Jan Singer, a veteran consumer and retail executive at major global brands, will be the keynote speaker at Loomis Chaffee’s 110th Commencement on Sunday, May 24. As she looks out to the audience on that day, two faces will be especially familiar — her twins, daughter Sophie and son Max, members of the Class of 2026.  

Jan is a senior advisor for Google and on the Board of Directors of Acushnet Holdings and Brown-Forman. She has been the chief executive officer at J Crew, Victoria’s Secret, and Spanx; a corporate vice president of Nike; and a vice president of Reebok. Earlier in her career she had executive roles in communications and marketing in the luxury goods sector.  

Jan, whose brother is Edward Sharkansky ’86, grew up in Brockton, Mass., south of Boston, a city often referred to as the “City of Champions,” in large part because of its rich boxing history that includes undefeated heavyweight champion Rocky Marciano and Marin Hagler, the undisputed middleweight champion for nearly seven years. 

“I knew that while I was fourth-generation Brockton, there was a big world out there, and it was going to be my mission to get there,” Jan said. “I was going to get outside Brockton, which was a great place to grow up, and make a difference.” 

She said she was an average student in a high school graduating class of 1,500 and an average student at Ithaca College, where she earned a degree in psychology and business. “I realized a couple of things along the way, starting with my dad and those who influenced me,” Jan said. “You have to get the easy things right. Ace the easy things. Be on time. Be present. Be organized.” 

From there came other advice. “My dad would always tell me it takes people helping people, so I always made time for people, and they always made time for me,” she said. “Through that, I found my way to many incredible moments. It also took being willing to do whatever it takes, without complaining, with accountability and integrity.” 

Her first job was as a secretary. “I took a job anywhere I could in New York City just to get to New York City,” she said. “And I went from secretary to CEO under all the lessons I learned, not because I was No. 1 in my class, but I was willing to get the easy stuff right, do what it takes.” 

She may have left Brockton, but you cannot take Brockton out of her. “What I got from Brockton was work hard, value family, and want to win,” she said. She certainly has been a champion in her line of work. 

Consumer preferences change — and she has had to stay nimble and change with them — but there always has been a constant approach, a service mindset. “You’re there to leave things better, and I look at how can I make this person, this moment, this business better, easier, and more efficient,” she said. 

Fatherly wisdom informs her service mindset. “My dad would always tell me to find my own problems to solve and not wait for people to tell me what to do,” she said. ”So I think about what [does] the consumer need, what [does] the employee need, what does my boss need, what does the stockholder need, what does the board need? I’m always thinking that way. I think about it with my family.” 

Her service roots were heavily influenced by her parents’ professions. “My dad was an accountant, which is a service business, my mom was an IC [intensive care] nurse for 54 years, so I was raised that way,” Jan said. “It doesn’t matter what level I was at, what company I was at, what city I was in ... there was somebody who needed something so that is how I think about my work in general.” 

Another reason for her success, she said, is that she always looks to innovate. “It doesn’t mean turn stuff on its head,” she said. “Just constant improvement. Don’t be satisfied with the status quo. Things can always be better, different. If you think of things outside the box, out of a routine, you can find a problem that needs to be solved, and generally it is an improvement. Sometimes it might not work, but you learn from that, and you move forward. Always forward motion with me.” 

And it doesn’t hurt that she might see something others missed when consumer preferences start to shift. 

“People ask you, ‘What’s your superpower?’” she said. “Everyone has a superpower on some level. I’ve always been able to see around corners, and I’ll tell you, I’m really nosy, a curious person, very curious about human behavior. Why do people do what they do, what makes them motivated? Why, why, why, why? And when you have that kind of curiosity and string patterns together, you can see ahead, predict where things might go. If you see a pattern and get ahead of it, you can drive the rest of the story. The consumer will come with you because they are on their way anyway. Patterns add up. Once is interesting, two is you better pay attention, and the third is a trend. I try to catch it at one or two, so I can push to the third.” 

Jan’s husband, David, is a retired Coast Guard search and rescue commander, yet another example of service to others. “He keeps us all on track,” she said. “I am proud of the kids and grateful for my husband. The only reason I can do what I do is David is the CEO here [at home]. He keeps us roiling.”  

Jan calls herself a dedicated golfer, “though it tortures me at times.” 

“Some of the best times Max and I have together are playing golf,” she said. The bond with Sophie, who has appeared on stage multiple times at Loomis, comes from their shared love of Broadway musicals. “We spend a lot of time talking about, listening to, and singing those songs,” she said. 

When Jan found out she would give the Commencement address, she called the kids by Zoom so that she could see their faces. They all left that call excited. Jan has a bunch of other feelings, too, one being how thankful she is for what Loomis Chaffee has done for her children in and out of the classroom. “It is not lost on me how many people there watch out for the kids,” she said. “I am grateful.”