Introduction 00:05

• Introducing Mark Kahn, Partner and Head of Consumer at Protégé Search, and a GC-turned-Exec Recruiter.

Starting your career in product with your dream organization: 1:22 

• Taking your first job working with a baseball team, the Oakland A’s.
• Getting close enough to the business that you are asked to weigh in on signing Jose Conseco.
• Returning to school and marrying your tech degree with your law degree.
• Dealing with job search during the 2000 dot-com-bubble burst.
• Diverting plans to work in tech and becoming a litigator.

Working your way up the corporate food chain to WhatsApp: 6:22

• Dealing with imposter syndrome and finding disappointment in your work.
• Reeling what aspects of your work you don’t like and gravitating towards your strengths.
• Identifying the right-sized company regardless of role and realizing you work best in start-ups.
• Reconsidering an opportunity at WhatsApp after the Facebook acquisition announcement.

How WhatsApp differed from his expectations: 12:39

• Taking on an international role.
• Repositioning your organization to engage with governments and corporations.
• Protecting user privacy alongside concerns from law enforcement.

Knowing when to step back from a stressful role and leave: 18:27

• Surviving a stressful and high-profile position.
• Recognizing when you aren’t being an effective team leader.
• Prioritizing your health and mental state when your performance suffers.

Taking time off and negotiating a role at Segment: 24:13

• Finding time to evaluate whether you still want to work in legal.
• Using time between jobs to better yourself and try new things.
• Approaching a new opportunity at Segment with your strengths in mind.
• Meeting with recruiters who understand your concerns.

Working with an executive coach: 29:13

• Finding useful advice even if you can’t build rapport.

The Segment/Twilio acquisition and carving out a new role for “VP of Ethical Use”: 30:13

• Defining the idea of “ethical use” for product users.
• Twilio’s questioning of the Parlor app following its role in the January 6th riots.
• Developing an ethical framework for acceptable use.
• Heading a committee to evaluate hypothetical examples of acceptable use.

Stepping away from law into executive recruiter role: 38:15

• Choosing to leave a role that is interesting but not essential.
• Shifting your focus to help others build their careers.

Demystifying the job-seeking experience: 40:29

• Offering tips to those looking for new executive roles.

“Designing Your Life” and advice to his younger self: 43:23

• Recommending a book to help readers understand their working goals.
• Wishing you had been better prepared for unanticipated challenges.