Scaling Legal in Education’s Complex Regulatory Landscape: Elana Freeman of Swing Education

[0:00] Illinois has a spun Chicago teachers

[0:02] pension fund requirement for certain

[0:04] teachers where you have to contribute to

[0:06] this fund and we were like all right

[0:08] fine we'll contribute to this fund but

[0:11] CTPF as they call it wasn't answering

[0:13] our calls etc so I just showed up at the

[0:15] building and I was like hey can I talk

[0:17] to your I don't remember who the title

[0:18] was and they were like yeah sure I just

[0:20] got a meeting when they were just

[0:21] completely not answering our questions

[0:23] it was great

[0:29] welcome back to CZ and Friends where we

[0:31] talk with legal leaders, operators, and

[0:32] technologists shaping how modern

[0:34] companies work. I'm your host, Chichilia

[0:37] Zeniti. Today, I'm joined by Elana

[0:39] Freeman, the head of legal and

[0:40] compliance at edtech company Swing

[0:42] Education. She's built and scaled legal

[0:44] at a fast growing edtech company

[0:46] operating in one of the messiest

[0:47] regulatoratory environments you can

[0:49] imagine. And I know because I was a GC

[0:51] of an education company. It's regulated

[0:53] by state. You're dealing with children.

[0:55] You're dealing with all kinds of issues

[0:57] across federal, state, local, and even

[1:00] municipal law. And she's done it with a

[1:03] people first approach, obsessed with

[1:05] clarity and speed. What I love about

[1:07] Alana is that she doesn't make legal the

[1:09] loudest voice in the room. She builds

[1:10] trust, creates the conditions for good

[1:12] decision-m, and helps teams move faster.

[1:14] All the good stuff we love about

[1:16] in-house counsel. So, let's dive in.

[1:19] Elana, welcome to the show. Good to be

[1:21] here. So, you've said something I like

[1:23] in your in your public post. You said

[1:25] great leadership is not about control,

[1:28] but it's more like how to create

[1:30] conditions so good decisions happen

[1:33] consistently and quickly. Unpack that a

[1:36] little bit.

[1:37] Yeah, it's it's a lot of facets. I think

[1:40] one is building a great team. If I can

[1:43] be hands-on on every single decision, so

[1:46] my team needs to make good decisions and

[1:48] be equipped to do so quickly um and

[1:50] effectively. And the other piece is

[1:51] trust. Trust with your executive team,

[1:53] trust with the entire company. So I can

[1:57] say more about strategically how we do

[1:59] that. But that's a high level.

[2:00] Got it. So you joined swing as a

[2:03] compliance manager and got promoted

[2:05] through to now you run legal. Did you

[2:07] use those techniques to to do that or

[2:09] like like was this did you come to this

[2:11] through experimentation? Like what what

[2:13] does it mean? And then yeah, I'd

[2:14] absolutely love to dig a little further

[2:17] of like okay trust. Everybody talks

[2:18] about trust. give us an example and make

[2:20] it real for us.

[2:21] Yeah. So I came yes I came in as

[2:23] compliance manager. It was a mixture of

[2:25] of legal compliance and business

[2:26] development. It was a small company at

[2:28] the time. I think I built trust because

[2:30] right we were we were in person. It was

[2:32] a 40 person company. We all knew each

[2:34] other and I wasn't the legal person when

[2:36] I joined. So that trust was built

[2:38] organically. It wasn't intentional. And

[2:40] then over time as my role grew, as a

[2:42] company grew, as we became remote fully,

[2:44] as we converted to an employment

[2:46] business model in California, and my

[2:48] role became legal, head of legal, etc.,

[2:50] I realized that that trust that was so

[2:53] organic and easily built in the

[2:55] beginning wasn't necessarily coming

[2:58] through, right? If someone's hired

[2:59] remotely and then 10 and 20 people are

[3:02] hired remotely who don't know me, then

[3:04] you know if someone's ahead of legal,

[3:07] you're you hear no matter what you say,

[3:10] no matter what the legal person says. So

[3:11] I realized, okay, this is not to be

[3:13] taken for granted. How do I build trust?

[3:16] And part of it was, and we can dive into

[3:17] this later, these legal team

[3:19] presentations with every single team

[3:21] across the company. I was like, we need

[3:23] to help them know who we are, chat with

[3:26] us, build trust that way. um and bring

[3:28] them in on legal so they actually

[3:31] understand the risks we're dealing with

[3:33] that their team is dealing with and can

[3:34] issue spot on their own and they don't

[3:36] feel like legal is just telling them no

[3:39] all the time. Part of those

[3:40] presentations also were to help it be

[3:44] very clear that we are a team. We are

[3:46] not telling you yes or no. We are

[3:49] working together. We know the risk. You

[3:50] know the business outcome. You know the

[3:52] what your team does best. So, we need to

[3:54] work together to make sure we're

[3:56] mitigating appropriate risk and some

[3:58] risk is really okay to be, you know, to

[4:01] let to let go. Um, we're a startup,

[4:03] right? We have a healthy risk tolerance.

[4:06] Those are a few ways, you know, we have

[4:07] office hours. We talk to people in

[4:09] layman's terms. We really try to not be

[4:12] a team that talks in legal and is just

[4:16] saying yes no. So, Swing Education's

[4:19] business model, looking at your

[4:21] LinkedIn, you actually started in 2019.

[4:23] And Swing Education, it looks like it's

[4:25] software around connecting schools with

[4:28] substitute teachers. So, this this this

[4:30] feels like a like like a law school

[4:32] hypo, but what's the like orienting us a

[4:34] little bit? What what is the what are

[4:36] the core legal questions that that you

[4:38] deal with? And is the business model is

[4:40] is it like Uber where you're you got the

[4:43] contractors

[4:44] or orient us as though we're we're new

[4:47] product council starting on your team.

[4:48] You're going to give us you're going to

[4:50] give us an overview what's what's going

[4:51] on at your company and then come with

[4:54] some real examples around that around

[4:55] around how you how do you educate the

[4:57] business on that too.

[4:58] Yeah. So I h highest risk legal stuff um

[5:02] is probably employment and mis

[5:05] employment laws in California and

[5:06] mclassification in other states.

[5:09] The complicated piece about this is

[5:11] we're in seven states across the US. We

[5:13] have decided to operate two different

[5:15] business models. Some states we operate

[5:17] an independent contractor purely were a

[5:19] platform gig economy platform.

[5:22] So I am you know Sunnydale Elementary

[5:25] School and I need a substitute teacher.

[5:27] I go to swing and it's it's like looking

[5:29] on LinkedIn or like what what is the

[5:31] actual how does the product work? But

[5:33] how does Okay, so the product is

[5:35] basically as a sub you set up, meaning

[5:38] you tell us here's my credential, here's

[5:40] my background check, I'm okay to teach

[5:41] from a legal perspective. Once you give

[5:43] us that information, you're able to view

[5:45] requests that our school partners post

[5:47] on the platform. In California, you're

[5:49] an employee. We operate an employment

[5:50] business model in California.

[5:52] That's where the tricky compliance stuff

[5:54] comes in. And then as a school, you're

[5:55] like, I need a sub. Let me just quickly

[5:57] post it on the swing platform. And then

[5:59] it's automatically viewable by like, you

[6:01] know, hundreds of subs in your region to

[6:03] accept it and show up at your school.

[6:05] Got it. Okay. Yeah.

[6:06] Yeah. I mean, I've used every, you know,

[6:08] I have kids and I've used every kind of

[6:10] child care matching service in the

[6:12] books, right? So, it's always

[6:13] interesting because you, you know, this

[6:15] two-sided marketplace, you got to worry

[6:16] about compliance on both sides, right?

[6:19] So, um, interesting. Okay. And then do

[6:22] you actually vet the teachers then for

[6:24] qualifications? So you have to deal with

[6:26] certification compliance and and all

[6:28] that as well.

[6:29] Yep.

[6:30] Got it. Okay. All right. So when you

[6:33] joined in 2019, give us a from two

[6:35] journey. So you joined in 2019 and co

[6:39] hadn't happened yet and you were a

[6:41] compliance manager and so you were

[6:43] basically it was mostly employment law

[6:45] at that time. So then what did you build

[6:47] and how did how did the company grow?

[6:49] Yeah, it was actually it wasn't

[6:50] necessarily employment, it was

[6:52] compliance. It was substitute teacher

[6:53] compliance requirement. So exactly the

[6:55] certifications, background checks, etc.

[6:57] They're different in every state. Some

[6:59] schools have their own separate

[7:00] requirements. It's actually really can

[7:03] get really complicated and it changes.

[7:05] So that was a primary role. It was that

[7:09] and we were looking to develop a new

[7:10] market. So I opened up Illinois as a

[7:12] market.

[7:14] So it was let's make sure we're vetting

[7:17] new markets appropriately as in taking

[7:19] into account the compliance piece which

[7:20] was not a concerted effort a concerted

[7:23] role before.

[7:23] So this is like bringing back my edtech

[7:26] GC days. We had my team had a map that

[7:28] was like how many states are we good in

[7:30] and literally was like I'm very visual

[7:32] right I majored in international

[7:34] relations so I had at one point knew

[7:36] that knew the world map but basically we

[7:37] had a map where it was like basically

[7:39] red yellow green of like and some states

[7:41] you know it is I mean education of

[7:43] course under the constitution right is a

[7:46] matter for the states and so you get

[7:48] lots of different lots of different

[7:49] requirements okay so you come in and

[7:51] you're you're doing the compliance in

[7:52] the in the one state and then you're

[7:54] like all right we're going to open up

[7:55] Illinois so that's a huge scale legal

[7:57] project. How did you how did you do it?

[8:00] Any fun stories along the way?

[8:03] I have such a fun story actually. So,

[8:04] okay, we were in at the time six states

[8:06] and we were opening the seventh in

[8:08] Illinois. So, Illinois has a spun

[8:10] Chicago teachers pension fund

[8:12] requirement for certain teachers where

[8:14] you have to contribute to this fund. And

[8:16] we were like, all right, fine. We'll

[8:18] contribute to this fund. But CTPF, as

[8:20] they call it, wasn't answering our

[8:22] calls, etc. So, I just showed up at the

[8:23] building and I was like, hey, can I talk

[8:26] to you? I don't remember what the title

[8:27] was and they were like, "Yeah, sure."

[8:28] So, I just got a meeting when they were

[8:30] just completely not answering our

[8:31] questions. It was great. It turns out we

[8:33] didn't have have to contribute to the

[8:35] fund. We can't logistically. But that

[8:37] was a great story just showing up in

[8:38] person. I think having

[8:40] it's showing up in person. I think

[8:42] particularly it's like,

[8:43] you know, and we've we've talked about

[8:45] this theme on the podcast too of like

[8:46] regulators are humans too. you know,

[8:49] anybody that works at a court, any clerk

[8:50] of court, a judge, there's, you know,

[8:53] this interesting research that, you

[8:54] know, judges give worse sentences on

[8:56] Monday mornings than any other time. You

[8:58] know, this kind of like that that people

[9:00] are human. So, you show, so you go you

[9:02] go to the regulator and you and it

[9:04] sounds like you got what you needed.

[9:06] Yeah, it was like a it was like

[9:07] impromptu hourlong meeting without any

[9:10] re-scheduling or anything. It was great.

[9:13] So, okay. So then so you launched

[9:15] Illinois and how do you systematize that

[9:18] kind of compliance because I think

[9:19] that's something especially in an AI

[9:20] world that a lot of folks are thinking

[9:23] about. So, so tell us like and then you

[9:25] know you mentioned building trust. You

[9:27] said early it was easy, but then you

[9:29] know you do things like open up

[9:31] Illinois, brand new line of business,

[9:33] you know, at least 17th of your of your

[9:35] company's revenue. I have to think you

[9:37] earn trust that way, right? So talk

[9:39] about both things. Talk about like what

[9:40] is the machine that you had to build and

[9:42] then and then how did um what was the

[9:45] business reception of that? Yeah. So I

[9:48] mean we were lucky that we had already

[9:50] had the infrastructure for the

[9:52] compliance piece because our product

[9:54] team has built on the back end sort of

[9:56] modules to take subs through like here's

[9:59] where you put your certificate

[10:01] here's your background check module etc.

[10:03] So I just had to really map it out and

[10:06] hand it to our product team to

[10:07] productize it. So that piece we already

[10:10] had a skeletal infrastructure um in

[10:13] place from California etc because

[10:14] they're similar they're not the same

[10:16] requirements but they're similar enough

[10:18] um and we also we have a sub operations

[10:21] team right who's looking into background

[10:23] checks and updating background checks so

[10:25] that part was actually pretty easy I'm

[10:27] lucky in that in that sense that we're

[10:29] very product centric on building trust I

[10:32] think you know it was organic and easy

[10:34] at the time and everyone at the time and

[10:36] still knows that schools value

[10:38] compliance right your reputation and

[10:42] client base is not going to grow if you

[10:44] don't meet those compliance requirements

[10:45] so from that respect is very aligned and

[10:48] easy then you know nowadays

[10:51] like AI policies for example is like

[10:54] it's a different there's a friction

[10:56] there between like our team wants to

[10:58] just use AI but for everything right and

[11:00] I'm like okay but there's some

[11:02] limitations here how do we and that's

[11:04] maybe a little trickier um Interesting.

[11:08] Well, so so you honed on something

[11:10] interesting which is so your schools are

[11:12] your customers. Um and there is a whole

[11:14] class of companies

[11:17] um like Vanta would be one of them where

[11:21] you know any any legal tech but also you

[11:24] know Carta which does equity management

[11:27] Vanta which does compliance for sock 2

[11:30] for technology companies where the

[11:32] product is really compliance and in that

[11:35] scenario legal has this like extra

[11:37] special role it sounds like it's sort of

[11:39] similar with you too right so a school

[11:40] is getting when they when they hire you

[11:42] or when they they go through your

[11:44] marketplace, they're getting the

[11:45] substitute, but they're getting the

[11:47] substitute that they know has been

[11:48] background checked, that they know has

[11:50] met the minimum, you know, master's

[11:51] degree or whatever it is they need. How

[11:54] does the fact that your company sells

[11:56] compliance kind of it sounds like you

[11:59] think it makes your job easier? Any

[12:00] other impact that it has for you as a as

[12:03] a leader of of a legal team?

[12:06] I think yeah, it makes my job a lot

[12:07] easier for that facet of legal and

[12:10] compliance for sure. Um, I think I think

[12:12] you nailed it. It does for that. I mean,

[12:14] there's other facets, right, of legal

[12:15] compliance that is not as

[12:17] straightforward, but that piece is

[12:19] pretty aligned. And there's of course

[12:20] friction where

[12:22] ideally the minimum requirements

[12:25] possible increase the number of subs we

[12:27] have who are subsidy teachers who are

[12:29] vetted and ready to go. We also

[12:32] understand that that's not what our

[12:33] schools want. I'd say it's yeah, it

[12:36] makes my job relatively easy in that.

[12:38] Amazing.

[12:40] Let's talk about co real quick. So it's

[12:42] been five years, but

[12:46] you know, is it fair to say your company

[12:48] came out stronger? What was the what was

[12:50] the process? I mean, did business stop

[12:52] completely for a while, but I have to

[12:54] imagine actually substitutes you

[12:55] probably need more in co so what was the

[12:58] what was the business impact and then um

[13:01] let's talk about that first. What was

[13:02] it? How did how did that affect you as a

[13:05] leader company and then you as a leader?

[13:07] Yeah, co our I mean our our business

[13:10] went to complete zero overnight because

[13:12] schools closed so no one needed subsidy

[13:14] teachers and we had zero revenue. So

[13:16] that was rough and as schools you know

[13:18] we that was interesting because we

[13:20] started we spun off pods for a little

[13:23] while right when schools were closed

[13:25] families were wanting teachers for their

[13:28] pod if you remember this term during

[13:30] COVID. So that was kind of

[13:33] you had families as customers then.

[13:35] Correct. So we would try to like white

[13:37] glove match really good substitute

[13:39] teachers with families. We looked into

[13:42] we looked into a bunch of stuff. We

[13:43] looked into tutoring, right? Remote

[13:45] tutoring options. None of those really

[13:48] panned out. So I think once schools came

[13:51] back on, it was like we need subs now

[13:54] and we realized we needed to recruit

[13:56] quickly and we had we didn't have the

[13:58] supply needed. So that was a bit tricky.

[14:01] Um, but then after, you know, after that

[14:03] all balanced out, it was business as

[14:06] usual. I mean, schools had this co

[14:08] funding which helped them get more subs,

[14:11] but it was a bit of a roller coaster

[14:13] until it all evened out for sure.

[14:16] Wow. So, getting through that and

[14:19] presumably now, so it sounds like your

[14:20] business is healthy now, 6 years later.

[14:23] Um,

[14:25] any enduring lessons from that or

[14:28] relationships? You mentioned trust. Any

[14:31] anything that you can that that's coming

[14:33] to mind?

[14:34] I think the ability to be nimble is

[14:36] really important in those types of

[14:38] scenarios. Like the pods thing didn't

[14:40] work out. However, we were able to get

[14:42] some revenue when we otherwise wouldn't

[14:44] and we were able to just spin up this

[14:46] new product like you know overnight

[14:48] basically. Um and that was a good

[14:51] learning for me. Um I think yeah I was

[14:55] like we need to build terms of service.

[14:56] We need to build everything surrounding

[14:58] this new business. So I think the

[15:00] lessons there are how important it is to

[15:02] be nimble because things happen right

[15:04] and

[15:06] yeah and the trust piece helped with

[15:08] that. We had a team that was like

[15:09] decently small who knew each other

[15:11] decently well. So we really all

[15:15] galvanized came together really easily

[15:17] to make that happen.

[15:19] You mentioned nimleness. You've also

[15:21] talked in the past about building a

[15:22] lean, high performing Leela team. What

[15:24] does efficiency mean? And are there

[15:27] specific indicators where you're like,

[15:28] "All right, we're getting bloated.

[15:30] We're, you know, we're moving too slow.

[15:32] We're not being nimble enough." And what

[15:34] how do you quash those instances?

[15:37] Yeah. Yeah. I'm kind of obsessed with an

[15:38] efficient legal team.

[15:41] Um, so I think what efficiency means,

[15:44] it's not necessarily working quickly. I

[15:47] think from a and this is of course from

[15:49] a startup perspective, understanding

[15:52] what are our highest risks that we

[15:55] really do need to dot our eyes and cross

[15:57] our tees on and what are the ones that

[16:00] are medium that we want to kind of

[16:01] mitigate and what are the ones that are

[16:03] just not super risky and aren't worth

[16:05] the effort and getting really being

[16:07] thoughtful and getting really clear on

[16:09] that. And that includes discussing and

[16:12] getting aligned in some instances with

[16:14] leadership, right? Like I mentioned, our

[16:15] AI policy, other ones are kind of just

[16:17] purely legal, but

[16:20] but yeah, and then making sure your team

[16:23] understands what those pri priorities

[16:26] are. What are things that are really

[16:27] higher risk, what are medium, what are

[16:29] low, so that they can execute against

[16:31] that and prioritize really effectively.

[16:34] But when people when you come in as a as

[16:37] a boss and you're feeling that someone's

[16:40] not prioritizing, like let's get super

[16:42] brass taxed. Do you literally like have

[16:44] a list or like you know we had a

[16:46] situation at our company where basically

[16:48] somebody spent like two days rearranging

[16:52] folders and it was like what is going on

[16:54] and you know and you kind of like see

[16:56] that you're like well I mean it's good

[16:58] that they're well arranged and and

[17:00] probably a nice end result

[17:03] you know you almost wonder as a manager

[17:06] like you know if the person deres joy

[17:08] from rearranging folders like you know

[17:10] that's cool but then you're like well

[17:12] you know is that really the right

[17:13] priority? And and then, you know,

[17:15] there's there's been some uh leadership

[17:19] uh writing from Ben Horowitz where he

[17:22] literally he has a book called The Hard

[17:24] Thing About Hard Things and he talks

[17:26] about being a CEO and he says that he

[17:28] would kick off meetings or if he saw

[17:30] this happening, he would literally say

[17:32] that is not the effing priority. And to

[17:34] him, it was important to actually use

[17:36] the f- word to underscore like it just

[17:38] isn't. And yeah, that's obviously an

[17:40] extreme version, but if you said, okay,

[17:42] you're obsessed with efficiency. You

[17:44] help the team with priorities. What do

[17:46] you do when you see it going wrong and

[17:49] have you done it? Maybe give us some

[17:51] examples. Yeah. Okay. I I have two

[17:53] advantages here. One, we're a team of

[17:55] two. I have one direct report. So, we

[17:58] have the advantage of a really close

[17:59] working relationship.

[18:00] The way I do it with him, well, one, you

[18:02] know, we're lean. We don't have a lot of

[18:04] time. He needs to prioritize.

[18:06] Yep.

[18:07] Two is if he comes to me and he is like,

[18:10] "Here's this issue. I'm going to like

[18:12] appeal it or do this thing or whatever."

[18:15] I consistently ask him when he brings

[18:17] projects to me, "Is this some version of

[18:20] is this worth our time? What is the

[18:22] outcome we're getting from this

[18:24] project?" And I do that across the

[18:26] board. Like when we talk about things,

[18:28] my main question is what is the goal and

[18:31] what is our outcome and what is the

[18:32] impact? So me just asking those

[18:35] questions consistently throughout our

[18:37] working relationship means he is now

[18:39] asking the same questions and coming to

[18:41] me with the answers proactively right so

[18:44] he has already done this analysis in his

[18:47] head of what is the the impact of this

[18:51] is it worth it have you tried this with

[18:53] your leadership team

[18:56] um in the sense that you know as a

[18:58] general counsel as a head of legal you

[19:00] know you have maybe not as many direct

[19:02] reports But arguably you're responsible

[19:05] for, you know, or you in name at least

[19:06] are responsible for compliance of, you

[19:08] know, the hundreds of employees and

[19:10] then, you know, potentially thousands of

[19:11] of of contractors and and you know, the

[19:15] people that provide the swing service.

[19:17] So, how do you you know, when you've got

[19:19] when you think something is going wrong

[19:21] or you're in an executive meeting and

[19:23] you're like, "Oh god, I don't think

[19:25] that's a good idea." Put us in your

[19:26] shoes and what do you do? I try to

[19:29] really bring translate the law into

[19:31] layman's terms and be presented as a

[19:34] thought partnership like hey there's a

[19:37] legal flag there. I don't know if I

[19:39] would necessarily say it that way,

[19:40] right? But this is the risk posed,

[19:43] right? For example, and I'll give you a

[19:45] concrete example. In California, if we

[19:47] switch from weekly pay for employees,

[19:50] these are hourly non-exempt.

[19:53] If we switch from weekly pay to daily

[19:55] pay, our potential liability goes up by

[19:58] 7x.

[20:00] Wow.

[20:02] Is this under PA or what's it? tell us a

[20:04] lot about that because that to me that

[20:05] actually I thought you were going to say

[20:06] it goes down because whole period is

[20:10] shorter but no actually each paycheck so

[20:12] if a paycheck has an error in California

[20:14] and California is very strict about this

[20:17] um and this is as a GC in my roles I've

[20:19] always seen it where you literally um HR

[20:22] is always like all right you got to

[20:23] transition somebody you better do it on

[20:24] the 15th so they get their paycheck that

[20:26] day because otherwise you know you're

[20:28] mailing checks around and it's it's very

[20:29] very strict and there's these big

[20:31] penalties interestingly so you you get

[20:33] people being like, "Oh, let's do

[20:34] something nice for the users. Let's pay

[20:35] them every day." But do we want to 7x

[20:38] compliance risk? All right. So, that is

[20:40] a great example. 7x the compliance risk

[20:42] for something marginally more helpful.

[20:43] What do you do? What did you do? So, I

[20:45] said that like this is a risk and our

[20:47] our CPO was like, "Okay, let me just see

[20:50] what the potential reward is cuz my I

[20:53] consistently message everything is

[20:55] riskreward benefit like weighing risk

[20:57] and reward, right? If the reward

[20:59] outweighs the risk, we do it obviously."

[21:01] So I understand risk, you understand

[21:03] reward. You go figure out the reward,

[21:05] the payoff. I can put a dollar value to

[21:07] risk and we can literally just weigh

[21:08] them. So right now our CPO is going to

[21:12] figure out what the reward is, what the

[21:13] payoff would be, what the impact would

[21:14] be of daily pay, and then we can do as

[21:17] best we can to put a dollar value on

[21:19] risk and and measure it, weigh it out,

[21:22] compare it basically. Yeah.

[21:24] Yeah. I mean that that's interesting

[21:25] that it's like this is actually one

[21:26] that's penny. So this is like a real a

[21:28] real a real real decision. I'll be I'll

[21:29] be curious to see. But I I guess coming

[21:31] in that is like that ability to navigate

[21:35] in in a regulated industry, the ability

[21:37] to to be nimble. I mean that that sets

[21:39] your business apart. So it sounds like I

[21:42] mean they're they're lucky to have you

[21:43] for sure. All right. So let's talk about

[21:47] how you developed your expertise. And

[21:50] you know what I see sometimes with

[21:51] in-house leaders and a little bit more

[21:54] with startups, I will admit to this is

[21:56] like I become you become super expert on

[21:59] whatever it is that you do. But I talked

[22:01] with a lawyer yesterday, a former a USA

[22:04] who now has a big team and has been

[22:06] practicing in house for 10 years. And

[22:10] she said that she literally she was like

[22:12] kind of embarrassed. She said to me, she

[22:14] said, "I don't remember any of the

[22:15] federal rules of civil procedure except

[22:17] 12v6." And I was like, okay, you know,

[22:21] 10v5 or whatever. I guess that's isn't

[22:23] that the securities laws or whatever.

[22:25] You know, I I I and we we had a joke the

[22:27] other day in one GCA classes that their

[22:29] favorite punctuation mark was this was

[22:31] the section symbol. And I was like, I

[22:34] never I never have to use that. I don't

[22:35] have it on my keyboard. So, how do you

[22:38] keep your skills fresh? And do you

[22:40] sometimes

[22:41] either mourn or have concerns about what

[22:44] this person did of that you're not like

[22:47] a real lawyer as much anymore?

[22:50] Yeah, I totally I don't know about

[22:52] concerns, but I miss it. I heard this

[22:54] podcast I think last week or week before

[22:55] on on CZ and friends and like oh I miss

[22:58] like the the nitty-gritty in the weeds

[23:00] legal analyses and sometimes I do for

[23:03] sure but it's okay. Okay. So the

[23:05] question is how do I stay brushed up on

[23:07] stay fresh and to the extent you don't

[23:09] how do you you know either console

[23:11] yourself or make up for it in other ways

[23:13] stay fresh and boring.

[23:14] So I don't nerd out on legal things

[23:17] necessarily like I don't go read court

[23:19] cases. That's never really been fun for

[23:21] me. But what is really cool and

[23:22] interesting and fun is getting really up

[23:24] to speed on on new things that are

[23:26] coming down the pipeline or trying to

[23:28] anticipate and learn. So and that that

[23:31] excites me. So AI for example like a few

[23:34] two plus years ago I was like AI is

[23:36] coming I need to get super knowledgeable

[23:39] about this. So I went to conferences I

[23:41] did CLE etc and and that's that's

[23:44] exciting and energizing and it's it's

[23:45] understanding the legal but it's also

[23:47] understanding the business right so that

[23:49] that's more fun to me than the sort of

[23:52] dry legalies but but I also do yeah cl a

[23:55] lot of the law firms offer videos etc.

[23:58] And then you know you went on the job

[24:00] like when we first transitioned business

[24:02] models in California to an employment

[24:04] business model. I I was not an

[24:07] employment lawyer at that time. Now I

[24:08] consider myself pretty pretty expert

[24:11] employment lawyer on most things. So I I

[24:13] learned I learned from outside counsel

[24:15] etc. Yeah. Do you ever lean to AI? So

[24:19] let's switch topics. Let's talk about

[24:20] AI. So you are a GCI user uh pretty deep

[24:24] one and you given you operating this

[24:27] regulated industry.

[24:29] What kind of things are you using AI

[24:31] for? And um has it helped you get up to

[24:35] speed? I mean employment law, you are

[24:38] absolutely correct. Friend of mine was a

[24:41] DGC at Upwork and she knows more

[24:43] employment law than I think I'll she

[24:45] forgets more employment law in a day

[24:46] than I'll ever know. It's amazing. But

[24:48] uh but yeah, so let's talk about AI. How

[24:50] how are you using it? How do you think

[24:52] about it? What do you do?

[24:53] I I'll back up a little like on the how

[24:55] am I thinking about it or how I thought

[24:56] about it. So a few years ago I was

[24:58] seeing AI a lot and I was like all right

[24:59] got to get up to speed. Did things got

[25:01] up to speed and I actually brought it to

[25:03] our leadership team. I was like here are

[25:06] some proposed policies. Let's align on

[25:08] risk tolerance here and roll them out.

[25:11] Okay. Fast forward and I presented them

[25:13] to our product team. This is a great

[25:15] story. And I start off I'm like all

[25:17] right who's using AI? Nothing.

[25:20] I was like, "Guys, we need to be using

[25:23] AI." Like I, as your lawyer, I'm telling

[25:25] you, this is such a powerful tool. So,

[25:29] fast forward to now and like the whole

[25:31] team is using a lot of AI. I we have of

[25:33] course our own legal AI tool, GCI, and

[25:36] it's been how do we use it? Um, okay.

[25:39] So, I have saved like 40 plus hours a

[25:41] week, first of all, with AI. I'm

[25:43] definitely a power user.

[25:46] How do we use it? It crosses the gamut

[25:50] and we use I use it to summarize

[25:52] documents. I use it to rework my

[25:55] communications. I use it to sanity check

[25:57] my initial gut on employment law stuff.

[26:00] Yeah. And I think another on the flip

[26:02] side like it has limitations like some

[26:04] of these in the weeds employment law

[26:06] issues.

[26:08] It generally has good like gut check

[26:11] response but sometimes right you you're

[26:14] like no that's actually I can tell

[26:16] that's wrong because whatever. So it's

[26:19] been extremely powerful and I think it's

[26:21] important to have to not just fully rely

[26:24] on it for an area that you don't know

[26:26] about and that you need to know really

[26:29] specific in the weeds analysis on. Yeah.

[26:35] So when when you rolled it out or like

[26:37] like how did you get good at it? Saving

[26:39] 40 hours a week is kind of awesome. Did

[26:41] you just like experimentation?

[26:44] Did you got your your direct report as

[26:46] well? How did you how did you approach

[26:48] it as a team?

[26:50] We both took your prompting classes both

[26:52] of them

[26:53] which were extremely helpful. We also

[26:55] shared tips especially close after the

[26:58] prompting classes like very shortly

[27:00] thereafter. I was like how are you using

[27:01] it? What's been what what has been

[27:03] working? How can we experiment? So like

[27:05] exchanging with Jacob, hey, how do you

[27:08] do this? I tried this today. Do you use

[27:11] it this way? How did you use it? Any

[27:12] other creative ways you're using it? So

[27:14] that's like you said, experimentation

[27:16] has been super helpful. Yeah, this GCAI

[27:19] summit you had gave me even more like

[27:22] ideas. Yeah. So I think it can be kind

[27:25] of easy to like learn five ways to use

[27:28] AI and just keep using it in those five

[27:30] ways. But expanding it to like oh let me

[27:32] like write this policy but also please

[27:35] write me a playbook for how to roll this

[27:37] policy out and write me communications

[27:39] to every team directing them on how to

[27:41] roll this policy out for example is a

[27:43] really really great. Yeah,

[27:47] I love it. How about the rest of your

[27:49] company? like do you feel like you're

[27:52] able to like with AI do like like where

[27:56] is legal on AI compared with other other

[27:58] functions at the company and has it

[28:01] changed how you work either internally

[28:04] or with outside legal?

[28:05] Yeah, so other teams I don't they don't

[28:09] have that's not true. I was going to say

[28:11] they don't have like product specific

[28:13] tools but they actually do. So our

[28:14] product team has a tool for ENGE that's

[28:17] a that's an NGE specific tool similar to

[28:20] how GCAI is for legal. The rest of the

[28:22] team does generic um claude I believe

[28:26] and they especially over the past 6

[28:30] months to a year have have really used

[28:32] it a lot. Before that it wasn't that

[28:34] much which is interesting. So yeah, I

[28:37] was glad I could get ahead of it

[28:39] policy-wise and kind of be the

[28:41] spokesperson for AI whilst also handing

[28:44] over the policy with giving sort of

[28:46] guardrails on how to use it. Have you um

[28:48] how have you kept your policies a living

[28:50] document? Like we we had a great

[28:52] conversation with um TechGC or Luite on

[28:55] this around you know the the like

[28:57] capital P policy for AI you know that

[29:00] all of us came up with back in 24 is

[29:03] like kind of stale and doesn't account

[29:06] for agents and it doesn't account for

[29:08] MCP and all these other things.

[29:11] you know, somebody literally made a

[29:12] comment that I was like, "Oh, a policy.

[29:14] That's so quaint." And I was kind of,

[29:16] you know, I thought, "Okay, you know,

[29:17] like, all right, I criticism taken,

[29:19] point noted." Uh, so what are you what

[29:22] are you doing? Are you looking at it

[29:23] quarterly? Are you doing it case by case

[29:25] or anything you're doing to keep on the

[29:26] policy side to keep up with the rest of

[29:29] the business as they as they catch up on

[29:30] AI?

[29:31] Yeah, we have a policy. I'm sure no one

[29:33] has read it. So, and so what we do is I

[29:35] I work it into these legal presentations

[29:38] for each team. Also, in a few weeks in

[29:40] all hands, I'll give a refresher on hey,

[29:42] here's our and I make really simple

[29:44] guidelines on AI like super high level.

[29:46] Our guidelines are if it is already

[29:49] publicly accessible or you don't care if

[29:51] it is publicly accessible or gets in the

[29:53] hands of a bad actor, go wild. Don't

[29:55] care what you use. Don't care what you

[29:57] tool to tool it is. If those things are

[29:59] not true, it needs to go through legal.

[30:01] And for our current vetted tools, no

[30:05] personally identifiable or sensitive

[30:06] information goes into them. So it's like

[30:09] pretty I've tried to make it really

[30:11] simple for the team.

[30:12] Very simple. I love it. It's also, you

[30:14] know, to me it maps to the law, right?

[30:16] You know, when you think about these

[30:17] definition of trade secret, you kind of

[30:19] just explained it. I mean, it it's it's

[30:21] really that. And I always think of, you

[30:24] know, get talking about nerding out. I

[30:26] think of like, okay, you know, the

[30:28] famous case in Trade Secret that uh the

[30:31] shape of a shipping container. So,

[30:33] literally, you go to like the port of

[30:34] Oakland and you've got shipping

[30:35] containers. The shape of those,

[30:39] there was a famous case was like, "Oh,

[30:40] it's a trade secret." It's like, well,

[30:42] no, it's not. Walk up to the dang

[30:43] container and you can see it, you know,

[30:45] like literally like how it

[30:47] interconnects. And now, of course, you

[30:48] know, all of global commerce goes

[30:50] through these shipping containers that

[30:51] are of course interoperable and it's not

[30:53] a trade secret of whatever company came

[30:55] up with the original thing for that

[30:57] reason. So, yeah, I love that. I mean,

[30:58] it's also like, you know, I think we get

[31:01] we I've learned a lot from the security

[31:03] space of like, okay, if you want

[31:04] security policies that people follow,

[31:06] you got to make it easier for them to

[31:07] follow. And, you know, you want people

[31:09] don't inherently want to do the wrong

[31:11] thing. They generally want to do the

[31:12] right thing. It's just that they they

[31:14] you know I think a good policy makes it

[31:16] easy for them to do that.

[31:18] And I will I'll add one more thing to

[31:20] that is trying to explain the risk is

[31:22] really helpful to incentivize following

[31:25] policy. So I try to do that. It's a

[31:26] little more complicated.

[31:28] Yeah. So how do you do it? So so so

[31:29] we're in your we're in our presentation.

[31:30] We're watching what do I need to do? So

[31:32] so so put us in your presentation. What

[31:34] are you saying about risk?

[31:35] Yeah. So I typically this will be for

[31:38] the team specific presentations. So like

[31:40] if it's product design and engineering,

[31:43] the risk is that our intellectual

[31:46] property is no longer ours, right?

[31:49] Um and our product is is key. That's

[31:53] like

[31:55] really the IP. Yeah. Yeah. Yeah. It's

[31:57] interesting. We had something where I

[31:59] was always um I used to give the

[32:01] presentations on IP and trade secret

[32:03] when I was at Amazon.

[32:05] The um interesting example was like you

[32:08] know so Apple famously you know when you

[32:11] build on the Apple case if your name was

[32:13] not on the actual um header you had to

[32:15] say on your LinkedIn or whatever you had

[32:17] to say that you worked for a Certino

[32:18] based electronics company and it's like

[32:20] okay well maybe you can figure that out

[32:22] but no the uh the example that I used in

[32:26] those cases was that we had an intern in

[32:30] one of the groups that the intern's

[32:32] assignment for the summer was to figure

[32:34] out if a particular algorithm could be

[32:36] used to optimize something in the

[32:38] product. And it was not an easy answer.

[32:41] It was literally like whatever 10 weeks

[32:42] of work for this person to figure out.

[32:45] It turned out sadly the answer was no.

[32:47] You could not use that algorithm for

[32:48] whatever it was, you know, but that's

[32:51] still a trade secret because it's going

[32:53] to take company Y that's not your

[32:56] company 10 weeks to figure it out

[32:58] themselves. And so even though it wasn't

[33:01] even part of the product, that was the

[33:03] example that we used. And so it's nice

[33:05] to make it to to make it grounded. And

[33:07] also in your case, I'm hearing that

[33:09] you're making the training specific to

[33:11] the group of like what they care about.

[33:13] It's literally their livelihood, right?

[33:15] So making it real in that way. Um I I

[33:17] love that too. All right. Uh you said

[33:20] before that people should take what

[33:22] works for them in careers and leave the

[33:24] rest. It's, you know, I've also heard

[33:26] like the version of this advice that's

[33:29] given to founders is like know which

[33:32] investors advice to ignore. So I heard

[33:35] that too. How does that that show up?

[33:38] And when when did you get to that point

[33:39] in your career where you could know that

[33:41] you yourself had the judgment to be able

[33:44] to ignore some advice or some advice

[33:45] would be bad? So this came up even my

[33:49] first year of law school. This is a

[33:51] random funny story. I asked like a 2L or

[33:54] 3 L. I was reading his case and I was

[33:56] like, "How do you know like who's the

[33:58] appellent?"

[34:00] And this like 2L or 3L, whatever they

[34:02] were, it's like, "Oh yeah, appellent is

[34:04] always a plaintiff." And I was like,

[34:06] "Okay, okay." And then very quickly I

[34:08] realized that is just not objectively

[34:10] false. Like, right, what? And I think I

[34:14] mean throughout law school I was always

[34:16] and even even in my early years of my

[34:19] career I was really like I was doing a

[34:21] lot of informational interviews and

[34:22] trying to get input and advice from

[34:24] people who were doing what I wanted to

[34:25] do or who had you know established

[34:27] careers and everyone wants to give their

[34:30] advice and opinion as if it's like the

[34:33] truth right because it is the truth for

[34:35] them but then in I want to say three

[34:37] four past three or four years

[34:40] it's become so clear clear to me that

[34:43] that's their advice, right, for their

[34:44] career and their specific set of

[34:46] circumstances. And that really might not

[34:49] be the case for everyone that it's not

[34:51] it's not necessarily applicable to

[34:53] everyone. So, I think and this even goes

[34:55] beyond law, right? There's this whole

[34:57] like personal development world out

[34:59] there and everyone talks as if their

[35:02] opinion is like this is the thing that

[35:04] will save everything and make everything

[35:06] better. And that's just that's what

[35:08] worked for them and it shouldn't be

[35:10] taken as like capital T truth ever. Um

[35:14] I love that it was it was a journey for

[35:16] me to realize that too and you know

[35:18] there's a flavor too that's like they're

[35:20] trying to sell a book or trying to

[35:21] whatever and everybody has their own

[35:23] point of view. So it got to the point

[35:24] where one of my favorite investors said

[35:26] or you know there was a podcast with the

[35:27] CPO of Ripling on Lenny's podcast super

[35:30] popular and he basically said there is

[35:32] no advice there's just here's what I've

[35:35] experienced and extrapolate that from

[35:37] what you will because of course things

[35:39] are different like we deal with this now

[35:40] where you know GCI our growth and the

[35:43] kind of startup journey is really really

[35:45] high you know but that's in a new era of

[35:48] AI so if you compare us with other AI

[35:51] companies it's still high but it's not

[35:53] crazy high and it's like okay we can we

[35:54] need to be benchmarking against the best

[35:56] and doing this kind of situation

[35:57] specific advice that appellent story

[36:00] though that that one takes the cake it's

[36:01] always a play so good today is February

[36:04] now and it's a perfect February where uh

[36:06] let's see what is it so the the dates on

[36:08] the calendar all match up to calendar

[36:10] dates and there was a tweet that was

[36:12] like this hasn't happened in 854 years

[36:15] and I read that and I was like oh wow

[36:16] that's so interesting and then my

[36:18] husband's like no actually it's like

[36:19] every whatever seven years 7.5 because

[36:23] of the leap year, but like this is not

[36:25] like, you know, like you're so dumb.

[36:27] Anyways, uh I I I agree with that, but I

[36:30] kudos to you for for having the gumption

[36:33] and and realizing it. Uh the wider

[36:35] point, if somebody listened to this

[36:37] episode and want to understand how you

[36:40] operate, what would you what would you

[36:41] tell them?

[36:43] Um people first. I really spend a lot of

[36:47] time vetting, interviewing,

[36:50] training, making people feel like I care

[36:55] and I want to mentor them and train them

[36:57] and that we're a team. And also, yeah,

[37:00] the trust within the rest of the company

[37:02] is really important. Um, the other thing

[37:04] is I'm really kind of obsessed with with

[37:08] results, like business centric results

[37:11] and how can we continue to add value and

[37:14] be a thought partner to get those

[37:16] results

[37:18] and just keep getting better and better.

[37:20] I think it's the name of the game is

[37:22] like how can I keep growing as a leader,

[37:25] as a person that that creates

[37:27] fulfillment in good teams.

[37:30] I love that. I mean the curiosity point

[37:32] and then the one of our GCI principles

[37:34] is 1% better every day and of course you

[37:37] know that the book talked about the

[37:38] atomic habit books talks about is

[37:40] compounding right so it's like 38 times

[37:42] better in a year so I love that um all

[37:45] right so on the topic of books in the

[37:47] lightning round what's a book idea or

[37:49] mentor that has shaped how you lead I

[37:52] have two mentors I don't that so and I

[37:56] have more than this right but for

[37:57] listeners they're very accessible tar

[37:59] brock t a R A B Broch is how you B R A C

[38:02] is how you spell it. Mindfulness

[38:04] meditation teacher. She's fantastic.

[38:08] I think being an awesome leader starts

[38:10] with yourself, right? And your own

[38:12] personal universe. Tony Robbins has been

[38:17] like his he has his rapid planning

[38:18] method is fantastic. He he has some

[38:20] really good as like kind of cheesy as

[38:22] like some of his, you know, oneliners

[38:25] might sound, he has some really great

[38:28] tactical tools. What's a myth about

[38:30] being a general counsel or or running

[38:34] compliance

[38:35] that you would debunk or that that you

[38:38] think people believe that is not true?

[38:40] I don't know if people think this, but I

[38:41] think often

[38:43] people think you have to know everything

[38:45] about everything. Like I am a true

[38:47] generalist, but I don't know everything

[38:49] about everything. Like you need to know

[38:51] when to outsource to outside counsel,

[38:54] right? You need to know what you know

[38:55] and where the limit is and what's

[38:56] important enough to outsource. And um of

[39:01] everything you've achieved, you're very

[39:02] accomplished. I'm gonna I'm gonna take a

[39:04] question from how I built this cuz

[39:05] somebody said we're how I built this for

[39:06] legal. How much of it has been luck

[39:09] versus hard work?

[39:11] Some of it's certainly luck. I'm I'm

[39:13] playing percentage wise. If we say how

[39:14] much of it is hard work, it's a lot. But

[39:17] it's not just my hard work, right? I

[39:19] work hard, but there's so many other I

[39:21] mean, I was just thinking the other day

[39:22] of like all the people whose whose

[39:24] shoulders I stand on, who built the

[39:27] world we live in today where like I as a

[39:29] woman, etc., etc., can like do what I'm

[39:31] doing. So, it's I don't know. I'm going

[39:33] to give it 60% hard work, not just me,

[39:35] but a gajillion other people who like

[39:36] created the universe that allows me to

[39:38] do this.

[39:41] And and 40% Yeah, pure luck for sure.

[39:44] I love it. I love it. Any closing

[39:48] thoughts you want to leave listeners

[39:49] with?

[39:50] You create your own reality. You can

[39:53] create your own the legal function that

[39:55] you want. You can create the own career

[39:57] you want. Sky's the limit. Think about

[40:00] it. Write it down. Make it happen. You

[40:02] can do it.

[40:03] Love that. Thank you so much for joining

[40:06] and sharing your perspective, Elana.

[40:08] Thank you. That was my conversation with

[40:10] Elana Freeman, the head of legal and

[40:12] compliance at Swing Education and a

[40:14] leader that brings clarity and joy to

[40:16] how legal operates today. Follow CZ and

[40:19] friends wherever you get your podcasts.

[40:21] To learn how legal teams are using AI to

[40:23] work smarter, lead with impact, and

[40:26] reach the sky's the limit, visit gc.ai.

[40:29] Thank you for listening. We'll see you

[40:30] next time.