The Mechanics

of Grant-Making

By Rebecca Cherin, Managing Director of Programs


I haven’t always been a grant-maker…

Before Tipping Point, I had a career in direct service, helping young people achieve their high school diplomas or GEDs, and pursue their vocational or career aspirations. When I went back to grad school, I realized that I had always been on one side of the funding table. I had long tried to educate funders about the programs we ran and the impact we made, and I was intrigued about what it might be like to be in their shoes. Back in 2006 when I first got the job at Tipping Point, I was the grant-making team. Today, I’m proud to lead a team of 12 dedicated, remarkable people. As we celebrate a decade of Tipping Point this summer, I’m confident that we are doing the best work we’ve ever done. In honor of 10 years of growth and learning, here’s a quick look at 10 aspects of our current grant-making structure.

  1. We hire for passion and experience. Much of the current program team has worked directly in the areas of education, employment, housing or wellness prior to Tipping Point. Three of us have worked for or run operations at Tipping Point grantees at various points in our careers, while others (like Senior Program Officer Karina Moreno) came to us from grant-making roles with other funders we admire.
  2. We’ve specialized as we’ve grown. What was once a small group of individuals overseeing a portfolio of individual grantee relationships has evolved into a team with distinct sub-specialties. Over the past several years, we’ve built out both our Impact + Learning team and the Strategic Partnerships department within programs.
  3. Our senior program officers are organized by region. Here in the Bay Area, poverty exists in all geographies and there are pockets of concentrated need in virtually every direction. Because each of the six counties we serve has its own mix of urban and suburban parts, distinct history, and set of government, business and non-profit players, our team is structured so that we can build relationships and knowledge at a hyper-local level.
  4. We invest in leadership above all else. In my decade of grant-making, there is nothing more telling or effective than sitting down with an organization’s leaders to hear from them firsthand. We look for vision, a grounded sense of the community’s needs, the ability to admit inevitable challenges, and a hunger to continuously improve.
  5. We support efficacy before scale. Grantees often feel pressure to grow in response to funders who say, “Serve as many people as you can, as quickly as you can.” At Tipping Point, we believe that it’s more important to know what works first, then scale. We go to great lengths to help each grantee intimately understand the ins and outs of their model, articulate what it takes to optimize it, and seek out the organizational capacity needed to execute well before expanding further within the Bay Area or nationally.
  6. We prefer depth over breadth. Our board and team are aligned in a philosophy to make deeper impact with fewer organizations rather than adding more and more grantees to extend Tipping Point’s reach. We hope that in the next three to five years, we can continue to help our groups gain an understanding of efficacy on their way to serving more people in the Bay Area. This also means that we plan to significantly increase grant sizes to existing grantees and be more deliberate about sequencing our management assistance to see if we can accelerate growth.
  7. While often high-risk, early stage investments are critical to breakthroughs in our sector. We recently had the chance to visit Tipping Point grantee Caliber Schools and were struck by the thought that just two years ago, we were sitting around a table with the founders, talking about the plan and vision, and our potential investment. At the time, Caliber didn’t have a charter to operate or a school. It’s truly incredible to see its campus and students thriving today, to hear about the impressive initial impact and waitlists for next year. In a short time, Caliber went from a sketch of an idea to a living, breathing ecosystem, which serves communities in West Contra Costa desperately in need of more great schools.
  8. Our work truly takes a community. We’re fortunate to have an ever-expanding list of partners who serve as an extension of our program team, contributing $2M+ in goods and services each year to grantees beyond the general operating grants we issue. With their support and the vision of the program team, we’ve built out our grantee offerings to include strategic planning, executive coaching coupled with peer support, and opportunities for networking across the portfolio.
  9. The ultimate goal is client-level impact. Thanks to support from McKinsey & Company and the work of the Impact + Learning team, we’ve refreshed the way we measure the impact of grantees and sharpened our focus on the outcomes that put people on a pathway out of poverty. We’ve synthesized our learning about organizational growth trajectories and the time it takes for a non-profit to go from achieving impact with 400 students locally for example, to 8,000 students nationally. By defining these stages of growth and collecting data that indicates progress for clients within each one, we are confident that the outcomes we’re able to report now are as clean, and more telling of our true impact than ever before.
  10. Grantee relationships are the heart of our work. Even as we’ve added more people to the team and our portfolio has grown, I’ve held the belief that as managing director, I should always continue to hold at least one grantee relationship. My role as direct liaison to First Place for Youth, one of Tipping Point’s very first grantees, keeps me grounded in the work. We’ve also recently added a series of events we call Lunch with Leaders, where we invite grantee staff to the office to eat with the whole Tipping Point team and share their insights. And we are always looking for feedback — we hope that grantees, donors, and newcomers to the Tipping Point family feel comfortable asking us why we do things and weighing in on how we can improve.
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