Playing for keeps: The Grand Del Mar's 18-hole, 72-par, Tom Fazio-designed golf course boasts numerous features, including a trickling stream with a stunning 18-foot waterfall, a 4,200-square- foot putting green and scenic fairway views of the Los Peñasquitos Canyon Preserve.
Robert Dahey

Gillian Smith

Occupation: Chief Marketing Officer, City Year
Home base: Coral Gables, Fla.


American Way: You commute from Miami to Boston for your job with the nonprofit group City Year. Can you tell us more about this group?
Gillian Smith: City Year is an education-focused, nonprofit organization that partners with public schools and teachers to help keep students in school and on track to succeed. We’re in 24 cities across the United States, and we have teams of young people serving full time to provide individual support to students who need extra care and attention, focusing on attendance, behavior and course performance through in-class tutoring, mentoring and after-school programs.

AW: You’ve also had media/marketing positions with Coca-Cola and Burger King. How does working for a nonprofit differ from working for a big corporation?
GS: Ultimately, marketing is the same discipline whether it is for a nonprofit or a for-profit. The biggest difference is that I have to be more resourceful in nonprofit because we have fewer financial means to effectively target the people we are trying to reach. It is certainly more rewarding to be able to go home and know that each day I’m helping improve students’ lives — even if I no longer fly Business Class.

Getting to Know GILLIAN

Right now I’m reading: Some David Sedaris short stories and a travel guide about Iceland

I never leave home without: My running shoes

Worst job I’ve ever had: One summer during college I was a counselor (RA) at an overnight camp, and the teenage girls I was responsible for contracted lice.

Last thing I bought: Seriously — I bought three of the dresses I wore in the Road Warrior shoot. I think I now need a personal stylist.

Best meal I’ve had on the road: Years ago, I had some steamed berberechos (they are like little clams/cockle shells) in Spain. I still think about them a decade later and wonder where I could get some fresh ones.

Favorite hotel: I must say that The Grand Del Mar was pretty fantastic.

Last song I listened to: A mashup of Chubb Rock and Steely Dan called “Peg Me Right.” Mashups keep me moving when I’m out for a run.

Beach or mountains? We live near some spectacular beaches that we visit all the time, so we tend to vacation in the mountains.

AW: We heard that Grey’s Anatomy star Patrick Dempsey once got your phone number. What’s the story there?
GS: Several years ago in a previous for-profit role, he and I met at a media event, and he was looking for a sponsor for his race team. I was overseeing large media budgets at the time, and we had done some NASCAR sponsorships — so he wanted to chat with me. His wife’s name is Jillian (same pronunciation as mine), so he never forgot my name.

AW: Along with juggling a career with a commute, you have two sons. How are you training them to be Road Warriors?
GS: [My husband and I] got both of them AAdvantage memberships as infants, and they’ve already traveled to four continents. We knew in order to get them comfortable with long flights, it was critical for them to begin traveling at young ages. They’ve become excellent travelers. When they know that we’ll have a long flight ahead, they each pack their own backpacks with games, books and other forms of entertainment. (Now we have a tablet, thanks to Samsung.) We let them weigh in on where we are planning to take family vacations. Given their ages, sometimes there is something specific they’d like to see — like volcanos or penguins. My oldest son is 9 years old and has already logged more than 65,000 miles.

AW: Your 9-year-old son has 65,000 miles? Really? He might hit Executive Platinum before you do.
GS: My youngest son [7] even used the term Road Warrior in creating a personal user name for himself on a website a while back. They also get particularly excited when they get mail from American Airlines.

AW: What are you going to do with the 500,000 miles you’ve won?
GS: I’m donating all of my winning miles to City Year. I can think of a million places I’d like to go myself, but ultimately I know that the best use of them is to give some of the amazing young people we have serving in schools [the opportunity] to travel to other cities — and give them a chance to see another part of the country. It will mean a lot to them.

AW: How did you drum up support and votes during the online voting portion of the Road Warrior Contest?
GS: In addition to the typical social-media and friends–and–family outreach, I wasn’t averse to introducing myself to strangers on my trips (including TSA), and I even handed out some of my kids’ Halloween candy to fellow passengers in November (don’t worry, they had an impressive bounty and got a lot for themselves). I also created a video that we sent to the City Year corps members and staff, and once they all heard I was going to donate the miles, lots of people started voting for me and encouraged their friends to do so too.

AW: Speaking of TSA, I’m guessing that in traveling so much, you’ve developed quite a rapport with the flight attendants and TSA agents?
GS: The folks at [Boston] Logan, in particular, know me quite well. I even introduced some of the TSA staff to my kids when we went through pre-check together. [And] two weeks ago, one of the agents said to me, “We were just talking about you, wondering when we’d see you today!” Apparently, I’m one of their regulars on Fridays.