Alumnae News SPRING ’25

The Power of a Pivot

Navigating career transitions can be daunting, but a recent alum webinar demonstrated that embracing change—both anticipated and unexpected—can lead to rewarding opportunities. Hosted by Danielle Johns ’05, analytical lead at Google, the webinar brought together an accomplished panel of Winsor alumnae to discuss career pivots

and the evolving nature of professional growth.

The panel featured Siobhán A. O’Riordan ’83, certified Gallup Clifton strengths coach and consultant and author of the upcoming book The Generalist Advantage; Maia Monteagudo ’06, one of Winsor’s school counselors and adjunct faculty at Lesley University; Emma Russell ’89, print sustainability and compliance lead at Canva; and Sarah Marlenga Powers ’05, senior manager at Bain and Company. Each panelist shared her career journey, illustrating the ways in which their paths have diverged from their initial expectations.

Opening the discussion with an icebreaker, Danielle asked each panelist to choose one word that best described her career experience. Their responses—bold, unconventional, curious, growing, and self-trust—set the stage for a rich conversation about the challenges and rewards of pivoting professionally. Panelists reflected on their early career expectations and how their views evolved as they gained experience.

Siobhán noted the importance of embracing one’s strengths and values rather than feeling confined by a linear career trajectory. Emma spoke about the difficulties of being a woman in STEM, later transitioning into the fashion industry, then shifting to sustainability, emphasizing the importance of trusting oneself despite moments of imposter syndrome. Maia highlighted the importance of work-life balance, sharing insights from her work with students and young professionals. And Sarah, who has navigated multiple industries and even returned to a previous employer—a pivot known as a boomerang job—spoke about the necessity of adaptability.

The webinar underscored that career growth is rarely a straight path.Instead, it’s an evolving journey that can be shaped by curiosity, resilience, and a willingness to embrace change.

The session concluded with panel participants offering a few words of advice. Emma summed it up well, sharing, “If you are thinking about a career pivot, don’t let fear stop you. Don’t overthink it too much. ...Just trust that voice that says, ‘go for it.’ Just give it a shot.”

Welcoming Alumnae with Open Arms

“There are three things I really enjoy about being involved in the alumnae board,” says Johanna Mendillo ’96, chair of the board’s nominating committee. “I love the chance to hear about and experience present-day Winsor; the insight into plans for the future of Winsor; and the chance to meet and work with other alums whom I didn’t know from school.”

Johanna compares the Winsor community to a puzzle or a mosaic: “It’s amazing to see how your Winsor experience is just one small piece, one individual story,” she says. “By getting involved with other alumnae, you gain an appreciation for so many more of those puzzle pieces,

and you get to think about the faces and stories that will join the Winsor mosaic in the future.”

For more than 100 years, a group of dedicated Winsor alumnae—first known as the Graduate Club, and later the Winsor Alumnae Association—has worked to encourage alumnae to remain involved in activities related to the school. The Winsor Alumnae Board, consisting of volunteers elected by the association, seeks to be a resource to alumnae for networking, support, and friendship; to provide the school community with volunteer support; and to plan activities and opportunities for alumnae to connect and to engage in ongoing learning.

“I think it’s really special to have a board that’s completely run by alums,” says Alumnae Board President Ashley Marlenga Herbst ’01. “Winsor alums are a special group. They’re brilliant, smart, dynamic, and interested in so many things. The board tries to keep people connected and give them opportunities to grow—intellectually and educationally, yes, but also practically, in terms of navigating career and life transitions. We want people to form connections across decades and backgrounds, and we’re trying to be the glue that keeps the community together.”

Ashley was living in the Boston area when she became board president, but soon after that, a new job opportunity took her to Dallas, Texas, where she serves as managing director of JP Morgan’s private banking office. She sees the move—and her resulting geographical distance from Winsor—as a strength in her role as board chair. “I’m uniquely positioned to help the board think about engaging alums nationwide,” she says. “For a long time, I had the joy of being local and getting to attend Winsor events on campus. Now I’m not in Boston, and I still want to be included and participate. It’s pushed me to think more creatively about how we can engage our regional membership in a different way.”

The COVID-19 pandemic, too, prompted the board to reimagine its events and other offerings to alumnae. Some graduating classes began holding regular Zoom meetings to check in on each other, some of which are still happening years later. Other events, such as virtual museum tours and book discussions, have drawn alumnae from different decades and backgrounds, who live in varied locations but have been thrilled to meet (or re-meet) fellow alumnae online. “COVID really opened our eyes to the art of the possible,” Ashley says. “It helped us imagine different ways to bring the Winsor community together.”

Reflecting on her past six years on the board, Mary Noonan Quirk ’05 shares, “The board has evolved in two distinct ways. First, there is greater global outreach to alumnae across all states and abroad. Second, the events organized by the board seem increasingly self-driven. There has been a focused attempt to generate more active involvement from alums, rather than passively attending something organized for them.”

“We’re full of ideas for alumnae events!” says Jennie Skeele ’71 P’98, ’02, a long-time English faculty (now retired) who helped develop a poetry discussion featuring retired colleagues Judy Robbins and Tyler Knowles, and who herself hosted an online discussion of Jane Austen’s Pride and Prejudice. “We want to draw people back in, and learn about what they’re doing now. Winsor alumnae are dynamic and interesting—that was true when they were teenagers, and it’s true of them today. I’m amazed by the amount of energy and commitment from people who are doing all kinds of things all over the country, who are getting involved because they want to be emissaries for this school.”

Having served the school as a teacher and a parent after spending her own formative years at Winsor, Jennie has been astonished by how much there is to learn after joining the alumnae board. “I thought I knew a lot about Winsor, and I do!” she says. “But I didn’t really know how the board worked. We have several committees, and I’m on the Education Committee, which works to put together events focused on learning. Our alums have so many gifts and talents to offer.”

“You don’t have to be on the alumnae board to serve on a committee,” adds Ashley. “For people who want to give it a try, joining a committee can be a great first step.” The board’s current committees are focused on areas such as education, community engagement, career and personal development, regional events, and special projects. The nominating committee, chaired by Johanna Mendillo, works to recruit a diverse group of alumnae voices to serve on the board each year.

Jennie also notes the board’s ongoing role as a bridge between Winsor’s alumnae, who carry their own experiences of the school’s past, and its constantly evolving present and future. “Schools are constantly growing. They’re always changing,” she says. “The Winsor our alums remember, in some cases, is not the Winsor we have now. The overarching trend in education is more inclusive, more diverse, more interested in a student’s entire range of gifts and talents. We now have systems that support students’ mental and emotional health in ways we didn’t—at least not formally—when I was a student and even a teacher here. And we have a much more diverse student body now, in many ways. There’s so many different kinds of excellence and interests and talent. It’s an exciting time to be at Winsor.”

Staying connected with other alumnae—not only from her own class, but from many others—has been a delight for Katherine McCord ’02, client communications and reporting vice president at HarbourVest Partners in Boston. “I truly have Winsor friends now who span decades,” says Katherine, who is also co-chair of alumnae annual giving at Winsor. “Being part of the board has helped me connect with alums from different years—and decades!—whom I now consider good friends.”

Katherine adds that the board’s events, from Alumnae Weekend to virtual museum tours, are planned to appeal to the Winsor community’s broad range of interests. “We have such a variety of talents and expertise,” she says. “Coming to events, on campus or online, is a great way to meet new people, and perhaps find a mentor in your field, or look for advice. You have this immediate bond and connection as Winsor alums, and the community can provide valuable professional support.”

“The relationships I’ve built have been amazing,” Ashley agrees. “The board is an incredibly engaging group of people with high energy. It’s a small way to ensure the legacy of the school going forward, and to stay in touch with our community, meeting them where they are.”

Katherine’s final advice is for current Winsor students: “When you graduate,” she says, “you’ll be welcomed into this community of brilliant, driven, motivated, smart, successful, spectacular people who are there for you to connect and be friends with. We can’t wait for you to be a part of the alumnae community.” As Mary Noonan Quirk puts it, “It is never too late to join. There are seasons to our lives, some busier than others, but I trust and have seen that Winsor will always welcome its alumnae with open arms.”

To learn more about the Winsor Alumnae Board, visit www.winsor.edu/alumnae.