Why Your Legal Team Needs an AI Hackathon (Dina Segal - CLO Gusto)

In this episode, Dina Segal, Chief Legal Officer at Gusto, talks about her transition from private practice to leading an in-house legal and compliance department. The discussion covers Gusto's mission to support small businesses with payroll, benefits, and HR compliance. Dina outlines the strategic advantages of product counseling for in-house attorneys and details how Gusto's legal team actively integrates artificial intelligence into its daily operations. Key topics include organizing legal hackathons to build automated solutions, managing agentic workflows with human-in-the-loop accountability, and updating hiring practices to prioritize a learning mindset and technological proficiency in modern legal professionals.

Things We Talk About in this Episode

• Roots in Law and Business: Dina shares how her grandfather's legal practice in Ukraine and her father's experience as a small business owner inspired her legal career.

• Overview of Gusto: A breakdown of how Gusto assists small businesses with payroll, HR, and navigating complex regulatory compliance.

• Transitioning In-House: Dina discusses her move from Big Law (Winston & Strawn) to in-house roles at Renovate America, Intuit, and eventually Gusto.

• The Value of Product Counseling: Why getting involved in product counseling is highly recommended for attorneys looking to build trust with business teams and understand commercial objectives.

• Legal Department Hackathons: How Gusto's legal and compliance team uses internal hackathons to identify operational bottlenecks and build targeted solutions using enterprise AI.

• Successful AI Workflows: Examples of processes automated by the legal team, including rate change management, commercial contract review, and licensing compliance.

• Deploying Agentic AI and Accountability: The framework Gusto uses to evaluate AI tools before they go live, focusing on problem identification, compliance risk controls, and maintaining human-in-the-loop oversight.

• Hiring for AI Proficiency: How Gusto has restructured legal job descriptions and interview processes to screen for a strong learning mindset and systems-building capabilities.

• Advice for New Lawyers: Practical guidance for law students and young attorneys on navigating the evolving, tech-driven legal landscape and the importance of finding strong mentors.

Episode Credits

Editing and Production: Grant Blackstock

Theme Music: Home Base (Instrumental Version) by TA2MI