Big Sister Boston CEO Deb Re retiring after 16 years

BOSTON - Big Sister Boston President & CEO Deb Re never had a sister. The youngest child in a family of five brothers, she says she was drawn to Big Sister Boston. "I know how important it is to have a mentor," she explained to WBZ's Lisa Hughes just hours after announcing her retirement.

Re says it's time to welcome a new leader to the organization. But the transition will be bittersweet. She still feels the same passion and enthusiasm for the group and its mission that she did when she walked through the doors 16 years ago. "This organization is focused on girls of Greater Boston. It's all about mentoring and it's focused 100% on girls," Re said. "It is such an honor to be in this position."

Through economic downturns, the rise in social media, a pandemic and a racial reckoning, Re says Big Sister Boston has been a steady presence for girls who often internalize their feelings. In times of upheaval and uncertainty, the consistent care of a Big Sister is reassuring. "So many adults in these girls lives come and go-no continuity and no consistency," Re explained. "But with a Big Sister, there is.... We are for just a year even though the relationships usually last much longer."

When the BSB staff matches Big and Little sisters, there is an understanding that-for the first few months-the two will meet once a week to establish a foundation. Over time, the relationship can grow into a friendship based on shared experiences and trust. That's how Victoria Kwong, now an admissions counselor at Simmons University, describes her experience with her Big Sister Jessica Reardon. She and Jessica were matched in the same year Deb Re joined Big Sister. "We clicked right away. It's a testimony to how intentional the matching process is," Victoria said.

She remembers, as an eight-year-old, participating in arts and crafts activities and joining Big Sister Boston events. Victoria's older sister had Big Sister and Victoria wanted one too-mainly for companionship. Over time, she says, Jessica became her confidante and ally. "We had conversations about finding my voice in spaces that I didn't feel comfortable in-maybe addressing that imposter syndrome-and going after opportunities that I thought I wasn't meant for... She has played a huge role in my academic trajectory and what I chose to study, the career path I chose-education," Victoria said. "My goal is to bridge opportunity gaps for underrepresented communities because I grew up in those spaces and I want to make a difference."

Years ago, Jessica took Victoria to the Little Sister's first Broadway show. (They saw "Wicked" which Victoria says she loved.) Now, because Jessica lives in Philadelphia, they meet in New York to go to the theater. When they learned that Re is retiring, both Victoria and Jessica (over FaceTime) remembered their experiences with the outgoing leader fondly. "She really set the tone for an organization that values personal relationships and creating opportunities," Victoria said smiling.

Under Re's leadership, Big Sister Boston has launched myriad mentoring programs-in schools, in workplaces and for girls planning for college. The organization's budget has doubled. And after two years without in-person events, Deb isn't resting on her retirement announcement. She and her staff are planning the Role Model Fashion Show featuring several Big and Little Sisters (Thursday, May 12th) at the Fairmont Copley Plaza. It will be a night to celebrate and reflect.

Re plans to depart no earlier than September. It will be a big change after 16 years. But she has no doubt that her successor will share her commitment. "What hasn't changed in this organization is our commitment to girls and our focus on mentoring; understanding that one-on-one relationships can have a transformative effect," Re said.