Not in My Backyard

Nonprofit CEO Jennifer Loving has developed relationships with tech companies to take on Silicon Valley’s most vexing issue—homelessness

By Jackie Krentzman

When Jennifer Loving was growing up in Southern California in the 1970s and ’80s, her uncle was a “fire-and-brimstone” minister. He ran a church in Venice Beach that served as a haven for the many homeless people who flocked there.

“He took in anybody who needed a place to stay, no questions asked,” says Loving, who today is the CEO of Destination: Home, an affordable-housing nonprofit for homeless people in Silicon Valley. “So I grew up thinking that if someone needed a place to live, the logical thing to do is make that happen.”

Today, Loving is making that happen in a big way. She has led the countywide charge to build supportive housing for many of the more than 7,000 homeless people in Santa Clara County, right in the heart of Silicon Valley. Destination: Home is a convener of supportive-housing nonprofits, government officials, and the private sector, which work together to create permanent housing for the homeless. Since 2015, Santa Clara County, in large part because of Destination: Home, has housed more than 5,000 formerly homeless people.

Loving saw lots of dollars being wasted on trying to solve homelessness—much of the waste due to lack of coordination among the different entities working on the problem—and realized the answer was a public-private partnership, with nonprofits, the tech sector, and city and county governments working together to tackle what is perhaps the most vexing issue facing the greater San Francisco Bay Area today.

Loving, who is impassioned, relentless, and strategic, has built these public-private partnerships both through her force-of-nature direct appeals and through her commitment to a collective impact theory of change. Her persistence and vision are paying off. In March, Cisco gave Destination: Home one of the largest grants ever to a homeless organization: $50 million.

Diversity Woman: Besides your experience at your uncle’s church, what led you to devote your life to sheltering homeless people?
Jennifer Loving:
 I went to college to study counseling, but I quickly realized that wasn’t for me—I didn’t want to spend my time with someone to help them quit smoking or resolve a bad relationship. So I interned at a battered women’s shelter in Southern California, and I saw firsthand what it meant to be homeless. I also learned how having a home was an anchor for everything, especially as it relates to violence against women.

After graduate school [at Cal Poly, San Luis Obispo], I went to work with the homeless and have stayed there. This work is part of my roots, and over time I learned to understand the issue from a social justice perspective—homelessness is the end of a dirty river filled with racism and abuse.

DW: How did you learn to run a nonprofit?
JL: I began on the front lines in my 20s working with people who were dying. At the time, I was at an organization with a lot of heart but not a ton of business sense. So they gave me a lot of rope, and I was tasked with opening a new homeless shelter. I was only 27 years old and I thought, “How do I do that?”

I figured it out, and in a few years I had progressed from shelter worker to COO of a $16 million organization. Then, the CEO quit and the board put me in charge at a time when there was a 95 percent certainty the organization was going to go bankrupt and close. I was tasked either with making it work or closing it down.

I didn’t know what I was doing, but I was able to assemble a team, and through a process of raising enough money and having a lot people help, the organization ended up solvent.

The key was having the right people and staying true to your North Star, which for me comes from getting really pissed off! I did not want to see more people homeless because we messed up.

DW: What leadership lesson did you learn early in your career?
JL: For one, I learned the very important lesson that everything is possible. I also learned how to work with men. Pretty much everyone I had to deal with to get projects off the ground were men. At first, people thought, Who is this young girl? 
I literally would be called that. Overcoming that attitude by men and succeeding have always been part of my motivation.

DW: In 2010, you became CEO of Destination: Home. Today, it has made tremendous strides in what was considered an intractable issue. How did you get there?
JL: We did it by utilizing what is known as the collective impact theory—which was happening a lot in our backyard, at Stanford. This means, in short, that large social problems can’t be solved if there is just a singular owner to a solution. You need multiple owners, across sectors, coming together. At Destination: Home we came up with the idea of creating public-private partnerships—getting the local companies and 15 cities in Santa Clara County to work with nonprofits on using our joint resources to solve this issue.

DW: You quickly got corporate buy-in, and recently Cisco gave you an astounding $50 million grant. What motivated Cisco to do this?
JL: It is the largest commitment from a tech company to solve homelessness I ever heard of. What Cisco is doing is extraordinary. I think that, simply, Chuck Robbins, Cisco’s CEO, gets it. He believes tech companies have a responsibility to be good community partners and neighbors. He understands that no one can build this housing on their own—it is way too expensive—and so we need the involvement of private companies to make this happen. Cisco stepped up.

Hopefully, Cisco’s example will lead to a lot more tech companies giving to homelessness. Fifty million dollars is amazing, but we need a lot more—hundreds of millions of dollars more. Thankfully, Chuck has been helping us deliver that message.

DW: Is serving as a CEO in the nonprofit sector different than in the private sector?
JL: Totally different—the difference is when you don’t have a product people want to buy, or a way to make money, it is harder. You need to have a mission focus, as well as run your nonprofit like a business, with bottom-line responsibilities. However, that is challenging, as you don’t have the same revenue sources.

DW: What have you learned from corporate leaders that has informed your work?
JL: I learned that you have to have a way of proving your progress. Plus, you cannot be afraid to ask for what is necessary. When I asked Cisco for this money, it was necessary. Finally, as a leader, I discovered that I am not afraid to be wrong; 
I am not afraid to course-correct.

DW: What advice do you give aspiring leaders?
JL: Find what is really important to you. I am so grateful for the people who are working to save barrier reefs, but that is not my thing. Find your thing, and then build a team around solving whatever that problem is. Make sure that everyone has the opportunity to contribute his or her skills and resources. It is not about one person. It is about creating a container for a community or organization or company to act. DW

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