Scaling Legal in Education: Elana Freeman of Swing Education

How do you scale legal and compliance in one of the most complex regulatory environments, without becoming the “no” department?

In this episode of CZ & Friends, Cecilia Ziniti sits down with Elana Freeman, Head of Legal & Compliance at Swing Education, to discuss what it takes to build a nimble, high-trust legal function inside a fast-growing EdTech marketplace.

Elana shares how she navigated multi-state compliance, employment law risk, COVID disruption, and AI adoption - while keeping legal efficient, business-aligned, and people-first. From showing up unannounced at a pension fund office to weighing 7x compliance risk against product innovation, this conversation is packed with practical insights for modern in-house leaders.

Follow Elana:

@Elana Freeman on LinkedIn

Show Notes:

• Elana’s journey from compliance manager to Head of Legal
• Scaling a two-sided EdTech marketplace across 7 states
• Managing employment law risk in California
• How COVID forced rapid product pivots
• Building trust across remote teams
• Creating efficient, lean legal operations
• Designing simple, practical AI policies
• Risk vs. reward decision-making frameworks
• Why legal leaders don’t need to “know everything”

Follow us on all social platforms to get each new episode when it drops.

⁠@Cecilia Ziniti⁠ on LinkedIn

⁠@CeciliaZin⁠ on Twitter/X

⁠@GC AI⁠ on LinkedIn

@gcai_co on X

⁠gc.ai⁠ website

Transcript

Elana Freeman 0:00

Illinois has this fund Chicago Teachers Pension Fund requirement for certain teachers where you have to contribute to this fund. And we were like, all right, fine, we'll contribute to this fund. But CTPF, as they call it, wasn't answering our calls, et cetera. So I just showed up at the building and I was like, hey, can I talk to your? I don't remember who what the title was. And they were like, yeah, sure. So I just got a meeting when they were just completely not answering our questions. It was great.

Cecilia Ziniti 0:28

Welcome back to CZ and Friends, where we talk with legal leaders, operators, and technologists shaping how modern companies work. I'm your host, Cecilia Ziniti. Today I'm joined by Elana Freeman, the head of legal and compliance at ed tech company Swing Education. She's built and scaled legal at a fast-growing ed tech company, operating in one of the messiest regulatory environments you can imagine. And I know because I was a GC of an education company. It's regulated by state. You're dealing with children, you're dealing with all kinds of issues across federal, state, local, and even municipal law. And she's done it with a people-first approach, obsessed with clarity and speed. What I love about Elana is that she doesn't make legal the loudest voice in the room. She builds trust, creates the conditions for good decision making, and helps teams move faster. All the good stuff we love about in-house counsel. So let's dive in. Elana, welcome to the show. So you've said something I like in your in your public post. You said great leadership is not about control, but it's more like how to create conditions so good decisions happen consistently and quickly. Unpack that a little bit.

Elana Freeman 1:37

Yeah, it's it's a lot of facets. I think one is building a great team. If I can be hands-on on every single decision, so my team needs to make good decisions and be equipped to do so quickly and effectively. And the other piece is trust, trust with your executive team, trust with the entire company. So I can say more about strategically how we do that, but that's a high level.

Cecilia Ziniti 2:00

Got it. So you joined Swing as a compliance manager and got promoted through to now you run legal. Did you use those techniques to do that? Or like, like, was this, did you come to this through experimentation? Like what does it mean? And then yeah, I'd absolutely love to dig a little further of like, okay, trust, everybody talks about trust. Give us an example and make it real for us.

Elana Freeman 2:21

Yeah. So I came, yes, I came in as a compliance manager. It was a mixture of legal compliance and business development. It was a small company at the time. I think I built trust because right, we were, we were in person. It was a 40-person company. We all knew each other. And I wasn't the legal person when I joined. So that trust was built organically. It wasn't intentional. And then over time, as my role grew, as a company grew, as we became remote fully, as we converted to an employment business model in California, and my role became legal, head of legal, et cetera, I realized that that trust that was so organic and easily built in the beginning wasn't necessarily coming through, right? If someone's hired remotely and then 10 and 20 people are hired remotely who don't know me, then you know, if someone's ahead of legal, you're you hear no, no matter what you say, no matter what the legal person says. So I realized, okay, this is not to be taken for granted. How do I build trust? And part of it was, and we can dive into this later, these legal team presentations with every single team across the company. I was like, we need to help them know who we are, chat with us, build trust that way, um, and bring them in on legal. So they actually understand the risks we're dealing with, that their team is dealing with and can issue spot on their own. And they don't feel like legal is just telling them no all the time. Part of those presentations also were to help it be very clear that we are a team. We are not telling you yes or no. We are working together. We know the risk. You know the business outcome, you know the what your team does best. So we need to work together to make sure we're mitigating appropriate risk. And some risk is really okay to be, you know, should let to let go. Um, we're a startup, right? We have a healthy risk tolerance. Those are a few ways, you know, we have office hours, we talk to people in layman's terms. We really try to not be a team that talks in legal lease and is just saying yes, no.

Cecilia Ziniti 4:17

So swing education's business model, uh, looking at your LinkedIn, you actually started in 2019. And swing education, it looks like it's software around connecting schools with substitute teachers. So this this feels like a like a like a law school hypo, but what's the like orienting us a little bit? What it what is the what are the core legal questions that you deal with? And it is the business model is is it like Uber where you're you got the contractors or orient us as though we're we're new product council starting on your team. You're gonna give us, you're gonna give us an overview of what's what's going on at your company. And then come with some real examples around that, around, around how you how do you educate the business on that too?

Elana Freeman 4:58

Yeah. So I highest risk legal stuff is probably employment and miscellaneous employment laws in California and misclassification in other states. The complicated piece about this is we're in seven states across the US. We have decided to operate two different business models. Some states we operate an independent contractor purely we're a platform, gig economy platform.

Cecilia Ziniti 5:22

So I am, you know, Sunnydale Elementary School and I need a substitute teacher. I go to Swing and it's it's like looking on LinkedIn. Or like what is the actual how does the product work?

Elana Freeman 5:33

So how does okay, so the product is basically as a sub, you set up, meaning you tell us, here's my credential, here's my background check. I'm okay to teach from a legal perspective. Once you give us that information, you're able to view requests that our school partners post on the platform. In California, you're an employee. We operate an employment business model in California. That's where the tricky compliance stuff comes in. And then as a school, you're like, I need a sub. Let me just quickly post it on the swing platform. And then it's automatically viewable by like, you know, hundreds of subs in your region to accept it and show up at your school.

Cecilia Ziniti 6:05

Got it. Okay.

Elana Freeman 6:06

Yeah.

Cecilia Ziniti 6:06

Yeah. I mean, I've used every, you know, I have kids and I've used every kind of childcare matching service in the books, right? So it's always interesting because you, you know, this two-sided marketplace, you got to worry about compliance on both sides, right? So um interesting. Okay. And then do you actually vet the teachers then for qualifications? So do you have to deal with certification compliance and and all that as well? Yep. Got it. Okay. All right. So when you joined in 2019, give us a from to journey. So you joined in 2019 and COVID hadn't happened yet, and you were a compliance manager. And so you were basically, it was mostly employment law at that time. So then what did you build and how did how did the company grow?

Elana Freeman 6:49

Yeah, it was actually, it wasn't necessarily employment, it was compliance, it was substitute teacher compliance requirements. So it's exactly the certifications, background checks, et cetera. They're different in every state. Some schools have their own separate requirements. It's actually really can get really complicated and it changes. So that was a primary role. It was that, and we were looking to develop a new market. So I opened up Illinois as a market. So it was let's make sure we're vetting new markets appropriately, as in taking into account the compliance piece, which was not a concerted effort, a concerted role before.

Cecilia Ziniti 7:23

So this is like bringing back my ed tech G C days. We had my team had a map that was like, how many states are we good in? It literally was like, I'm very visual, right? I measured in international relations. So I had at one point knew that knew the world map, but basically we had a map where it was like basically red, yellow, green of like, and some states, you know, it it is. I mean, education, of course, under the constitution, right, is a matter for the states. And so you get lots of different, lots of different requirements. Okay. So you come in and you're you're doing the compliance in the in the one state, and then you're like, all right, we're gonna open up Illinois. So that's a huge scale legal project. How did you, how did you do it? And any any fun stories along the way?

Elana Freeman 8:02

Life's such a fun story, actually. So, okay, we were in at the time six states, and we were opening the seventh in Illinois. So Illinois has a fun Chicago teachers pension fund requirement for certain teachers where you have to contribute to this fund. And we were like, all right, fine, we'll contribute to this fund. But CTPF, as they call it, wasn't answering our calls, et cetera. So I just showed up at the building and I was like, hey, can I talk to your? I don't remember who what the title was. And they were like, Yeah, sure. So I just got a meeting when they were just completely not answering our questions. It was great. Um, it turns out we didn't have to have to contribute to the fund. We can't logistically, but that was a great story. Just showing up in person.

Cecilia Ziniti 8:39

I think having a really calling is showing up in person, I think particularly it's like, you know, and we've we've talked about this theme on the podcast too of like regulators are humans too. You know, anybody that works at a court, any clerk of court, a judge, there's you know, this interesting research that, you know, judges give worse sentences on Monday mornings and any other time, you know, this kind of like that that people are humans. So you show, so you go, you go to the regulator and you do and it sounds like you got what you needed.

Elana Freeman 9:05

Yeah. It was like an it was like impromptu hour-long meeting without any reason for prescheduling or anything. It was great.

Cecilia Ziniti 9:13

So okay, so then so you launch Illinois, and how do you systematize that kind of compliance? Because I think that's something, especially in an AI world, that a lot of folks are thinking about. So, so tell us like, and then, you know, you mentioned ability trust. You said early it was easy, but then, you know, you do things like open up Illinois, brand new line of business, you know, at least one seventh of your of your company's revenue. I have to think you were in trust that way, right? So talk about both things. Talk about like what is the machine that you had to build, and then, and then how did um what was the business reception of that?

Elana Freeman 9:47

Yeah. So I mean, we were lucky that we had already had the infrastructure for the compliance piece because our product team has built on the back end sort of modules to take subs through. Like, here's where you put your certification, here's your background check module, et cetera. So I just had to really map it out and hand it to our product team to productize it. So that piece, we already had a skeletal infrastructure in place from California, et cetera, because they're similar. They're not the same requirements, but they're similar enough. Um, and we also have a sub-operations team, right? Who's looking into background checks and updating background checks? So that part was actually pretty easy. I'm I'm lucky in that, in that sense, that we're very product-centric. On building trust, I think, you know, it was organic and easy at the time. And everyone at the time and still knows that schools value compliance, right? Your reputation and client base is not gonna grow if you don't meet those compliance requirements. So from that respect, it's very aligned and easy. Then, you know, nowadays, like AI policies, for example, is like it's a different, there's a friction there between like our team wants to just use AI, but for everything. Right. And I'm like, okay, but there's some limitations here. How do we and that's maybe a little trickier? Um interesting.

Cecilia Ziniti 11:08

Well, so so you you hung it on something interesting, which is so your schools are your customers, um, and there is a whole class of companies. Um, like Vanta would be one of them, where you know, any any legal tech, but also, you know, Carta, which does equity management, Vanta, which does compliance for SOC2 for technology companies, where the product is really compliance. And in that scenario, Legal has this like extra special role. It sounds like it's sort of similar with you too, right? So a school is getting, when they, when they hire you or when they they go through your marketplace, they're getting the substitute, but they're getting the substitute that they know has been background checked, that they know has met the minimum, you know, master's degree or whatever it is that they need. How does the fact that your company sells compliance kind of it sounds like you think it makes your job easier? Any other impact that it has for you as a as a leader of a legal team?

Elana Freeman 12:06

I think, yeah, it makes my job a lot easier for that facet of legal and compliance for sure. Um, I think, I think you nailed it. It does for that. I mean, there's other facets, right, of legal compliance that is not as straightforward, but that piece is pretty aligned. And there's of course friction where ideally the minimum requirements possible increase the number of subs we have who are subsidy teachers who are vetted and ready to go. We also understand that that's not what our schools want. I'd say it's yeah, it makes my job relatively easy in that way. Amazing.

Cecilia Ziniti 12:40

Let's talk about COVID real quick. So it's been five years, but you know, is it fair to say your company came out stronger? What was the what was the process? I mean, did business stop completely for a while? But I have to imagine actually substitutes, you probably need more in COVID. So what was the what was the business impact? And then um let's talk about that first. What was it? What how how did how did that uh affect you as a leader company and then you as a leader?

Elana Freeman 13:07

Yeah, COVID, our I mean our business went to complete zero overnight because schools closed. So no one needed subsidy teachers and we had zero revenue. So that was rough. And as schools, you know, we that was interesting because we started, we spun off pods for a little while, right? When schools were closed, families were wanting teachers for their pod, if you remember this term during COVID.

Cecilia Ziniti 13:30

So that was kind of families as customers then.

Elana Freeman 13:35

Correct. So we would try to like white glove match really good substitute teachers with families. We looked into we looked into a bunch of stuff. We looked into tutoring, right? Remote tutoring options. None of those really panned out. So I think once schools came back on, it was like we need subs now. And we realized we needed to recruit quickly and we had we didn't have the supply needed. So that was a bit tricky. Um, but then after, you know, after that all balanced out, it was business as usual. I mean, schools had this COVID funding, which helped them get more subs. But it was a bit of a roller coaster until it all evened out for sure.

Cecilia Ziniti 14:15

Wow. So getting through that, and presumably now, so it sounds like your business is healthy now, six years later. Um any enduring lessons from that or relationships, you mentioned trust. Any anything that you can that that's coming to mind?

Elana Freeman 14:34

I think the ability to be nimble is really important in those types of scenarios. Like the pods thing didn't work out, however, we were able to get some revenue when we otherwise wouldn't, and we were able to just spin out this new product, like you know, overnight, basically. Um and that was a good learning from me. Um, I think yeah, I was like, we need to build terms of service, we need to build everything surrounding this new business. So I think the lessons there are how important it is to be nimble because things happen, right? And yeah, and the trust piece helped with that, right? We had a team that was like decently small who knew each other decently well. So we really all galvanized came together really easily to make that happen.

Cecilia Ziniti 15:18

You mentioned nimbleness. You've also talked in the past about building a lean, high-performing legal team. What does efficiency mean? And are there specific indicators where you're like, all right, we're getting bloated, we're, you know, we're moving too slow, we're not being nimble enough. And what how do you quash those instances?

Elana Freeman 15:36

Yeah. Yeah. I'm kind of obsessed with an efficient legal team. Um, so I think what efficiency means, it's not necessarily working quickly. I think from a, and this is of course from a startup perspective, understanding what are our highest risks that we really do need to dot our I's and cross our T's on, and what are the ones that are medium that we want to kind of mitigate, and what are the ones that are just not super risky and aren't worth the effort, and getting really being thoughtful and getting really clear on that. And that includes discussing and getting aligned in some instances with leadership, right? Like I mentioned, our AI policy, other ones are kind of just purely legal. But but yeah, and then making sure your team understands what those prior priorities are. What are things that are really higher risk, what are medium, what are low, so that they can execute against that and prioritize really effectively.

Cecilia Ziniti 16:34

So when people, when you come in as a boss and you're feeling that someone's not prioritizing, like let's get super breast taxed. Do you literally like have a list? Or like, you know, we had a situation in our company where basically somebody spent like two days rearranging folders and it was like, what is going on? And you know, and you kind of like see that and you're like, well, I mean, it's good that they're well arranged and and probably a nice end result. You know, it you almost wonder as a manager, like, you know, if the person derives joy from rearranging folders, like, you know, that's cool. But then you're like, well, you know, is that really the right priority? And and then, you know, there's there's been some uh leadership uh writing from Ben Horowitz where he literally he has a book called The Hard Thing About Hard Things, and he talks about being a CEO. And he says that he would kick off meetings, or if he saw this happening, he would literally say, that is not the effing priority. And it to him, it was important to actually use the F word to underscore, like it just isn't. And yeah, that's obviously an extreme version. But if you said, okay, you're obsessed with efficiency, you help the team with priorities. What do you do when you see it going wrong? And have you done it? Maybe give us some examples.

Elana Freeman 17:52

Yeah, okay. I have the I have two advantages here. One, we're a team of two. I have one direct report. Um, so we have the advantage of a really close working relationship. The way I do it with him, well, one, you know, we're lean, we don't have a lot of time. He needs to prioritize. Yep. Two is if he comes to me and he is like, here's this issue, I'm gonna like appeal it or do this thing or whatever. I consistently ask him when he brings projects to me, is this some version of, is this worth our time? What is the outcome we're getting from this project? And I do that across the board. Like when we talk about things, my main question is what is the goal and what is our outcome and what is the impact? So, me just asking those questions consistently throughout our working relationship means he is now asking the same questions and coming to me with the answers proactively, right? So he has already done this analysis in his head of what is the impact of this? Is it worth it?

Cecilia Ziniti 18:52

Have you tried this with your leadership team? Um, in the sense that, you know, as a general counsel, as a head of legal, you know, you you have maybe not as many direct reports, but arguably you're responsible for, you know, or you in name at least are responsible for compliance of, you know, the hundreds of employees and then, you know, potentially thousands of contractors and and you know, the the people that provide the swing service. So how do you, you know, when you've got, when you think something is going wrong, or you're in an executive meeting and you're like, oh God, I don't think that's a good idea. But put us in your shoes and what do you do?

Elana Freeman 19:28

I try to really bring translate the law into layman's terms and be presented as a bought partnership, like, hey, there's a legal flag there. I don't know if I would necessarily say it that way, right? But this is the risk posed, right? For example, and I'll give you a concrete example. In California, if we switch from weekly pay for employees, these are hourly, non-exempt. If we switch from weekly pay to daily pay, our potential liability goes up by 7x. Wow.

Cecilia Ziniti 20:02

Is this under PACA or what's it? Did it tell us a lot that because that to me that actually, I thought you were gonna say it goes down because the toll period is shorter. But no, actually, each paycheck. So if a paycheck has an error in California, California is very strict about this. Um, and this is as a GC in my roles, I've always seen it where you literally, um, HR is always like, all right, you got to transition somebody, you better do it on the 15th. So they get their paycheck that day. Because otherwise, you know, you're mailing checks around and it's it's very, very strict and there's these big penalties. Interestingly, so you you get people being like, oh, let's do something nice for the users. Let's pay them every day. But do we want a 7x compliance risk? All right. So that this is a great example. 7x the compliance risk for something marginally more helpful. What do you do? What did you do?

Elana Freeman 20:44

So I said that like this is a risk. And our CPO was like, okay, let me just see what the potential reward is. Because my I consistently message everything is risk reward benefit, like weighing risk and reward, right? If the reward outweighs the risk, we do it, obviously. So I understand risk, you understand reward, you go figure out the reward, the payoff. I can put a dollar value to risk and we can literally just weigh them. So right now, our CPO is going to figure out what the reward is, what the payoff would be, what the impact would be of daily pay. And then we can do as best we can to put a dollar value on risk and measure it, weigh it out, compare it basically. Yeah.

Cecilia Ziniti 21:23

Yeah. I mean, that that's interesting that it's like this is actually one that's pending. So this is like a real, a real, real decision. I'll be curious to see. But I I guess coming in that is like that ability to navigate in in a regulated industry, the ability to be nimble. I mean, that that sets your business apart. So it sounds like I mean, they're they're lucky to have you for sure. All right. So let's talk about how you developed your expertise. And, you know, what I see sometimes with in house leaders and a little bit more with startups, I will admit to this is like I become you become super expert on whatever it is that you. Do. But I talked with a lawyer yesterday, a former AUSA, who now has a big team and has been practicing in-house for 10 years. And she said that she literally, she was like kind of embarrassed. She said to me, She said, I don't remember any of the federal rules of civil procedure except 12v6. And I was like, okay, you know, 10v5 or whatever, I guess that's uh, isn't that the securities law? So whatever, you know, I and we we had a joke the other day in one of our GCA classes that their favorite punctuation mark was the stuff was the section symbol. And I was like, oh, I never, I never have to use that. I don't have it on my keyboard. So how do you keep your skills fresh? And do you sometimes either mourn or have concerns about what this person did, uh, of that you're not like a real lawyer as much anymore?

Elana Freeman 22:50

Yeah, I totally I'm I don't know about concerns, but I miss it. I heard this podcast, I think, last week or week before on on CZ and Friends, and it's like, oh, I miss like the nitty-gritty in the weeds legal analyses. And sometimes I do for sure. But it's okay, so the question is how do I stay brushed up on it?

Cecilia Ziniti 23:08

And to the extent you don't, how do you, you know, either console yourself or make make up for it in other ways? Stay fresh and boring.

Elana Freeman 23:14

So I don't nerd out on legal things necessarily. Like I don't go read court cases. That's never really been fun for me. But what is really cool and interesting and fun is getting really up to speed on on new things that are coming down the pipeline or trying to anticipate and learn. So, and that that excites me. So, AI, for example, you like a few two plus years ago, I was like, AI is coming. I need to get super knowledgeable about this. So I went to conferences, I did CLEs, et cetera. And that's that's exciting and energizing. And it's it's understanding the legal, but it's also understanding the business, right? So that that's more fun to me than the sort of dry legalese. But but I also do, yeah, CLEs. A lot of the law firms offer videos, et cetera. And then, you know, you learn on the job. Like when we first transitioned business models in California to an employment business model, I was not an employment lawyer at that time. Now I consider myself pretty, pretty expert employment lawyer on most things. So I I learned, I learned from outside counsel, et cetera. Yeah.

Cecilia Ziniti 24:17

Do you ever lean to AI? So let's switch topics. Let's talk about AI. So you are a GCAI user, uh pretty deep one. And you, given you we're operating in this regulated industry, what kind of things are you using AI for? And um, has it helped you get up to speed? I mean, employment law, you are absolutely correct. A friend of mine was a DGC at Upwork, and she knows more employment law than I think. I'll she forgets more employment law in a day than I'll ever know. It's amazing. But uh, but yeah, so let's talk about AI. How are how are you using it? How do you think about it? What do you do?

Elana Freeman 24:53

I'll I'll back up a little like on the how am I thinking about it or how I thought about it. So a few years ago, I was seeing AI a lot, and I was like, all right, gotta get the speed, did things, got the speed, and I actually brought it to our leadership team. I was like, here's some proposed policies, let's align on risk tolerance here, roll them out. Okay, fast forward, and I presented them to our product team. This is a great story. And I start off, I'm like, all right, who's using AI? Nothing. I was like, guys, we need to be using AI. Like, I, as your lawyer, am telling you, this is such a powerful tool. So fast forward to now, and like the whole team is using a lot of AI. I we have, of course, our own legal AI tool, GCAI, and it's been how do we use it? Um, okay, so I have saved like 40 plus hours a week, first of all, with AI. I'm definitely a power user. How do we use it? It crosses the gamut. And we use, I use it to summarize documents, I use it to rework my communications, I use it to sanity check my initial gut unemployment law stuff. Yeah. And I think another on the flip side, like it has limitations. Like some of these in the weeds employment law issues, it generally has good like gut check response, but sometimes, right, you you're like, no, that's actually, I can tell that's wrong because whatever. So it's been extremely powerful. And I think it's important to have to not just fully rely on it for an area that you don't know about and that you need to know really specific in the weeds analysis on. Yeah.

Cecilia Ziniti 26:34

So when when you rolled it out, or like how did you get good at it? Saving 40 hours a week is kind of awesome. Did you just like experimentation? Did yeah, you got your your direct report as well. How how did you how did you approach it as a team?

Elana Freeman 26:49

We both took your prompting classes, both of them, which were extremely helpful. We also shared tips, especially close after the prompting classes, like very shortly thereafter. I was like, how are you using it? What's been how what what has been working? How can we experiment? So, like exchanging with Jacob, hey, how do you do this? I tried this today. Now, do you use it this way? How did you use it? Any other creative ways you're using it? So that's like you said, experimentation has been super helpful. Yeah, this GCAI summit you had gave me even more like ideas. Yeah. So I think it can be kind of easy to like learn five ways to use AI and just keep using it in those five ways, but expanding it to like, oh, let me like write this policy, but also please write me a playbook for how to roll this policy out and write me communications to every team directing them on how to roll this policy out, for example, is really, really great. Yeah.

Cecilia Ziniti 27:47

I love it. How about the rest of your company? Like, do you feel like you're able to like with AI, do like like where's legal on AI compared with other other functions at the company? And has it changed how you work either internally or with outside legal?

Elana Freeman 28:05

Yeah. So other teams hit I don't know, they don't have, uh that's not true. I was gonna say they don't have like product specific tools, but they actually do. So our product team has a tool for ENG. That's a that's an Eng specific tool similar to how GCAI is for legal. The rest of the team does generic um clot, I believe. And they, especially over the past six months to a year, have have really used it a lot. Before that, it wasn't that much, which is interesting. So yeah, I was glad I could get ahead of it policy-wise and kind of be the spokesperson for AI whilst also handing over the policy with giving sort of guardrails on how to use it.

Cecilia Ziniti 28:47

Have you um how have you kept your policies a living document? Well, like we we had a great conversation with um TechGC or L Suite on this around, you know, the the like capital P policy for AI, you know, that all of us came up with back in 24 is like kind of stale and doesn't account for agents and it doesn't account for MCP and all these other things. You know, somebody literally made the comment that's like, oh, a policy. That's so quaint. And I was kind of, you know, I thought, okay, you know, like, all right, I uh criticism taken, point noted. Uh so what are you what are you doing? Are you looking at it quarterly? Are you doing it case by case or anything you're doing to keep on the policy side to keep up with the rest of the business as they as they catch up on AI?

Elana Freeman 29:31

Yeah, we have a policy. I'm sure no one has read it. So, and so what we do is I I work it into these legal presentations for each team. Also in a few weeks, in all hands, I'll give a refresher on hey, here's our and I make really simple guidelines on AI, like super high level. Our guidelines are if it is already publicly accessible or you don't care if it is publicly accessible or gets in the hands of a bad actor, go wild. Don't care what you use, don't care what you tool tool it is. If those things are not true, it needs to go through legal. And for our current vetted tools, no personally identifiable or sensitive information goes into them. So it's like pretty, I've tried to make it really simple for the team.

Cecilia Ziniti 30:12

Yeah, it's very simple. I love it. It's also, you know, to me, it maps to the law, right? You know, when you think about this definition of trade secret, you kind of just explained it. I mean, it it's it's really that. And I always think of, you know, it get talking about nerding out. I think of like, okay, you know, the famous case in trade secret that uh the shape of a shipping container. So literally you go to like the port of Oakland and you've got shipping containers, the shape of those. There was a famous case who's like, oh, it's a trade secret. It's like, well, no, it's not. Walk up to the dang container and you can see it, you know, like literally like how it interconnects. And now, of course, you know, all of global commerce goes through these shipping containers that are, of course, interoperable. And it's not a trade secret of whatever company came up with the original thing for that reason. So yeah, I love that. I mean, it's also like, you know, I think we get we I've learned a lot from the security space of like, okay, if you want security policies that people follow, you got to make it easier for them to follow. And, you know, you want people don't inherently want to do the wrong thing. They generally want to do the right thing. It's just that they, they, you know, I think a good policy makes it easy for them to do that.

Elana Freeman 31:18

And I will I'll add one more thing to that is trying to explain the risk is really helpful to incentivize following policy. So I try to do that. It's a little more complicated.

Cecilia Ziniti 31:27

Yeah. So how do you do it? So so we're in your we're in our presentation, we're watching what do I need to do? So, so, so put us in your presentation. What are you saying about risk?

Elana Freeman 31:35

Yeah. So I typically this will be for the team specific presentations. So, like if it's product design design and engineering, the risk is that our intellectual property is no longer ours, right? Um and our product is is key.

Cecilia Ziniti 31:52

That's like I mean, that's okay. It's really the IP. Yeah, yeah, yeah. It's interesting. We had something where I was always um, I used to give the presentations on IP and Read Secret when I was at Amazon. The um interesting example was like, you know, so Apple famously, you know, when you build on the Apple case, if your name was not on the actual um header, you had to say on your LinkedIn or whatever, you had to say that you worked for a Cupertino-based electronics company. And it's like, okay, well, you maybe maybe you can figure that out. But no, the uh the example that I used in those cases was that we had an intern in one of the groups that the intern's assignment for the summer was to figure out if a particular algorithm could be used to optimize something in the product. And it was not an easy answer. It was literally like whatever, 10 weeks of work for this person to figure out. It turned out, sadly, the answer was no, you could not use that algorithm for whatever it was. You know, but that's still a trade secret because it's gonna take company Y, that's not your company, 10 weeks to figure it out themselves. And so even though it wasn't even part of the product, you know, that was the example that we used. And so it's nice to make it to make it grounded. And also in your case, I'm hearing that you're making the training specific to the group of like what they care about. It's literally their livelihood, right? So making it real in that way. Um, I love that too. All right. Uh, you said before that people should take what works for them in careers and leave the rest. It's, you know, I've also heard like the version of this advice that's given to founders is like, know which investors' advice to ignore. So I heard that too. How does that show up? And when when did you get to that point in your career where you could know that you yourself had the judgment to be able to ignore some advice, or some advice would be bad?

Elana Freeman 33:46

So this came in my first year of law school. This is a random funny story. I asked like a 2L or 3L. I was reading his case and I was like, how do you know like who's the appellant? Um, and this like 2L or 3L, whatever they were, I was like, oh yeah, appellant is always a plaintiff. And I was like, oh, okay, okay. And then very quickly I realized that is just not objectively false. Like, right? What? And I think, I mean, throughout law school, I was always, and even in my early years of my career, I was really like, I was doing a lot of informational interviews and trying to get input and advice from people who were doing what I wanted to do or who had, you know, established careers. And everyone wants to give their advice and opinion as if it's like the truth, right? Because it is a truth for them. But then in I want to say three, four past three or four years, um, it's become so clear to me that that's their advice, right? For their career and their specific set of circumstances. And that really might not be the case for everyone, but it's not, it's not necessarily applicable to everyone. So I think, and this even goes beyond law, right? There's this whole like personal development world out there, and everyone talks as if their opinion is like, this is the thing that will save everything and make everything better. And that's just that's what worked for them. And it shouldn't be taken as like capital T truth ever. Um I love that.

Cecilia Ziniti 35:15

It was it was a journey for me to realize that too. And you know, there's a flavor too that's like they're trying to sell a book or trying to whatever, and everybody has their own point of view. And so it got to the point where one of my favorite investors said, or, you know, there was a podcast with the CPO of Rippling on Lenning's podcast, super popular. And he basically said, There is no advice. There's just here's what I've experienced and extrapolate that from what you will. Because of course, things are different. Like we deal with this now where, you know, GCAI, our growth and the kind of startup journey is really, really high, you know, but that's in a new era of AI. So if you compare us with other AI companies, it's still high, but it's not crazy high. And it's like, okay, we can we need to be benchmarking against the best and doing this kind of situation-specific advice. That balance story, though, that one takes a cake. It's always a tiny. So good. Today it is February now, and it's a perfect February where uh let's see, what is it? So the the dates on the calendar all match up to calendar dates. And there was a tweet that was like, this hasn't happened in 854 years. And I read that and I was like, oh wow, that's so interesting. And then my husband's like, no, actually, it's like every whatever, seven years, 7.5 because of the leap year, but like this is not like, you know, like you're so dumb. Anyways, uh, I I I agree with that, but uh kudos to you for for having the gumption and and realizing it, uh, the the wider point. If somebody listened to this episode and want to understand how you operate, what would you what would you tell them?

Elana Freeman 36:43

Um people first. I really spend a lot of time vetting, interviewing, training, making people feel like I care and I want to mentor them and train them and that we're a team. And also, yeah, the trust within the rest of the company is really important. Um the other thing is I'm really kind of obsessed with with results, like business-centric results and how can we continue to add value and be a thought partner to get those results. And just keep getting better and better. I think that's the name of the game is like how can I keep growing as a leader, as a person, but that that creates fulfillment and good teams.

Cecilia Ziniti 37:29

I love that. I mean, the curiosity point and then the one of our GCI principles is one percent better every day. And of course, you know, that the book talked about an atomic habit book talk talks about is compounding, right? So it's like 38 times better in a year. So I love that. Um, all right. So on the topic of books in the lightning round, what's a book, idea, or mentor that has shaped how you lead?

Elana Freeman 37:52

I have two mentors. I don't know that so and I have more than this, right? But for listeners, they're very accessible. Tar Brock, T-A-R-A, Brock is how you B-R-A C is how you spell it. She's mindfulness, meditation teacher. She's fantastic. I think being an awesome leader starts with yourself, right? And your own personal universe. So Tony Robbins has been like his, he has his rapid planning method, is fantastic. He he has some really good, as like kind of cheesy as like some of his uh, you know, one-liners might sound, he has some really great tactical tools.

Cecilia Ziniti 38:29

What's a myth about being a general counsel or uh or running compliance that you would debunk or that that you think people believe that is not true?

Elana Freeman 38:40

I don't know if people think this, but I think often people think you have to know everything about everything. Like I am a true generalist, but I don't know everything about everything. Like you need to know when to outsource to outside counsel, right? You need to know what you know and where the limit is and what's important enough to outsource.

Cecilia Ziniti 38:59

And um of everything you've achieved, you've very accomplished. I'm gonna I'm gonna take a question from how I built this, because somebody said we're how I built this for legal. How much of it has been luck versus hard work?

Elana Freeman 39:11

Some of it's certainly luck. I'm trying percentage-wise. If we say how much of it is hard work, it's a lot, but it's not just my hard work, right? I work hard, but there's so many other, I mean, I was just thinking the other day of like all the people whose whose shoulders I stand on, who built the world we live in today, where like I, as a woman, et cetera, et cetera, can like do what I'm doing. So it's, I don't know, I'm gonna give it 60% hard work, not just me, but a gajillion other people who like created the universe that allows me to do this. Uh and 40%, yeah, pure luck for sure.

Cecilia Ziniti 39:44

I love it. I love it. Any closing thoughts you want to leave listeners with?

Elana Freeman 39:50

You create your own reality. You can create your own the legal function that you want. You can create the own career you want. Sky's the limit. Think about it, write it down, make it happen. You can do it.

Cecilia Ziniti 40:03

Love that. Thank you so much for joining and sharing your perspective, Elana. Thank you. That was my conversation with Elana Freeman, the head of legal and compliance at Swing Education, and a leader that brings clarity and joy to how legal operates today. Follow CZ and Friends wherever you get your podcasts. To learn how legal teams are using AI to work smarter, lead with impact, and reach the sky's the limit, visit gc.ai. Thank you for listening. We'll see you next time.