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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