Upward Bound director receives national award honoring decades of service

UNIVERSITY PARK, Pa. — When Leo Conway took his first summer job with an Upward Bound program in 1990, he had no idea it would shape his career. That early experience — combined with the impact of Upward Bound programming and strong connections with educators and community members — helped guide Conway’s professional path.

Conway joined Penn State’s Upward Bound staff in 2017 after spending many years at St. Francis University. Today he is director of Upward Bound Programs at the University.

Now, after decades of outstanding service and work with thousands of students, his leadership is being recognized with a TRIO Educator/Leader Award. Presented at the National Legislative Conference, the award honors Conway’s extensive service and leadership within the TRIO system.

A shift in plans

Conway began his career as a high school math teacher, describing himself as a “math nerd” who expected to teach for life. His plans completely shifted in 1990 when he took a summer position with Upward Bound.

“I discovered TRIO and Upward Bound programs and that all changed,” Conway said.

A chance encounter with a professor during spring break led him to interview with Upward Bound Director Denise Kovatch.

Conway said he had a positive experience and felt like he could talk to the program director “all day long,” but still thought that he had messed up the interview. As luck would have it, he said, the team thought he was great, and he got a call for a job that summer. He continued to teach high school and worked summers at Upward Bound for about 8 years, until a full-time opportunity with Upward Bound in 1999 opened new possibilities.

“I was considering leaving full-time teaching. My entire life I wanted to teach trigonometry and calculus and that’s exactly what I was doing at the high school I was at,” he said.

Over time, Conway said, he had noticed differences in how students were supported and prepared in both high schools and in the TRIO programs. The impact of Upward Bound stood out to him.

“Then I thought to myself, well then why not move to Upward Bound. So that’s exactly what I did. I quit the profession that I thought I would be in the rest of my life and began my TRIO journey, and I have never regretted it since.”

A journey to leadership, and service

After transitioning to a full-time role, Conway spent about 18 years at St. Francis before joining Penn State as associate director of TRIO Upward Bound Programs in 2017. He has since taken on additional leadership responsibilities and now serves as director, while remaining active in state, regional and national TRIO associations.

TRIO programs support low-income, first-generation, and disabled students, with Upward Bound serving high school students in grades 9 through 12. The program currently partners with nine school districts across Pennsylvania.

Trio has evolved throughout the years, Conway said, from an organization that served only high school students, to one that now extends resources from 6th grade through the doctoral level, as well as to adults who are returning to or starting post-secondary education.

Conway’s leadership roles have been widespread across different TRIO associations, including serving as treasurer for the state association PA TRIO, the regional association MEOP (Mideastern Association of Opportunity Personnel), and the national TRIO association COE (Council for Opportunity in Education), as well as holding presidential positions in both state and regional associations.

Despite these roles, Conway said, he views his work through the lens of service.

“In terms of working for Upward Bound I always saw that participating in leadership across all those associations ... I got to really network with lots of TRIO folks who now, many of them, are certainly still my colleagues but are good friends of mine,” he said.

“And even as director I don’t see myself as the leader, it’s more about service that we are giving to our students and in my role of course, making sure that staff is being served as well," he added.

He also emphasized the importance of his team as a key factor to Upward Bounds success and his accomplishments as a leader.

“I really thank the Upward Bound Programs team because you know, when all these meetings and things happen … I take off to the meetings, and they keep the programs really running while I’m away,” he said. “I have total faith in all of them… I know that the programs and our students are in very good hands.”

Memorable experiences

Along with serving and helping to ensure access, Conway said his time spent in Upward Bound has provided a lot of positive experiences. His favorite memories from his time include both the professional and the personal. Two of the top contenders for best memory were taking his students to Niagara Falls and meeting acclaimed actress Viola Davis.

Conway attended a national TRIO conference where he got to meet Davis, actress and a prominent alumna of the TRIO Upward Bound Program, which was a huge professional highlight for him.

“I got to meet Viola Davis and shake her hand and just talk for a couple minutes… it was absolutely fantastic,” he said.

Davis and her sisters were enrolled in Upward Bound programs and have previously noted their experiences in the program as highlights in their lives that directly related to their success. The teachers and educators in the program made a huge impression on the sisters, Conway said, who were dedicated and tenacious students.

Conway said he feels that his students enrolled in Upward Bound really are dedicated as well, which is why he really enjoys celebrating the end of each summer program with a student trip. He noted that while many students are out celebrating summer, his Upward Bound students are waking up early, giving up summers, and giving up Saturdays during the school year.

“One of my best memories was just a few years ago, we took the students to Niagara Falls… We got to ride on the maid of the mist… that’s my number one destination for upward bound summer trips," Conway said. "Those end of the summer trips are always so special because they’ve worked so hard during the summer.”

A commitment to educational equity

While TRIO programs have expanded significantly — now serving students from middle school through graduate education — they also face ongoing challenges, Conway said, including potential federal changes.

“We’re really fighting for survival with what’s happening at the national level,” Conway said.

The work Conway leads reflects Penn State's broader commitment to educational equity, he said, aiming to ensure that financial and opportunity gaps do not determine who accesses or completes higher education.

"Leo Conway exemplifies what dedicated, student-centered leadership looks like in practice," said Seria Chatters, interim vice provost for Educational Equity at Penn State. "Under his direction, Upward Bound has become a powerful bridge — building pathways to post-secondary opportunities for first-generation and economically disadvantaged students, wherever their educational journey takes them. His work, housed within the Office of the Vice Provost for Educational Equity, reflects our shared commitment to ensuring that a student's zip code or family income does not determine their future."

Conway said programs continue to move forward. Upcoming six-week summer academies are planned across multiple Penn State campuses, including at Penn State University Park, Altoona, Greater Allegheny, Beaver and Brandywine.

As the program evolves, Conway said his focus remains unchanged.

“Our goal is to help our students while they are in college," he said. "A) that they get into college and B) that they have some tools in their tool kit … to make sure they complete college and get their degree.”