Connecting service members with family, home, and country: Talking with Jessica Dolan of USO of Illinois

One of the best things about our profession is the opportunity to meet and collaborate with so many talented and interesting people at our clients and in the community. This Q&A series introduces some of the executives with whom we work and spotlights the ways they are leading and making their mark, both personally and professionally.

Jessica Dolan, regional vice president of USO, is a creative and motivated development executive with a history building financial stability and organizational capacity for non-profits. Since 2012, she has helped the USO advance its mission to strengthen America’s military service members by keeping them connected to family, home, and country, throughout their service to the nation. USO of Illinois touches the lives of more than 326,000 active duty, guard, and reserve military members and their families across the state. Its programs and services raise morale through unique recreational, educational, and cultural opportunities.

What do you want readers who are unfamiliar with USO to know about your organization?

When people hear “USO,” they think of shows to entertain the troops. We do that – but also so much more. Our programs support service members and their families from enlistment to deployment to transition out of the military and into civilian life. It is important to recognize that not just service members but also their families make sacrifices for our country. Family members can tap into an array of services, such as programming for children affected by the stress of separation from a deployed parent.

We continually expand our services. We have bricks-and-mortar centers in the United States and internationally. Those sites work with military leaders to understand and respond to the needs of the location – whether it is a guard base whose members are frequently deployed to flooded areas, a base with large units abroad, or a boot camp with mostly younger service members.

What is the biggest challenge in serving military members in Illinois?

As an organization, our biggest challenge is awareness. America has an all-volunteer force, with fewer than one percent of the population serving to protect our safety and freedom. Unless people have friends or family in the military, they don’t really understand what service entails and what members’ and their families’ lives are like.

From the perspective of my role, the biggest challenge is raising sufficient funds to deliver programs that support service members and their families. Supporting vulnerable populations like puppies and babies feels natural to people. They see our service members as heroes who embrace danger to protect us. It’s a hard dichotomy, but our heroes need support, too. We walk a fine line in communicating the spectacular contributions of this population while also explaining its need for our support.

What trends or opportunities for supporting our service men and women excite you most?

Approximately 70 percent of those who have joined the military in the Midwest since September 11, 2001, are in guard or reserve service roles. They don’t live on bases and are dispersed around the region, often in rural areas. Through a program called USO2GO, we create “pop-up” services to support those without access to USO centers. For example, Camp Dodge in rural Iowa provides weekend warrior training for more than 425,000 guard and reserve members annually. They travel in by bus from all over the United States. We created a USO pop-up center with free wi-fi, snacks, and information about programs ranging from transitions to financial literacy. It is now evolving into a permanent center.

As business and technology consultants, we are interested in how technology impacts non-profits and the communities they serve. How does USO use technology to further its mission?
Technology enables us to cross physical boundaries and provide assistance for members, wherever they are. For example, technology is integral to our USO Pathfinder program, which supports members over the 12 months before and after they leave the service. USO Pathfinder connects members with best-in-class resources in eight areas, such as legal aid, health and wellness, and use of VA benefits. Each member has a “scout” who serves as the guide throughout transition to civilian life. Members can use an app, powered by a Salesforce back end, to communicate with their scout and create a game plan. For example, imagine you are a soldier stationed in Kandahar, Afghanistan, returning from your final deployment in six months and then leaving the service two weeks later. You can sign up for Pathfinder at your base and then use the app to begin working with your scout on a plan for finding employment back home.

How can the Chicago business community engage with USO of Illinois?

USO is a quality charitable brand that people know and trust. Our association creates value and goodwill for our partners in the business community. Of course, we welcome gifts, but there are also so many opportunities to volunteer – from serving hot meals at USO Great Lakes to creating care packages for troops overseas to donating event tickets that we can disperse to members and their families. One key element of our mission is to bridge the civilian-military divide, and volunteering is a great way to do that.

What is your favorite thing about living and working in Chicago?

I love it all, from the lake with so much protected waterfront space to the great food to the ability to get anywhere on the train. It’s hard not to look around every day and marvel at the general splendor of it all – particularly now, in the fall, when the leaves are changing, and the city is at its best.