, and today I’m joined by Kevin Yung, General Counsel at MasterClass, the online video platform where the world’s most accomplished creators become teachers. Kevin has built his career where content, creators, and technology meet — from Vessel to Twitch, and now leading legal at MasterClass. Kevin, thank you so much for being here.

Kevin Yung:

Hi, happy to be here.

Trista Engel:

Alright, let’s dive in. What’s one issue facing legal teams right now that you think is overrated or premature?

Kevin Yung:

I’ll answer this in two ways. First, I think it’s premature that people believe AI is going to replace legal teams. But I also think it’s incredibly important for legal teams to focus on AI and become truly proficient in using it. Legal AI tools are great — they’re powerful augmenters for legal teams. But the fallacy right now — who knows where the technology will be in one, two, three years — is thinking it will entirely replace a legal team. I don’t think that’s true. There are a lot of potential weaknesses: it hallucinates, and it doesn’t have the institutional context or the relationships that legal teams build with the business. So it can’t fully replace a lawyer, whether junior, mid-level, or senior.

That said, it’s incredibly important for legal teams to understand how AI works, because it helps augment what you do day-to-day. It helps augment the advice you give, helps with research, helps you draft. Ignoring it would be akin to ignoring the development of the internet back in the day. So I don’t think it’s prudent for legal teams to ignore AI, but I do think it’s premature to believe it will entirely replace legal at this time. It’s a great tool, and I continue to think about how it will help my team support the business.

Trista Engel:

I 100% agree. We don’t want fear of AI to stop us from figuring out how to best use it and harness it, because there are so many valuable use cases, and we want to make sure that as an industry, we keep up and figure out how to best use it.

Kevin Yung:

It’s important too, because it’s not just legal tech AI — the business itself is using AI constantly. If you’re a product lawyer, your engineers are vibe coding constantly, so if you ignore AI, you’re not going to understand the product. It’s important to really understand how your business teams are using AI as well.

Trista Engel:

Great point. What’s something that surprised you about the GC role?

Kevin Yung:

The amount of non-legal work I do. Some parts of it I expected — the people management, the budget management, even being a strategic thought partner to the business, which I do day in, day out. But I didn’t expect to focus so much on the products and services my team uses to be efficient, good lawyers. That’s non-legal work in my view.

As the business scales, it’s hard for legal to get resourced one-to-one — we’re a cost center. If we double our business, I don’t suddenly get double the headcount. So thinking about legal tech, and the products and services that help me augment my team to continue supporting the business, is something I do daily and weekly. Legal tech has always been here, but in the past year or two there’s been a proliferation of legal tech development with AI. I’m constantly evaluating tools, taking calls, looking at new services and products that will help me augment my team. That’s something I never really thought about before taking on the GC role — being a product evaluator, taking sales calls with product teams. That’s new and different for me.

Trista Engel:

That’s a really interesting and nuanced point. It’s a common theme that being an individual contributor is very different from leading a function, and what got you to this role isn’t what will make you successful in it. You’ve pointed out some of the main differences around people management and budget management, but I like how you’ve highlighted the less obvious parts of the role — being a buyer is a really different skill set, even from being a leader.

Kevin Yung:

Yeah, absolutely.

Trista Engel:

What’s one career moment that changed your trajectory?

Kevin Yung:

I spent the first part of my career primarily as a securities and capital markets lawyer, in New York and San Francisco. A little over a decade ago, I got the opportunity to join a small startup — 50 to 70 people — focused on the media space. I was the second lawyer there, at a company called Vessel. At the time, I had no experience in the media or content space, and no real startup experience beyond being outside counsel. My boss’s boss at the time — my mentor and friend now — took a chance on me. He basically said, “If you were able to do an IPO and an M&A transaction, you can learn this, you can figure this out.”

That opportunity really changed the course of my career. I wouldn’t be where I am now without him taking a chance on me and hiring me. The lesson there, I think, is that you hire for the person, not just the résumé. Experience is incredibly important, obviously, but it shouldn’t be the only thing you judge someone on. You’re looking for someone who can be flexible, do multiple things, and learn quickly — especially for a small legal team like mine. I want jacks-of-all-trades who can learn things quickly, because we work in a startup environment. I want people to keep growing, evolving, and taking on new opportunities as the business changes. So it’s really important to hire the person, not just what they represent on paper.

Trista Engel:

I absolutely love that, and it’s a great lesson for any hiring manager or leader — that it came from someone taking a chance on you and seeing something in you. Hiring is the hardest and most important job any manager has. You’re hiring for potential, not just experience, and you articulated that very well.

Kevin Yung:

And beyond hiring, it’s also the ongoing mentorship. I love giving my team the ability to do different things. I’m constantly in conversation with each of them to make sure they like and enjoy what they’re doing, and that there are opportunities for them to try new things at the company. My legal team is very small, and our company moves quickly, as I’m sure you and your other clients experience. I want to give my team the opportunity to grow their careers, and I want to keep fostering that. So it’s not just hiring — it’s constant mentorship and evaluation.

Trista Engel:

Agreed, that’s fantastic. GCs today have a wide range of resourcing options beyond just FTEs and outside counsel. What’s your approach to resourcing your legal team?

Kevin Yung:

As I mentioned, scaling a legal team isn’t one-for-one with the business, unfortunately, since we’re a cost center. So beyond products and services that help augment my team, I continually think about more flexible legal arrangements — temporary arrangements, or hiring people through Paragon, which I’ve done historically. It helps a lot to augment my team.

I think about it in two ways. One is short-term engagements — for example, we’ve used Paragon to support our team during sales cycles. End of quarter, end of year, deal flow picks up, and since I have a pretty small legal team, I can bring in someone from Paragon. In that case, I look for someone who can ramp up quickly, understands the sales cycle and flow, and gets up to speed fast.

For medium- to longer-term arrangements, flexible staffing also works well, but I approach it like hiring — you want the right person, the right fit for the team, someone who understands the business and can take a longer ramp-up period. I’m okay taking a chance on somebody in that sense.

Trista Engel:

That’s great, and to tie it back to your earlier point — it’s part of developing your team. You can give them different opportunities and let them take on new projects if you bring in someone to cover the day-to-day. I love the framing — the two ways you think about flexible talent, both to augment your team and to develop it.

Kevin Yung:

Yeah, absolutely.

Trista Engel:

When you’re not lawyering, where are you most likely to be found?

Kevin Yung:

My mom is a librarian, so I grew up around books and love reading — probably curled up on a couch somewhere with a book. Typical Bay Area: I’m outside a lot, love the outdoors, love skiing, love hiking. Love traveling too, experiencing new cultures and new experiences.

Trista Engel:

Awesome. Any recent book recommendations?

Kevin Yung:

I’m a big sci-fi/fantasy geek, so I’m reading the last book in the Sun Eater series. For nonfiction, I’m reading a book my brother recommended called Proto, about the development of an ancient language and how it spread throughout the world. Very different books — one’s sci-fi, the other’s nonfiction.

Trista Engel:

Very cool, thanks. And the bonus question — Paragon turns 20 this year. What’s one memory from 20 years ago that still stands out to you?

Kevin Yung:

Twenty years ago, I was a 1L in law school at Cornell, in upstate New York — my undergrad was in San Diego. So 20 years ago, I was probably stuck in snow somewhere; it was the first time I’d lived somewhere with snow. The memory I remember is 20 inches of snow being dumped on us overnight, and I only had flip-flops and shorts. I didn’t understand what the snow was — it was a real shock to my system.

Trista Engel:

Straight to the mall to get the proper attire!

Awesome. Well, that was really fun, Kevin. Thank you so much for sharing your thoughts and your journey with us today.

Kevin Yung:

Absolutely. Thank you so much.

Trista Engel:

Alright, 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.