From Prosecuting to Leading In-house at a Tech Startup: S. Michael Lee, GC & COO at Engaging.ai

Introduction: 0:00

• Introducing S. Michael Lee, General Counsel & COO at Engaging.ai, a generative AI/UX engine for creating multimedia experiences without any code.
• Serving as counsel at many companies and law firms, including a role as GC at Blind, a platform that allows employees to anonymously share information with one another.
• Spending 18 years as a prosecutor and regulator in the Santa Clara County District Attorney’s Office.

Honouring your connection to the Korean American community: 2:40

• Viewing the United States as a mosaic, rather than a melting pot.
• Working for a dry cleaner until your boss compels you to enter law school.

Finding inspiration in your community to work in public service as a prosecutor: 5:36

• Looking to Hawaiian Japanese Americans for a model of how to integrate into American society.
• Combating unconscious bias as the first Korean-American prosecutor in Santa Clara County.
• Subverting the stereotype of the “angry Asian man” to persuade biased juries.
• Taking negativity and reversing it as a force for good.

Applying lessons learned as a prosecutor to the private sector: 11:36

• Comparing the responsibilities of a trial attorney to the role of GC at a small company.
• Working as a jack of all trades to achieve your goals.

Finding an in-house role after building your career in public service: 12:57

• Being met with confusion by people who don’t understand your interest in switching industries.
• Framing your work in consumer protection as regulatory experience.

Advice to lawyers in government service trying to move into the private sector: 14:37

• Building experience in various industries to receive training and learn what you like and are capable of doing.
• Trying everything and taking every available opportunity to get trained in a new field.

Networking to advance your career: 16:57

• Finding half of your jobs through introduction.
• Maintaining a reputation as reliable so people hire you or share your information with others.

Dealing with layoffs at Blind: 20:40

• Reaching out to your network and being honest with your network about your need for a new role.
• Eroding the stigma surrounding layoffs in the tech industry.

Taking on a new GC and COO role at Engaging.ai: 25:04

• Dealing with the excitement and challenges of the startup environment. 
• Prioritizing creativity and flexibility in complicated and unique situations.

Advice to lawyers looking for new positions: 26:52

• Refusing to limit yourself or impose glass ceilings on your career.
• Taking on roles even if you don’t think you’re 100% ready for them.

Book recommendation: 28:19

• The Bobiverse series by Dennis E. Tyler

What you wish you’d known as a young lawyer: 29:02

• Not assuming you know where your career will be decades in the future.
• Understanding that every new experience is preparation for the next thing.

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