JUST LIKE US

A new local player is bringing fresh energy to user-focused product design and development.

Sydney Caine, a longtime North Shore resident, is charting her course with purpose and presence. A senior leader at Google working at the intersection of tech and healthcare, a mother of three boys, and a dedicated nonprofit board member, Caine fiercely believes in staying grounded, being present, and lifting those around her.

“I don’t have a traditional tech background,” Caine says with a laugh. “I was in brand management and advertising. I thought I’d stay in CPG (consumer packaged goods) forever.” Eleven years ago, Caine, who had formerly worked at OMD and Draftfcb and whose accounts had included McDonald’s, Bayer, Boeing, and Sharpie, was a Brand Manager at Kraft Foods. Caine was deeply involved in projects focused on developing new product offerings and managing creative marketing campaigns for the JELL-O brand when Google reached out to her about a role. She spoke with Karen Sauder, a fellow North Shore resident and senior executive at Google whom Caine had worked with previously, and Sauder provided the insightful advice Caine needed to confidently take on this new business challenge, propelling her to make the significant leap from packaged goods to big tech.

That early encouragement stuck with Caine. “Karen believed in me, and now I try to do the same for others,” she says. “I’m building and mentoring teams at Google, and I hire people I believe in. Maintaining a strong network has been key at every step of my career.”

Caine leads Google’s partnerships with major healthcare brands, where her most important role is to work with customers with a mission to improve patient care, reduce costs, and make healthcare more accessible to everyone. “I entered this space right before the pandemic. Suddenly, these companies had to shift their entire messaging, from acquiring new members to educating the public on how to get vaccinated,” she explains. “It became about using Google’s platform for real public service.”

This is where Caine’s passion lies—using marketing not just to sell, but to help. “I work with people who care deeply about improving lives, whether they’re chief medical officers or brand directors,” she observes. “They’re tackling huge challenges in a complicated system, and I get to help them tell important stories in a meaningful way.”

That sense of purpose fuels long days filled with meetings, strategy sessions, and mentoring her team. Google’s hybrid model allows her to work from home on Mondays and Fridays, precious time she uses to walk her sons to school and grab coffee from the local Starbucks. Tuesdays through Thursdays, she heads into the city, catching the train after waking the kids and squeezing in her daily workout. “Fitness is nonnegotiable for me. It’s how I create some ‘me’ time and clear my head,” Caine notes.

As for how she juggles it all, Caine relies on structure and help. She and her husband, Adam Freeman, recently welcomed their second au pair, this one from Germany, to assist with mornings and after-school chaos. “I don’t need full-time childcare anymore, but I do need full-time support,” she says. “And I love that my boys get to learn about different cultures right in our home.”

In the margins of her already full life, Caine finds time for board work. She serves on the board of the Anne Frank Center USA and on the Executive Committee for the Children’s Service Board at Ann & Robert H. Lurie Children’s Hospital of Chicago. “That work keeps me grounded. It reminds me of the power of empathy, of standing up for others,” she explains. When asked how her nonprofit work has shaped her leadership and parenting, she doesn’t hesitate. “It’s about the power of educating young people to become great changemakers. I try to carry that forward, whether I’m at the office or at home.”

Her advice to others is simple but powerful. “Get involved with a board that’s close to your heart,” she urges. “Find something that aligns with your strengths and participate in a way that makes a real impact.” For her, there’s a personal connection to Lurie’s Children’s Service Board. “The amazing doctors and nurses at Lurie’s cared for my kids when they needed it most,” Caine reflects, her voice filled with emotion. “I’m incredibly grateful—and proud—to give back and support the mission.”

Speaking of community, Caine and her family can often be spotted around the North Shore, visiting friends and family nearby, attending school events, taking fitness classes at CorePower Yoga, or grabbing treats at Hometown. Another passion is watching her sons’ sports games. “I love being on the sidelines, cheering on my kids and catching up with other parents.” For her, true success comes from creating meaningful connections. “It’s those moments that really fill me up.”

It is sometimes said, “The more you do, the more you can do.” Caine is living proof that leadership isn’t just about titles or accomplishing important tasks but about showing up for the things that matter. Caine is a vibrant model of living a balanced, purposeful life to the fullest.