Elana Freeman needed to get a meeting with the Chicago Teachers Pension Fund (CTPF). As Swing Education’s new compliance manager, Elana was aware that certain educational institutions were required to contribute to the fund, but CTPF wasn’t answering her calls. So she showed up at the building, asked to speak with someone, and walked out an hour later with everything she needed.
It turned out Swing Education didn't even need to contribute, but the experience taught her a valuable lesson: skip the friction, and go straight to the source.
Elana is now Head of Legal and Compliance at Swing, an ed tech company connecting schools with substitute teachers across seven states. She joined in 2019 when the company only had 40 employees and built the legal function from scratch. Today, Elana leads a two-person team that saves 40-plus hours a week with AI, advises on employment across states and two different business models, and has become the kind of legal partner that stakeholders are excited to work with.
"Great leadership is not about control,” she said. “It's about creating the conditions so good decisions happen consistently and quickly."
In this conversation, Elana and GC AI founder Cecilia Ziniti discuss building user and stakeholder trust, staying nimble in messy regulatory environments, and how AI has supercharged her legal team’s weekly output.
Building Trust Across a Distributed Team
When Swing was a 40-person company and everyone worked in-office, trust between legal and the rest of the business was organic. Everyone knew each other. Then the company scaled and went fully remote. New employees came in with preconceived notions about lawyers, and the organic trust in Elana’s department didn't automatically transfer.
Elana recognized that she needed to build trust organically and deliberately. The mechanism she chose was a series of presentations with every team across the company to show them who legal was, what risks their specific team faced, and how legal could help them be more successful.
"We are not telling you yes or no. We are working together,” she said. “You know the business outcome, you know what your team does best. We need to work together to make sure we're mitigating appropriate risk. And some risk is really okay to let go."
The presentations also served a second purpose: issue spotting. When every team in the company understands what legal is paying attention to and why, they start flagging things earlier. Problems that used to arrive on Elana's desk fully formed, already expensive, and already complicated, started arriving when there was still time to shape them.
Note from CZ: The idea of a legal presentation for each department is one of the most practical trust-building tools we’ve heard on this show. Rather than waiting for people to come to her, Elana went to every team in the company to brainstorm how they could work better together. That proactive move changed the entire dynamic between legal and the rest of the company.
The Value of Systems in a Chaotic Regulatory Environment
Swing Education operates in seven states and has two very different business models. In some states it runs a gig economy platform where substitute teachers are categorized as independent contractors. In California Swing operates a full employment model, which means abiding by California’s wage and hour law, non-exempt employee requirements, and penalty exposure.
Compliance for a company with this much regulation is a massive undertaking. Substitute teacher certifications and background check requirements vary by state, and sometimes by school district. On top of that, schools can add their own requirements for substitutes. And any time the company wants to expand, there are new compliance requirements and additional legal exposure.
Elana makes it work by doing what she did with the CTPF: go directly to the source, know the requirements well enough to know when the answer you're getting is wrong, and build the infrastructure as you go to make the next state easier.
Systemizing compliance allows Swing’s legal team to flag issues in the moment, rather than catching them after they’ve become liabilities. For example, when the Swing CEO floated the idea of switching from weekly to daily pay for California employees, a seemingly employee-friendly move, Elana came back with hard numbers.
"In California, if we switch from weekly pay to daily pay for hourly non-exempt employees, our potential liability goes up by 7x,” she told him.
Rather than saying no outright, Elana explained the risk and allowed the executive team to decide whether the benefits outweighed the risk.
"I consistently message everything as risk reward benefit: weighing risk and reward. If the reward outweighs the risk, we do it. I understand risk, you understand reward. I can put a dollar value to risk and we can literally just weigh them."
Elana builds cross-functional trust by positioning her department as the one that makes sure the business knows exactly what it is signing up for before it makes a risky move, and it’s paid off.
How Lean Teams Can Increase Efficiency
Elana describes herself as “obsessed with efficiency,” but she means that differently than most business leaders.
Efficiency for a two-person legal team is about being ruthlessly clear on which risks deserve the team's full attention, which deserve partial attention, and which are simply not worth the effort. Every issue brought to Legal gets triaged before it gets worked. The triage is the work, and it’s saved them a lot of weekends in the office.
The management technique she uses is simple: every time her associate brings her a project or an issue, she asks the same three questions:
What is the goal?
What is the outcome?
What is the impact?
"Getting really clear on what are our highest risks that we really need to dot our I's and cross our T's on, what are the medium ones we want to mitigate, and what are the ones that are just not super risky and aren't worth the effort – that is what efficiency means,” she said.
This practice has become so ingrained into her team culture, that now Elana’s colleague comes to her with the analysis already finished. This extra step means Swing’s legal team can avoid absorbing additional problems and focus on the business priorities.
How Swing Went from No AI to Saving 40 Hours a Week
Two years ago, Elana walked into a product team presentation and asked who in the room was using AI. Nobody raised their hands. She advised them, as their lawyer, that they needed to be.
Because Elana was ahead of the curve, Swing’s AI integration was smooth and successful. Swing Education uses automation extensively, and legal AI saves Elana's two-person team 40-plus hours a week. Her colleague Jacob experiments with new use cases and reports back on what is working.
"It can be easy to learn five ways to use AI and just keep using it in those five ways,” Elana said. “But expanding it to write me this policy, but also write me a playbook for how to roll it out, and write me communications to every team, is really powerful."
Elana’s team succeeded by building their AI policy first, explaining the risk in terms each team could understand, and becoming AI’s biggest in-house advocates. The usage policy is straightforward: use good judgement and assume anything fed to AI will become public.
"Our guidelines are: if it is already publicly accessible or you don't care if it gets in the hands of a bad actor, go wild,” she said. “If those things are not true, it needs to go through legal. I've tried to make it really simple for the team."
Swing’s AI policy is almost exactly how trade secret law works: if it is publicly accessible, it is not a trade secret. Making the policy match the underlying legal principle makes it easy for everyone to follow it.
On the legal side, AI has completely changed how Elana’s team operates. They now use legal AI to summarize documents, rework communications, sanity-check employment law analysis, and draft policies and the rollout playbooks in a fraction of the time it used to take. These days the team saves, on average, 40 hours a week by utilizing legal AI and continually expanding their use cases.
Elana offers one caveat, however: for the genuinely in-the-weeds employment law questions, AI gives a useful gut check but sometimes gets it wrong in ways that only become visible if you already know enough to spot the error. The tool accelerates the work of someone who has the underlying knowledge, but it does not replace that knowledge.
In closing, she advises in-house lawyers to take what applies, leave the rest, and build the function that fits your company.
"You create your own reality. You can create the legal function that you want,” Elana said. “You can create the career you want. Sky's the limit. Think about it, write it down, make it happen."
The legal teams that are following Swing Education’s example by leaning into AI and designing smart usage policies are the teams that will thrive in whatever comes next. GC AI is built to give those teams the leverage they need to do it. If you're ready to find out what 40 hours a week back actually feels like, try the best legal AI on the market for free.
