Libby Schaaf’s career—first as an attorney, then running a nonprofit, and now as mayor of Oakland—is the journey of a cross-sector leader.
Oakland, Calif., Mayor Libby Schaaf’s career wound its way through multiple sectors, starting when she was an attorney at the city’s largest law firm, always seeking a way to make an impact. While Schaaf worked as a litigator, she and her mother launched Oakland Cares, a volunteer program providing busy professionals with one-shot volunteer opportunities.
Then, during one of Schaaf’s own volunteer experiences with Oakland Cares—tutoring children at a local school—she hit a tipping point. When Nathan, a 9-year-old boy she was tutoring, ran across the gym to greet her with a hug, she recognized that her real joy was in public service. Schaaf decided to leave the law firm to start a centralized volunteer program for the Oakland Unified School District.
When searching for her next position, Schaaf received a dream job offer to be a nonprofit program officer. At the same time, in the course of speaking to her network about her passions and interests, she became aware of another opportunity: to serve as a legislative aide to the president of the Oakland City Council, Ignacio De La Fuente.
Schaff was torn—the positions would take her down very different paths—but her love of her native Oakland and the idea of working with the City Council was just too intriguing. In addition, the job would utilize what she enjoyed most about her legal background: the ability to analyze and craft policy solutions.
So Schaaf made the pivot into government work. “What I love about the government is that you have both the privilege and the responsibility to look at the bigness, the comprehensiveness, and the interconnectivity of all of the issues that you care about. It’s hard sometimes because you have to make the tough choices, you have to analyze the trade-offs, but it also is very empowering because most problems are complicated, and they involve many levers in order to make meaningful change.”
Schaaf committed to the public sector, successfully running for Oakland City Council in 2010, and then in 2014 being elected as Oakland’s 50th mayor. With her election, many people approached Schaaf with their personal vision and their particular program for her to champion.
Oakland School Superintendent Antwan Wilson described his vision for more and bigger college scholarships and persistent support based on Future Centers, an in-school program pioneered in Denver, offering students guidance through the college application and financial aid process, and access to scholarship opportunities.
School Board and City Council members approached Schaaf as well, proposing to replicate a kindergarten-to-college initiative with roots in San Francisco that encourages college aspirations, removes barriers to saving for college, and starts family savings earlier by providing every child in kindergarten a savings account with $50. (While the city sponsors the initial contribution, local businesses, corporate and philanthropic foundations, and individuals provide additional funds and matching incentives for increased savings.)
The Walter & Elise Haas Fund proposed a Brilliant Baby program offering combined financial support and coaching for families with babies born into poverty.
Launching Oakland Promise
And then, as Schaaf puts it, “it suddenly came to me: All of these individual good ideas were components of a comprehensive great idea.”
With that realization, the bold vision for Oakland Promise was born. Launched in 2016, the comprehensive initiative aims to triple the number of college graduates from Oakland within the next decade by offering an interrelated series of programs that provide students and families with critical support from cradle to career.
As Schaaf notes, the need was clear, and she was positioned to convene and catalyze the collaboration needed to realize the bold vision:
I love, in particular, local government. I always say we fly at the right altitude because we live in the communities that we serve. We’re closer to the people whose lives we’re impacting, and so our decisions are informed every day by what we see and feel and touch in the communities that we represent. Right now, my ninth-grade class of public school students have only been getting 10 percent of that cohort through a college education by the time they’re 24. In this economy, that is unacceptable. It’s shameful. You cannot tell me that 90 percent of my children are not brilliant and talented and have incredible contributions to make to this region. I see this as my life’s work; this is the thing I am most passionate about.
Oakland Promise incorporates four initiatives spanning the period between the beginning of life and a successful launch after high school: Brilliant Baby combines college savings accounts seeded with $500 and financial coaching for parents; Kindergarten to Collegecombines a $100 college scholarship, savings incentives, and activities to instill a college-bound mind-set; Future Centers provides consistent support for a career and college plan, college applications, scholarships, and internships; and College Scholarships & College Completion offers financial support to address the cost barrier to attending college.
Early results of Oakland Promise are encouraging: Already, 700 former Oakland students and program participants are in college. Here are three insights from the program:
Embrace the bigness and the complexity | Often, complex coalitions with many different players representing different stakeholders have difficulty moving from concept to action. But Oakland Promise has built a robust coalition in a short period of time; every single elected official in Oakland has endorsed the initiative.
“I believe that often we fail because we aren’t ambitious enough,” says Schaaf. “I certainly have gotten some hesitation from folks because they worry that this is too much to succeed at, but most people actually see that you can’t be successful unless you truly take on the complexity and the comprehensiveness of what needs to be done to produce different outcomes.”
Leverage the power of combining grass tops and grassroots | The “secret sauce” behind Oakland Promise’s success is the combination of grass tops and grassroots, says Schaaf. At the grass tops, the steering committee is composed of institutions, donors, and top public officials, including the mayor, the executive director of the Oakland Public Education Fund, and the executive director of the East Bay College Fund.
The initiative engages the grassroots in two ways: as a connector and catalyst for existing implementation partners in the nonprofit and government sectors; and by organizing its own eyes and ears on the ground through the Oakland Promise Ambassador Program.
Design with the community, and set the context for local leadership and innovation | The reasons for grassroots engagement are clear to the mayor. “The fact that we don’t have all the talent and passion and capabilities at the table to advance the society means that we all lose. We’re never going to cure unjust inequities if the people who have suffered from that system aren’t at the table crafting the solution,” says Schaaf. With that commitment, Mayor Schaaf and the Oakland Promise team engage the Ambassadors as on-the-ground “truth tellers” who provide valuable feedback on the impact and communication efforts of the initiative.
Oakland Promise and its Kindergarten to College Program are about more than scholarships and savings accounts and even system changes. They are also about changing a belief that college is not within reach. It’s why each of the 16 participating schools has a team: the principal, a kindergarten teacher, a parent, and a community member tasked with devising its own college-going culture and supported by city-wide convenings, an ongoing learning community and partnerships with veteran schools. The bottom line is this: The local schools are determining their own path for creating a college-going culture.
That local initiative is creating results. Schaaf recalls the day she visited an elementary school for a bike-to-school day unrelated to Oakland Promise. (At this particular school 90 percent of the students speak a language other than English at home.) In a school district where in the past only 10 percent of students would be expected to complete college, and where one of her own staff members didn’t hear the word “college” as a student in the district, it was notable that as Schaaf walked into the building, she was mobbed by kindergarten students saying, “Mayor Libby, Mayor Libby, come take a picture with us in front of our K-to-college bulletin board!”