BUILDING LIKE A BOSS. Sophy Lee is the chief technology officer at HopSkipDrive, a platform that provides transportation solutions for children and the elderly. Despite her credentials, being recognized as a leader can still prove challenging. During many conversations, she recalls, vendors ignored her so blatantly that male coworkers steered them back to the boss: Sophy. “It’s comical at times,” she says, “but it can be an asset when others underestimate your capability.”
Recognizing one’s own capability is vital, Sophy says, because the steadfast belief that one can solve a task actualizes that reality. And that belief arose early in her childhood. “I’ve always been dissatisfied with the way things work out of the box. I felt things could be better, faster, and cost less money.”
“I’ve always been fascinated by what it’s like to perform at the edges of human potential,” Sophy says. She doesn’t emulate a specific person but is guided by an objective benchmark: being qualified. “You know you’re qualified when you win the thing,” she notes. Some of that drive came from her upbringing. “My mom was very demanding. If I went to a competition and got second, she asked, ‘Why didn’t you get first?’” That ignited Sophy’s drive to be the best.
Being the best doesn’t mean doing everything alone. After her company Shuddle was acquired by HopSkipDrive, Sophy took on a daunting data migration project and completed it in three months... by herself. “I played the role of the lone wolf. I wanted to prove that I was good enough to figure it out by myself. I thought asking for help would mean I was too weak to solve the problem.... I would tell my past self to stop trying to do things alone and not to hesitate to reach out for support. I might be surprised how many people are willing to help.”
THE NOTION OF "WOMAN" AS A ROLE MODEL. Sophy spent years hiding her identity from colleagues. “I tried to hide parts of my identity and not accentuate them because I was afraid they would detract from my credibility.” She worried people would not take her seriously if they knew she was a woman. Some coworkers thought she was in her 30’s, and she worried her contributions would be dismissed if they knew she was really in her 20’s.
Sophy had internalized her parents’ narrative that it’s a man’s world, and gay people can’t be successful. “My mom told me I was destroying my career by coming out,” she recalls. As a young adult, that message hit hard, especially since there were no role models to shape a different worldview. Most successful engineers were cisgender, white men, she notes. And a part of her wanted to belong in that world.
Today, she mentors with the global community Lesbians Who Tech, sharing her story at various summits. “Each time I’ve attended and contributed to a summit, I’ve always made an important professional connection.”
After years of being told what was not possible, Sophy now knows the truest messages come from within. “I was so good at reading my environment and matching the pace of people around me to be successful, but I’m now learning the importance of balancing that with being authentic to myself,” Sophy notes. Being a chameleon was tiring, and illuminated a certain emptiness, she explains. “I’ve learned to walk away from situations where I don’t feel like my true self.”
