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March 4, 2021

TripActions General Counsel Sai Jahann on Leadership, Mentorship & Community

Samantha Shankman
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News
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What does it take to guide a high-growth startup through a myriad of changing government regulations and rules? TripActions General Counsel Sai Jahann knows better than most as the lawyer charged with interpreting and working with the government and unexpected travel requirements throughout 2020. With a combination of grit, drive, and teamwork, Sai led the TripActions legal team and organization throughout its challenges and now into its biggest opportunities.

Sai joined TripActions three years ago and has played an integral role in its rapid growth during that time. Sai recently sat down with TripActions Head of Diversity, Equality & Inclusion Shaka Senghor to share more about her background, motivation, and approach to leadership in this chapter of the Insights at TA series.

Shaka has interviewed and has been interviewed by leaders across all industries and walks of life including Oprah, Ben Horowitz, and Jordan Harbinger. He digs deep into the unexpected events that impact leaders’ lives and their approach to team building, innovation, and success.

The conversation begins with Sai’s journey to becoming a lawyer. Although she jokes that her options were limited to doctor or engineer (and she does have her bachelor’s degree in biomedical engineering), she realized her passion to study law while in her first job at the Open Society Foundation in New York.

“I worked with a lot of amazing attorneys that worked on human rights issues and doing international advocacy work. I admired them and the way that they thought, approached problems, and articulated themselves in a meaningful clear way. So I did what they did and went to law school,” explains Sai who later graduated from Stanford Law School.

Sai and Shaka then explored the evolving role of corporate lawyers and how their position has become even more important in a changing, dynamic social climate.

Sai leads a team of lawyers at TripActions, but is a mentor to many throughout the organization. In the interview, she talks about the importance of having female mentors as she built her own career and how that in turn has helped her become a better, more involved leader.

“I think it’s important for people to have peers, mentors, and mentees that get your perspective, because you need that comfort. But you also need people that come from a completely different perspective because that’s what helps you identify your own blind spots and grow as a holistic person. It has to go in all directions,” said Sai.

“Mentorship is especially important in tech because you don’t get the professional training in tech that you would in a law firm or accounting firm or consultancy. We don’t have a set of super rigid progression pathways. Tech is so flat and non-hierarchical that it gives people a lot more room to maneuver and let merit drive their career very quickly, but it also means that you don’t have the benefit of any of those structures that actually teach you how you write an email to someone senior or how to navigate certain situations. I find that this kind of informal mentorship becomes even more important in the tech industry, because there’s a set of professional skills that you don’t get in tech unless people go out of their way to teach you or you go out of your way to teach yourself,” she said.

To learn more about Sai’s role not only as TripActions’ legal counsel, but a leader and mentor to many, watch the video above. We’ll continue sharing insights from TripActions leaders each month so check back for more Insight Videos with Shaka Senghor.

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