Alex Kiles – Airbnb

Senior counsel steers Airbnb through data-driven policymaking

When Alex Kiles joined Airbnb as its policy senior counsel, he knew all about policymaking, having worked on both the House and Senate sides of the Hill. But he hadn’t yet learned all he needed to know.

That’s because that was federal policymaking, and state and local policies regulate short-term rentals.

“There were two big gaps of experience,” Kiles recalls. “I knew nothing about short-term rental policy—I had stayed in Airbnbs, but I knew nothing about the intricacies of zoning and land use laws and how this business area is regulated. And second, state and local policymaking is so different from federal policymaking; things tend to move really fast.”

Alex Kiles | Policy Senior Counsel | Airbnb

Alex Kiles | Policy Senior Counsel | Airbnb | Photo Credit: Derrick Creative

So, Kiles studied the relevant law and learned how that law is forged and changed, which happens quickly and differs from city to city and state to state. It was a crash course in short-term housing policy, and Kiles aced it thanks to his co-workers. By building good relationships with colleagues who had been around longer, he managed to pick up what he needed to know.

Kiles, who has represented Guantanamo detainees, other technology companies and the government of Ukraine, says jumping into unfamiliar terrain has been a constant in his career. Today, he has mastered the demands of his job, and he’s enjoying the role.

“Airbnb is an incredible place to work; the company stands for building connection and belonging around the world,” he says. “It’s about this idea of creating meaningful experiences for people visiting new communities.”

Drawing on data to drive policymaking

Kiles has sometimes encountered cities that are contemplating short-term housing bans, and in those cases, he works with policymakers to craft a solution that supports Airbnb hosts and addresses policymakers’ concerns. He says local officials often respond to feedback from key stakeholders—be it neighboring homeowners, small business owners or people trying to make some extra money to pay their mortgages.

Each jurisdiction is unique in how they craft short-term rental policies.  For example, he says, in certain areas of the country, there’s an emphasis on private property rights, so hosts advocate for the rights of homeowners. In other areas, particularly cities, there are concerns about housing supply, so Kiles works with those cities on regulations that allow Airbnb to operate there while mitigating concerns about outside investors buying up local housing stock to use for short-term rentals.

Alex Kiles | Policy Senior Counsel | Airbnb

Through it all, Kiles has adopted a data-driven approach to policy advocacy. He likes to cite studies—for example, one commissioned by a Texas city that showed that once the city allowed short-term rentals, there was no measurable increase in nuisance complaints among those spaces compared to other homes.

Lately, Kiles has been supporting his colleagues in reinventing the private room model, hammering out short-term rental policies in the southeastern third of the U.S. and Canada.

Airbnb recently launched an updated version of that model in May called “Rooms,” a dedicated category of private rooms offering guests a more affordable way to rent part of a house. But the updated version also takes consumer concerns into account, from providing more information on private room hosts to enhancing Airbnb’s safety features.

For his part, Kiles has been drawing on his knowledge of the public policy issues at play to highlight the value short-term rentals bring to a city. He says his goal is always to carve out a win-win.

From the Hill to City Hall

After receiving his bachelor’s degree from Washington University, Kiles earned his J.D. from the University of Chicago in 2014. He started his career as an associate at Covington & Burling, where he also summered in 2013.

One of his first cases there required traveling to Cuba to represent Yemeni men who had been detained at Guantanamo for 14 years without charges—an experience that, Kiles says, had “a profound effect” on him. He also worked on a team representing Ukraine against Russia before an international tribunal concerning the annexation of Crimea.

In 2016, Kiles departed Covington to clerk for Judge Emmet Sullivan of the U.S. District Court, District of Columbia—he calls the experience with Sullivan “incredibly transformative and key to shaping my personal view of justice”—before returning to the law firm in 2017. In 2019, he joined the House Committee on Oversight and Reform as counsel and then served on the House Select Subcommittee on the Coronavirus Crisis. In 2021, he joined the Senate Commerce Committee as counsel and policy advisor. He assumed his current role at Airbnb in 2022.

Alex Kiles | Policy Senior Counsel | Airbnb

While serving in the House, Kiles worked for the late Rep. Elijah Cummings (D-MD), who chaired the Oversight Committee and passed away in 2019 at age 68.

“He was an example of what a dedicated and compassionate public servant can be,” Kiles says. “Chairman Cummings wanted to make the country a better place not just for his constituents, but for the entire country—it was just truly inspiring.”

Today, Kiles says he’s grateful to have found a company with a mission he believes in and a role whose demands align with his skillset.

“I’ve enjoyed learning how the country works,” he says. “I’ve been fortunate to witness federal policymaking on the Hill, but now I have an opportunity also to see state and local governments in action, where a lot of critically important policy is made—and understanding how that works, too, has given me a more cohesive view of our democracy.”

View this feature in the Vanguard Fall II 2023 Edition here.

Published on: August 30, 2023



Showcase your feature on your website with a custom “As Featured in Vanguard” badge that links directly to your article!

Copy and paste this script into your page coding (ideally right before the closing tag) where you want to display our review banner.


I was honored to be the subject of an article. I enjoy reading Vanguard articles and seeing how other attorneys got to their positions and see their jobs. It's also interesting to see how different law firms partner with the subjects of the articles.
– Henry Marquard, in-house counsel, Stanley Consultants Inc.
As promised in advance, my feature in Vanguard has increased my visibility within the profession and prompted more than a few people I have not communicated with recently to reconnect. One of the Italian law firms I have used in the past is now in the process of interviewing me for an article on their website and tweeting out the feature story. Activity and the number of people connecting with me on LinkedIn has soared, which is great. The Vanguard writers and editorial staff were great to work with—highly professional and made the effort to make the experience both fun and rewarding (they were also respectful of the time pressures and demands all lawyers face). I was very pleased with the experience and the final outcome. Needless to say, I have been very pleased. All in all working with Vanguard has been a very positive experience which generated good publicity for both Shawcor and myself. My sincere thanks.
– Tim Hutzul, General Counsel, ShawCor Ltd.
The piece highlighting my company, Bob Baker Enterprises, Inc., came out fabulous. Our company is in the new and used car sales and service industry. Everyone was great to work with and extremely professional. They produced a high-quality product and have provided expert assistance and guidance post-production of the article.
– Wade Poulson, General Counsel, Bob Baker Enterprises Inc.
It was a great honor to be featured in Vanguard Law. Working with every member of the team, from the initial interview with Erin Clark, through production with Victor Martins, writing the article with Taryn Plumb and creating the final content with Dave Gushee, was a true pleasure. Everyone was very professional, enthusiastic and supportive, and their creative approach and positive attitude clearly came through in the final product.
– Kevin C. Rakowski, Senior Vice President, Deputy General Counsel, Compliance with Radian Group Inc.


Spring I 2024



  • * We’ll never share your email or info with anyone.
  • This field is for validation purposes and should be left unchanged.