Join Rob Chesnut, author of Intentional Integrity: How Smart Companies Can Lead an Ethical Revolution, as he discusses his time as a prosecutor at the Department of Justice and his tenure as Chief Ethics Officer at Airbnb and SVP of Trust and Safety at eBay shaped his groundbreaking approach to integrity and company culture.

‍

Key Insights

‍

1. From Prosecutor to Builder: Why Positivity Matters

After years at the DOJ, Rob left prosecution because “you’re always coming in at the end of a troubled life.” He wanted to build, not punish. That led him to eBay, where he helped create one of the first trust and safety teams in tech. “We were making the internet safer, and that felt good,” he says — proof that ethics and innovation can grow together.

‍

2. Integrity Is the New Compliance

At Airbnb, Rob saw that traditional compliance checklists didn’t inspire people. “Nobody reads a code of conduct they just clicked through,” he says. His answer: teach integrity, not rules. He reframed compliance as storytelling — short, funny 5-minute videos featuring company leaders — and participation skyrocketed. “Leaders are the carriers. Integrity is contagious.”

‍

3. How Airbnb Made Ethics a Cultural Habit

After Uber’s 2017 crisis, Rob and CEO Brian Chesky asked: “How do you drive integrity into the culture?” They built a voluntary Ethics Advisor program — appointing respected employees in every region as go-to integrity voices. Within a year, these advisors became the top source of ethics questions. “People won’t go to Legal,” Rob explains. “But they’ll walk over to a peer’s desk and ask quietly.”

‍

4. Why Legal Must Own the People, Not the Policy

Asked about his proudest legacy at Airbnb, Rob doesn’t cite projects. “If it’s about an individual accomplishment, it won’t last. My legacy is the people.” His north star as GC was to hire leaders who could scale culture, not just compliance. Many of those regional GCs still lead at Airbnb today.

‍

5. The Five-Year Rule: Keep Learning

Rob says his career runs in “five-year cycles.” Every five years, he changes roles to re-enter discomfort. “Growth happens when you don’t know what you’re doing.” It’s how he evolved from prosecutor → eBay exec → GC → ethics leader → author — each time reinventing his toolkit, not his values.

‍

6. Closing Insight

“Compliance tells people what not to do. Integrity shows them who they are.”

For General Counsels navigating rapid growth and public scrutiny, Rob Chesnut’s message is clear: you can’t outsource culture to HR — it starts in Legal.

‍

‍