Since 2010, Joe Ross has served as executive director of Citizen Schools, California , a nonprofit that provides high-quality after-school and extended day programs to public school students in low-income communities, serving almost 1,000 students a day in five school districts. It’s a far cry from Ross’s previous jobs in military intelligence and as a corporate chief of staff, but it’s a mission with a personal meaning, and a call to duty he’s been well prepared for.
FAST COMPANY: How would you describe your role in Citizen Schools?
JOE ROSS: Compared to the business world, it’s like a general management role, or a command role in the military. I’m responsible for revenue and fundraising, driving strategy and trying to innovate and make everything work. As we’ve been asked to manage many more students, include special needs students and language learners, we realized that the people working for us needed to be amazing, and we needed to train them the way schools train new teachers. I latched onto the idea of providing a pathway to a teaching career for the people we were recruiting. I found an organization to provide credentials in California, pushed our development team to get grant money, and even though people thought I was crazy, we did it in four months. Now we have first-ever after-school pathway to a teaching career for college grads.
What has been the most unexpected turn your career has taken?
Probably joining the Navy. As an undergrad at Yale, I switched majors a lot, and accidentally completed the requirements for a political science major. I was drawn to international work, and an advisor suggested joining the Navy. Working in the reserves, he said, would get me a security clearance as well as training and credentials that would make it easier to get work in the government. Instead of the reserves, I decided to apply for officer training school and see what happened. I went to work for Paul Tsongas’s campaign and was about to start a job at the Lowell Sun, outside Boston, when I got a call from a lieutenant in the Navy saying I’d been accepted into the next class. I was drawn to the Navy in part because it felt more unknown and adventurous and challenging than anything else. I felt that this was a more interesting way to learn about foreign policy than being in an office in D.C. I could be a reporter whenever, but there was no way I would do this in four or five years. So I went off to Officer Candidate School in Pensacola, Florida.
How was the Navy different from Yale?
Coming from Yale, there’s a sense that you should free to do whatever you want, that you shouldn’t feel like you’re on a path ordained by someone else. People in the Navy are wired in a different way—they have an impulse to have work that matters in some way, to be at tip of the spear rather than in an office. This drives a certain type of personality. I graduated third in my class--No. 1 in physical fitness, No. 1 in academics. But I was horrible at what they call “military bearing.”
What were some highlights of your Navy career?
After school, I did intelligence training and deployed with various Marine units in Kuwait during Operation Southern Watch, reading the classified military Web and creating intelligence reports. I worked in Seoul in the Navy Analysis Branch, trying to predict when North Korea was going to sneak into South Korea via submarine. After meeting my wife, who is from South America, we went to live in Puerto Rico, where I ended up running multinational exercise with South American navies to train them in intelligence. That’s were I started to find opportunities to do innovation within the Navy. In 2000, I get a mandate to professionalize South American naval pre-deployment training, which involved setting up very realistic war games that changed the way they do their exercises. To be in the middle of the huge institution like the U.S. Navy, in my 20s, and being able to change these countries’ militaries in some small way—that was exactly what I joined the Navy for.
You went through several job changes after the Navy--were you following a master plan?
After 9/11, I stayed longer than the four years I expected to spend in the Navy. But then I got the point of feeling life is short and there’s a lot to do. I decided to go to grad school and continue with what I thought would be public policy/change-the-world type work. The Navy offered me the chance to do a Ph.D. program on their dime, but instead I applied to law schools—thinking it would be a great, flexible policy-oriented degree—and I got accepted at Stanford. I acquired a lifetime of student debt, and I had three kids by this time, so when I graduated I couldn’t really do a public-service-oriented job. Student loan repayment program are not designed for someone with three kids. I spent two summers at fancy law firms in the Bay Area, which made me realize I didn’t like being someone else’s lawyer.
I’d met a lot of business students when we were living in family housing at Stanford, and everyone was starting companies in 2006, 2007. I started getting the sense you could change the world with a startup. I had no background in accounting and finance, so I figured the way to learn that—and make a crazy amount of money, too—was taking a financial analyst job at Lehman Brothers. I worked in the Internet group for a little less than a year, modeling and pitching deals. I joined in summer 2007, and layoffs started in early 2008 when private-equity deals dried up completely.
Then you ended up having sort of an unusual position in the corporate world, right?
As the layoffs continued at Lehman, I rethought my plan. A neighbor who was a military retiree and had gone into business suggested I be a chief of staff to a CEO. I hadn’t heard of this kind of job in private business, but I typed “chief of staff” into LinkedIn and two jobs popped up. I got interviews at both. One of the companies was Pure Digital, which made the Flip video camera. I became the Smithers to the CEO, Jonathan Kaplan. I did all sorts of things—managing his schedule, taking out the trash—but I was also sitting in every meeting, learning a lot, and eventually negotiating or helping out with some pretty big deals, including the company’s sale to Cisco in 2009. After the company was acquired, I went to launch Flip in Mexico. That was exciting, going from nothing to something in that market.
Why drew you to Citizen Schools?
When I was going through the appointment process at Citizen Schools, I was often asked what motivated my move from business to education. I was frankly met with some skepticism, mixed with curiosity—is this military veteran business guy with a fancy law degree for real? What finally convinced them was talking about part of my own story that I’d never shared until I started in the nonprofit world: I was adopted. When I was five, my mother died suddenly and I went to live with cousins because my father was disabled. I got a new last name. I felt that this was totally unfair, but I also saw that the way to take some degree of control over my life was to go to college. I knew by the time I was in fourth or fifth grade that college was the ticket to being able to chart my way, choose my own name, be my own boss, take control over events. Citizen Schools is all about this--this idea that education is the path to being your own boss--in life if not in work. And my career has been all about this, too.
What skills from our previous jobs are most relevant to what you’re doing today?
I believe the perspective you get from jumping around, and the bravery you need to do that, gives you things that you need to innovate successfully in a company or a nonprofit. At the same time, when you have had a variety of experiences, it’s sometimes hard to know how to package that and figure out how to make a concrete contribution.
My ability to feel comfortable talking in Spanish or English to families we serve in high-poverty neighborhoods comes from the Navy, where you work with people from every kind of background you can imagine. I led teams of people who had not gone to college—that’s something I value and helped give me a real respect for people who may not have the usual brass rings but can be really unbelievable in ways you wouldn’t expect.
People often point to leadership experience in the military being transferable. Sometimes it is, sometimes it’s not. The military does give you a sense of confidence that you can walk through walls and deadlines can be willed into being achieved. So, I do have this sense that success is the only option—and I bring that to work in a lot of ways. But to be a good leader you also have to fall on your face at some point and just fail. Having more diverse management experience has helped me see my weaknesses firsthand and to own where I’ve needed to grow. I realize that here I need to lead in a way that’s collaborative and respects the culture of a nonprofit. You can’t always lead like an admiral.
Read about other members of Generation Flux:
Chris Caufield's Journey From NYPD Detective To Geico Gecko 
Ari Wallach's Career Solution: Become A Real-Life Problem Solver 
Adobe's Corporate Culture Through The Lens Of A Documentary Filmmaker 
MyEnergy CEO Ben Bixby's Eureka Moment Literally Involved A Light Bulb 
How IBM's Big Data Guy Found A Career In Chaos 
[Image: Flickr user Mathias Klang ]