Shearman & Sterling Alumni Spotlight

Through the Alumni Spotlight series, you can meet a few of our distinguished alumni to learn how they leveraged their time at the firm to advance their careers and what advice they would give to those looking to have similar success.

Ann Mao General Counsel Headlands Research

Ann Mao ’06 (Mergers & Acquisitions, 1996–2008, New York City/San Francisco) moved to the US from South Korea when she was four years old. She studied chemistry at Wellesley College in Massachusetts before realizing it wasn’t for her. She subsequently attended Fordham University School of Law in New York and worked as a summer associate at Shearman & Sterling, where she remained for 12 years before leaving to work for pharmaceuticals, health IT and medical supplies company McKesson. Ann is now General Counsel at Headlands Research, an international network of clinical trial sites that focus on diversity, quality and cutting-edge technology.

What is your favorite memory or story from your time at Shearman & Sterling?

One of the most career-defining was when we were representing GE in the spring of ‘97. A partner had been pitching GE for a long time, so we were excited but understood that we had to perform at a high level. We met in Florida for a week of intense diligence and deal negotiations. We were working long, hard days, but also laughing and having fun.

But I’ll never forget getting back to the office and a senior associate had put an article from the New York Voyeur, or some other rag, on all our desks. It was an interview with the special advisor to Jack Welch [former CEO of GE], who was quoted as saying, “I don’t see the point in spending money on first-year associates. They’re just a waste.”

When we had an in-person meeting with the special advisor a week later, she sat us down and said, “I know you all saw that article, but I don’t mean that about this team. You did a great job.” Fun memories!

What skills or capabilities did you gain from your time at the firm that prepared you for future roles?

If you do the work, Shearman provides great training, but you need to lean in and be willing to learn. I also learned to listen to the client to try and help them achieve their goals. It’s easy to say, “No, that doesn’t work,” or “No, that’s too risky,” as a lawyer. But a good lawyer listens and says, “Tell me what your goals are and let’s try and get there.” It’s about trying to balance goal achievement and risk.

That’s also the way I negotiate agreements or deal terms. Tell me what’s important to you, I’ll tell you what’s important to me, and let’s try to find some ground in the middle. Sometimes, especially when dealing with New York lawyers—less so now, but when I first started—it’s a zero-sum game. I’m just going to beat you up until I get what I want, whether or not my client needs or cares about it. It’s probably partly my personality, but I always tell people, especially in M&A, that you need to work with these people and actually make a deal. If you’re so antagonistic, it can rub off on the principals, and that’s no good for anyone.

What has been your career journey since leaving Shearman & Sterling?

I left Shearman after I had my second child. My husband is a partner in a law firm on the West Coast, so it just wasn’t going to be tenable. I went in-house to McKesson—one of the oldest healthcare companies in the country—which back then was based in San Francisco. I ran their M&A legal function for about four years before becoming Senior Vice President.

I left after we merged McKesson’s healthcare technology business with Change Healthcare in 2017. I probably worked more hours over the year and a half it took to get that deal done than I ever have, even at Shearman. After that, I took 18 months off. I needed a break, and it was the right time for my family.

In February 2019, I joined Cargomatic, a small private logistics company, as General Counsel. I enjoyed three years there when the opportunity for General Counsel at Headlands Research came up. I realized how passionate I am about working in healthcare and doing something I find personally impactful.

Tell us about your current job. What do you enjoy most about your work?

I am the sole lawyer at my company, so I get involved in all legal issues–big and small–that come up. I really enjoy the diversity of the issues that I am asked to opine on. In a company our size, I also get involved in more of the “business” side of things and learning what drives the profitability of this business and how it operates has always interested me. Lastly, I really enjoy the people that I work with. I would count many of them as friends and not just work colleagues. I feel like I was lucky to have that experience in all my jobs (starting with Shearman & Sterling), and that has made my career much more rewarding.

What advice would you give to someone looking to have a similar career path?

Do the work. I tell my kids this all the time. Malcolm Gladwell talks about how it takes 10,000 hours to become an expert at something. We could argue it’s not 10,000, but 9,000 or 8,000, and it’s getting shorter because of the internet and Artificial Intelligence (AI), but AI can only do so much. It’s important for a lawyer to read a lot of documents and understand how to do things the right way. It’s also good to talk to people, as you never know where the next opportunity will come from.

Think long and hard about getting to a certain level at a law firm before you make a career jump. Many leave before they’ve really gotten the benefit of the training, but having that expertise and background gives you a lot of flex. It gave me flex to take a year and half off. I’d worked hard and gained experience over almost 20 years, so I knew I could get back in if I wanted. You don’t necessarily get that if you leave a law firm as a second-year associate.

Finally, focus on the people when choosing a place to work. Are they the type of people you respect and want to spend your time with? It’s important that your personality, the way you communicate and your ethics are reflected in those around you.