This story is part of our March 2025 issue. To subscribe, click here.

Cassandra Jennings

President and CEO, St. HOPE

All through school, Cassandra Jennings was a straight-A student. So when she got her first-ever B — in a college bowling class, of all things — she went to the instructor and argued (unsuccessfully) for a higher grade. More than 40 years later, she says with a laugh, “I’m still mad about it.” Now president and CEO of Sacramento’s St. HOPE, Jennings still has the attitude of the straight-A student she once was. “I’m a get-it-done sort of person,” she says. “I do what I do with a lot of passion, nonapologetically.”

At St. HOPE, Jennings oversees a collection of nonprofit entities — including a charter high school, a development company and an endowment — aimed at revitalizing the Oak Park neighborhood. It’s the culmination of her decades-long career in leadership roles at the Greater Sacramento Urban League, Sacramento City Hall and SHRA, the city’s housing and redevelopment agency. She is, and has always been, a community builder.

The seeds of Jennings’ future work were planted in her childhood. She was born in the segregated South, and when she was in fourth grade, her parents — both educators — moved the family up north to Maryland for more and better opportunities. There, she recalls watching white residents move out as Black ones moved in. Even as a child, she couldn’t help but see inequities in the way people were treated based on where they lived, the color of their skin or how much money they had.

After graduating from the University of Maryland with a degree in urban studies, she married her college sweetheart, Rick Jennings, and followed him to Oakland, where he played professional football for the Oakland Raiders and was on the 1977 Super Bowl-winning team. Meanwhile, she worked for the city of Oakland, helping first-time homeowners. There, they bought their own first home and had two kids. By 1986, when the family came to Sacramento, their Oakland house, purchased in 1979, had appreciated greatly, enabling them to move up to a bigger, better house. For Jennings, it illuminated in stark and personal terms the importance of homeownership.

“I’m a get-it-done sort of person. I do what I do with a lot of passion, nonapologetically.”

After stints as assistant city manager, senior adviser to Mayor Kevin Johnson and CEO of the Greater Sacramento Urban League, she went to St. HOPE in 2021, where she now comes up with ways to enrich and engage the Oak Park community. It might be an author’s talk at Underground Books, a Black business expo or a Juneteenth block party. Books and the arts are key: There’s a film festival and a speakers series at The Guild Theater, and St. HOPE recently took a group of students to see the August Wilson play “Fences.” Jennings sees St. HOPE as an equalizer that can provide students with the extras that middle- and upper-middle-class families give their kids as a matter of course. Ninety-five percent of St. HOPE graduates are eligible for admission to UC Berkeley, she points out, “but they are still Black or marginalized and don’t have access to all the things that people who go to Berkeley have. We are their extended community — their village.”

St. HOPE also helps businesses get established in Oak Park, so they can act as “catalytics” to further development. The organization recently bought land for housing next to McClatchy Park and is renovating a dilapidated elementary school in South Oak Park because, as Jennings says, “you can’t expect academic success in a rundown facility.” 

Dressed in her signature pearls, which she wears with everything from football jerseys to business suits, Jennings cuts a highly recognizable figure in Oak Park. At 68, she could retire to spend more time with her husband (now a city councilmember in his third term), their two adult children and six grandchildren. But, as she says, echoing a lesson from Lin-Manuel Miranda’s “Hamilton,” “You gotta be in the room where it happens.”  

View the list of honorees from 2015 through 2025.

Get all the stories in our annual salute to women in leadership delivered to your inbox: Subscribe to the Comstock’s newsletter today.