Ashianna Esmail Enhances Innovation at Flexport with Law

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As Ashianna Esmail strolls down the long stretch of Market Street that bisects downtown San Francisco, she sees more than the eBikes, cable cars, sidewalk cafes, and street performers. Waymo’s self-driving cars navigate through traffic as local gourmands effortlessly order meal delivery with apps like GrubHub and Uber Eats. Coders sit nearby, sipping cold brew while working remotely on the latest advancements in augmented reality and artificial intelligence.

Even the Bay Area Rapid Transit system shows off its mastery of modern technology through an app loaded with real-time tracking, contactless parking payment, fare calculators, and personalized navigation options. While most people give credit for the region’s spirit of innovation to its robust community of programmers and developers, Esmail knows that the in-house legal and compliance teams working behind the scenes play a critical role behind their public success.

Esmail serves as executive vice president and chief legal officer and corporate secretary at Flexport, a supply chain company with a platform designed to help users optimize workflows and coordinate global logistics to bring products from the factory to the consumer. Each individual on her team of thirty professionals leaves an indelible mark on the overall organization. “The attorneys and risk professionals in legal and compliance each have unique skills that we bring to partner with the business so we can get creative and solve problems together,” she explains. “Innovation comes from legal and compliance, and not just from the technologists in Silicon Valley.”

The California native completed her undergraduate studies at UC Berkeley and headed to the nation’s capital to work for a non-governmental organization (NGO) dedicated to influencing humanitarian policies related to relations between the United States and Iraq. Esmail frequently observed conversations between lobbyists, lawmakers, and other stakeholders. As she listened, she noticed something: the creative minds driving collaboration and finding new solutions to driving legislative change had one thing in common—they all had law degrees. She enrolled to study at the University of Michigan Law School.

“The best idea in the room wins here, no matter who it comes from.”

Ashianna Esmail

By the time graduation came, Esmail had solidified her desire to work with mission-driven organizations where she would have the chance to make a true impact. Four years at Latham & Watkins helped her hone general problem-solving and critical thinking skills before she made the transition to an in-house role.

Esmail worked first in international payments through positions with Xoom and PayPal. She left the online payment platform in 2017 to join Flexport and work in international trade. Since her arrival nearly seven years ago, Esmail has focused on elevating the company’s legal and compliance functions. As CLO, she is also responsible for Flexport’s physical security team.

While those matters are of critical importance, Esmail is careful to ensure all she does ties back to Flexport’s overall mission. “We exist to make worldwide trade easier for everyone so companies big and small can all participate in global commerce,” she says.

That mission drives Flexport, and the company has been growing. When Esmail joined, she was one of about 200 employees. Flexport’s workforce has now surpassed 2,000. The company has also expanded its geographical footprint and reached past its core business of international cargo movement to build out customs brokerage services, last mile capabilities, trade financing, insurance, and more.

“Innovation comes from legal and compliance, and not just from the technologists in Silicon Valley.”

Ashianna Esmail

Esmail has kept legal at the center of this growth by ensuring her department serves as a strategic thought partner to the business. In heavily licensed and regulated industries, Flexport relies on legal and compliance to create the right infrastructure on which it can build each business line.

A simple credo helps Esmail get the best results. “The best idea in the room wins here, no matter who it comes from,” she says. Within Flexport’s legal and compliance departments, a strong work product is seen as table stakes, and each member of the team is committed to understanding how they can help both one another and the business grow in lockstep.

Esmail has been afforded the opportunity to build her own department, which she has customized to match Flexport’s needs. “We’re a company that has expanded into multiple businesses since my arrival, so each member of legal and compliance has to have deep subject-matter expertise in at least one area while developing the agility to support new business lines or innovative ideas,” she says. 

Those novel ideas sometimes transcend Flexport’s core business. About seven years ago, several of Esmail’s colleagues started talking about an emerging issue. They realized that the logistic and material aid meant for refugees, the unhoused, and those affected by natural disasters doesn’t always reach their intended destination. The problem often arises when people and groups lack access to the supply chain. In response, Flexport started a pilot program to identify and remove barriers that prevent the flow of resources.

Members of Flexport legal helped formalize the necessary partnerships and now support a full team that coordinates these efforts through Flexport.org. The group has worked with partners like UNICEF and Save the Children to complete nearly two thousand shipments that address the COVID-19 pandemic, the Ukraine conflict, and the Horn of Africa food crisis. These activities have impacted 112 million people in 78 countries since 2018.

There was a time when Esmail thought she needed to be crafting laws on Capitol Hill in order to drive impact with her legal degree. Now, she tells new attorneys to keep an open mind. “Lawyers are some of the most creative minds in companies, trained to solve problems. It’s possible to have a fulfilling legal career in many different arenas, including in the heart of Silicon Valley where you can be an integral part of driving the most innovative technological solutions to worldwide issues faced by real people every day,” she says.

As Flexport and Flexport.org move forward, Esmail will continue to partner with the business leaders and technologists to drive innovation.

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