This story is part of “Ceiling Smashers,” a series in which successful women across industries tell Moneyish how they broke down professional barriers.

Jenifer Rajkumar knows what it’s like to be underestimated, both as a mid-20s lawyer staring down older male partners on a gender discrimination case and as a young City Council candidate door-knocking for votes. But there’s a silver lining, she told Moneyish: “People don’t see you coming.”

Rajkumar, 35, traces her lawyerly roots back to childhood, when disputes were resolved through a “family court system”: “One person would be a lawyer for one side, one person would be a lawyer for the other side, one person would be a judge, and we’d argue it out as a family,” she said. She went on to study at Stanford Law School, work on the class-action Velez v. Novartis and serve as a fellow at the National Women’s Law Center. During her foray into politics, she said, she became the first first-generation South Asian to serve as district leader of Manhattan’s 65th assembly district. In 2013, she mounted an unsuccessful bid to unseat incumbent Councilwoman Margaret Chin.

“Say you’re campaigning for votes on a street corner or knocking on someone’s door … When they first see you, they may be taken aback because you’re not the image of what they think a politician is,” Rajkumar said. “But what I found is that people come around. Because they’re persuaded by ideas and a person with convictions.”

Courtesy Jenifer Rajkumar

Gov. Cuomo last year named Rajkumar his director of immigration affairs and special counsel. She went on to serve in his executive chamber in August, acting as a statewide surrogate for the governor on his signature policy items, before returning to her original role this past week. (“We shift around a lot in government,” she explained.) As of August 2018, per a Cuomo spokesperson, Rajkumar worked in the Department of State.

Her career’s various chapters have been an attempt to “experiment with different levers of change,” she said: “That’s why I tried being a litigator to help workers; to help women. I tried policy at the National Women’s Law Center. I tried running for office. Now I work for the governor.” One of Albany’s draws, she says, was her boss’s penchant for “elevating women — not just in his policies by elevating working-class women and young women on college campuses, but also by (elevating) women into leadership roles.”

Rajkumar, the daughter of Indian immigrants, says she’s still trying to break her glass ceiling — or, as she sees it, “be in a place where I can empower the most people most effectively.” Hence her multi-pronged approach: “I think that it’s very important to block out naysayers and to try many different ways of making a difference,” she said. “It’s important to try something, and if it doesn’t work, get up fast and try something else.”

This story was originally published March 15, 2018, and has been updated.