Angela Chadwick – Wing

Much as she enjoys living and working in Northern California, there are times when Angela Chadwick envies those in the western Virginia town of Christiansburg. Other times, she feels the same about those in metro Dallas/Fort Worth.

Angela Chadwick | Wing | General Counsel

“I don’t cook and don’t like leaving home to shop for what can be delivered,” she says. “I also like to have my things delivered fast.”

Should Christiansburg dwellers crave a Wendy’s combo complete with a Frosty, they can have it delivered by drone to their doorstep in as little as 15 minutes through the DoorDash app. Should Dallas residents within a six-mile radius of select Walmart stores want something from the retail giant, they too can have it land safely in their yard.

As General Counsel of Wing, a leading residential drone service, Chadwick helped seal the deals with DoorDash and Walmart and is working on more. According to her, the sky’s literally the limit for Wing, though there remains a lot of work to create the legal and business principles that will shape the growth of Wing and the drone delivery industry.

She means business

“I came here with a mandate to build the business,” the ever-personable Chadwick tells Vanguard in May from Palo Alto. “Urgency becomes important as large retailers compete to see who can deliver most efficiently. That’s where we can be their partner.”

Chadwick’s skills for such an enterprise were honed by her 2018-to-2022 stretch as Associate General Counsel in charge of global compliance at Tesla, a role she was proud to have for a company whose mission she supports. Fulfilling as that role was, she aspired to be a general counsel and to help build a company from its infancy.  When she first heard of Wing, drone delivery was still in the research and development, and the industry’s future was unclear.

“When I joined the company, it was looking for leaders who understood business to business,” she says. “People who understood how to grow and scale.  I was hired to help guide  that B2B shift.”

Two years later, Chadwick has proven her chops as a business-savvy legal boss.  She has also enhanced Wing’s legal capabilities by hiring a talented staff of skilled lawyers, which includes experienced attorneys from Apple, Meta, and Google. Her team, she explains, comes from cutting-edge companies and—like her—is smart, hungry and eager to keep building.

And it’s been essential that the team perform. Each new agreement in this nascent industry is bespoke, and Chadwick and her team spend a lot of their time with issues of first impression. From the initial pilot agreement with Walmart to enhancing their partnership to now reach more than 60,000 homes in the Dallas-Forth Worth region, Chadwick’s experience has been essential.

So, how does Wing work?  Customers shop as they normally would with Walmart and Doordash apps,  enter their address to determine if they’re within delivery range, and if so, receive their order in as little as 15 minutes. Chadwick marvels how anything from frozen treats to hot coffee can be delivered without thawing or spillage through Wing’s engineering acumen.

“Don’t ask me how,” she says with a laugh. “I’ll just say that our engineers are the best.”

Chadwick goes on to say they’ll get even better. Wing’s current delivery load is just under 3 pounds, and its focus is on small products. However, Wing’s offer will likely expand, and when it does, she’ll mind the details. The company is also making its presence known in international markets, including Ireland and Australia.

Learning on the fly

On the home front, however, Wing’s delivery drones soar within the boundaries of  Federal Aviation Administration rulebooks. Drone delivery is relatively new for regulators. Most of the rules are set up for crewed aircraft carrying humans. So as Wing has scaled, it has had to get exemptions from rules that require commercial aircraft to have seatbelts and carry flight manuals onboard, neither of which is needed, or would even fit, on an 11-pound, uncrewed drone that does not carry humans.

But navigating through such gray areas is what she considers part of the fun of counseling a drone deliverer. Chadwick looks for the same mindset in those who round out her staff, even if they—like her—have much to learn.

“One of the questions I always ask candidates is “What have you learned through failure,”” Chadwick tells me. As she is building her team, she looks for those who have experienced moments of intensity and know what to expect as a result. “I need people who have a sense of urgency from their experience and understand the lessons from those challenges.”

Chadwick acknowledges lessons learned the hard way through a career that commenced as a commercial litigation associate at Troutman Sanders following her graduation from Harvard Law School. Entertainment law drew her in, and she got her foot in the door two years later with Katz, Smith & Cohen, an Atlanta firm whose clientele included such celebrities as Willie Nelson, Bobby Brown, Jimmy Buffett and Toni Braxton. That prepared her for her dream job in 1996 at Motown Records in New York.  She was there for almost four years when she got a cold slap of reality.

The music business was changing, and the record industry was soon to battle a number of innovative newcomers who had found ways to share music via the Internet. While the old-school music industry had strong claims for copyright infringement, there was no stopping the transition to digital downloads. Lesson learned.

“If you see a sea change coming, you might want to fight it, but you can’t stop progress,” she says. “Neither should you want to. The record industry imploded, and that’s why I left Motown. I cried because I loved that job so much. I had performed well, but I was still laid off.”

The career she wanted

But, as she reminds herself, going down doesn’t mean staying down. She picked herself up and grew professionally and personally with roles at Verizon (2000-2003), Atlanta Housing (2003-2016), a judgeship at Fulton County Magistrate Court (2016-2018), and Tesla before joining Wing. The Atlanta Housing position will always be among her career highlights. Chadwick plays a key role in transitioning from traditional public housing—“concentrated areas of poverty”—to more amenity-rich, healthier, more modern housing choices in mixed-income, mixed-financed communities.

“A transformative experience for me,” she recalls. “We had to be super creative and stand firmly on the position we’d taken. Many in the media didn’t like it, certain politicians didn’t like it, and we got heat from many. However, we also had major support from many stakeholders, so we worked with private developers to build a new model for increasing affordable housing choices.  That model has been replicated nationwide as a proven, new, improved model that works.”

She factored in building a new model of a different type at Tesla, the Texas-based pioneer of electric battery-powered cars and other energy-saving devices such as solar panels. While Chadwick says she was proud to play a role in that company’s growth, she feels she can do more leading Wing’s legal and compliance functions.

“If it’s major transformation or growth a company aims for,” she says. “I’m built for it. It keeps me up at night but in a good way. I’m constantly jotting down notes on my phone for ways we can do more and do it better.”

And her inspiration?

Well, one of them was Phylicia Rashad, who played the lawyer wife of a doctor husband in the 1980s’ “The Cosby Show.”

The epitome of what I wanted to be,” Chadwick says.

Chadwick’s more authentic role models were her parents, who taught and inspired their daughter to pursue education, which she did as a University of North Carolina business student who earned an MBA at The Wharton School and a law degree at Harvard. Her husband, Ken Grimes, a managing director with Bessemer Trust wealth management firm, has been an important part of her full journey, having been her prom date at the North Carolina School of Science and Math and her partner for many years since.

While her team works on expanding drone delivery to neighborhoods everywhere, life’s good in California’s Bay Area, where Chadwick fulfills her cultural itch by frequenting live music venues and salsa dancing. She also finds time to teach a business communications class at The Wharton School and, amongst the other lessons, emphasize the message her parents communicated to her while growing up in North Carolina.

“Education helps to equalize the playing field,” she says.