You might not have noticed Gina Tirado Strayer Ma on her first day of school at Hillbrook. She was a three-year-old preschooler, and she was hiding in her cubby. But because of patient and gentle teachers, she soon engaged fully with life at Hillbrook throughout her elementary and middle school years, graduating in 1997 and winning the 8th grade English award.
Today, Gina is known for her work at the ride-share company Lyft, where she was employee number one. Called a “female visionary” by Marie Claire magazine, she built out Lyft’s original driver community, and personally trained their first 500+ drivers, living in multiple states to launch new markets, before serving as brand manager and, most recently, Head of Driver Experience. In her life and career, Gina has lived by the “Do Your Best” motto of her time at Hillbrook, and followed her heart to take risks that have enabled her to make a difference in the world.
As a Hillbrook student, Gina found an environment that nurtured her as a learner and as a person. She loved Spanish with Ms. Martin, where she gobbled up the vocabulary and language of the Puerto Rican side of heritage. “Growing up half Puerto Rican in Los Gatos was an isolating experience culturally, because the only other people I knew like me were my cousins,” she says. “Ms. Martin’s classroom was a place where I could learn more about the language of my family heritage, and I took it very seriously, intently listening to Ms. Martin’s accent, and soaking up every single vocabulary word I could get my hands on.” Gina also thrived in the arts programs at Hillbrook, working with wood or throwing pots in Ms. Aikman’s creek-side studio classroom. “It was this sacred space that felt sanctioned from the rest of the world, a place where time slowed down and I could get lost in a state of flow and joy,” Gina says.
From a very young age, Gina’s greatest passion was writing. She recalls, “I remember the excitement of getting to bind my own books in Ms. Finkas’s first grade class, and how much I loved to write and illustrate stories.” This penchant for writing continued during her time at Los Gatos High School, where she became editor-in-chief of the school paper, and in college at the Medill School of Journalism at Northwestern University. “I fell in love with the power of journalism to shed light on important teen social issues like drunk driving and eating disorders, and I found myself drawn to telling human stories that changed how people saw the world,” she says.
In keeping with Hillbrook’s mission to help students reach beyond themselves to make a difference in the world, Gina’s early career focused on encouraging change for underserved people, with projects as varied as volunteering at a Latina advocacy group in Chicago, traveling on a research grant to do a senior thesis on the HIV/AIDS epidemic in Puerto Rico, working at a nonprofit in Washington D.C. that was bringing internet access to low-income housing across the country, and joining an editorial team that was creating bilingual content around financial literacy, health and other topics.
At that time, journalism was changing, and Gina recreated her skills for the digital age. She also recognized that she could equip herself to make an even greater difference in the world by expanding her business skills, earning an MBA from UC Berkeley’s Haas School of Business. While Gina’s career appears meteoric in its outlines, she has had hard knocks as well, earning her Silicon Valley badge of honor when the start-up she worked for post-MBA went belly up.
Hillbrook celebrates taking risks by equipping students through practice in a supportive community. Taking a job at Lyft was a huge risk for Gina. “Of course, I was nervous to start something so new, in the field of transportation, which I knew nothing about,” she says. “But I made an instinctive, heart-led decision to join this company, because I trusted the people I was working with. That human connection is what fueled me and made me feel supported.” Human connection also drew her to Lyft’s mission, which is “rooted in bringing people together to build a better world — providing economic opportunity for drivers, providing safe rides for passengers, and people making an authentic connection along the way. “
When Gina returns to Hillbrook now, every space holds memories, from the art building to the oak trees, and especially crossing the bridge onto the middle school side of campus. “Walking from the middle school to the gym was also filled with memories,” Gina says, “reminding me of the excitement of going to play rehearsals, the nervousness before playing a basketball game, and the everyday camaraderie of being a cool upper schooler inhabiting that side of campus.” Gina is currently enjoying life as a full-time mom to her one-year-old daughter, creating the space to consider what her next adventure will be.
Through it all, she follows the advice she offers to current Hillbrook students. “My advice is to lead with your heart,” she says. “My best decisions have come from knowing what feeds me, and jumping wholeheartedly into what I feel passionate about. You don’t have to have a perfect five-year plan; to me, the most important thing is being aligned with what gives you energy and meaning.”
