A tireless dedication to charting a course for top-notch transportation that not only helps students but their families as well has made John Hennessey stand out among his colleagues. 

Hennessey, the director of transportation for Worcester (Mass.) Public Schools, has spent the last three-plus decades making student transportation ever more efficient in Massachusetts and helping his colleagues do the same. 

He has been described by colleagues as a “problem-solver” with a strong work ethic who leads with compassion but holds his department to high customer service standards.

Brian Allen, the chief financial and operations officer for the school district and Hennessey’s supervisor for the last nine years, adds that his employee “must have been very good with puzzles growing up.”

This was particularly evident when Hennessey helped a struggling school district get the arrival times for its bus routes back on track, using the routing expertise he gained as a public transportation employee. Twelve years later, he brought that know-how to his current district. 

“He has an ability to see the tier schedule and fleet schedules in a three-dimensional way and seems to enjoy each challenge that he faces,” Allen adds.  

Drew Damien, the director of transportation for neighboring Palmer Public Schools, says that Hennessey’s “unbelievable knowledge base and thoughtful attention to every detail make him an extraordinary leader, mentor, and colleague.”

For his devotion to transporting students safely in Massachusetts and beyond, School Bus Fleet has named John Hennessey its 2019 Administrator of the Year. SBF Executive Editor Nicole Schlosser presented the award at the National Association for Pupil Transportation Trade Show in Columbus, Ohio, on Nov. 5.

Mapping a District’s Transition

Hennessey began his career on the public transit side of the transportation industry, following in the footsteps of his father, who worked for the Massachusetts Bay Transportation Authority (MBTA). In 1976, when the state created regional transportation authorities to pick up some of the MBTA’s routes, Hennessey took a job with the Lowell (Lo Law) Transit Management Inc. as a part-time bus driver while attending college. He soon worked his way up through the ranks, becoming a starter, then part of office supervisor staff as a scheduler. 

A pivotal point in Hennessey’s career occurred in 1987. Lowell Public Schools was struggling to accommodate an influx of students due to demographic shifts and a desegregation program that was established by the district, the Massachusetts Department of Education, and the state court system. The district needed help transitioning to the enrollment increase and a new routing software program — all without the direction of a transportation supervisor, which resulted in some challenges as the new school year started.

“Part of the problem was there weren’t enough school buses on the road, part was [staff members] didn’t know the routing program, and the routing software company wasn’t familiar with the city,” Hennessey explained. “So there were times when kids weren’t getting picked up till 6 or 7 at night.” 

In addition to drivers from Buffalo, N.Y., coming to Lowell to assist, the Lowell Regional Transit Authority stepped in to help and volunteered Hennessey’s services as a Lo-Law transit router to the district’s transportation department. His analytical skills were put to good use when he worked on the routing system. 

The planned two-week assignment stretched into four weeks, and then he had to return to his job.

He took his skills over to the pupil transportation world permanently when he learned that a transportation coordinator position was available. He applied and was selected for the position, starting it on March 15, 1988. 

The first task Hennessey tackled in his new position at Lowell Public Schools was creating a tiered schedule to ensure the buses kept running smoothly into the upcoming school year. He met with all the stakeholders involved, including school principals, administrators, and union leaders on a schedule. He also worked closely with programmers at Roger Creighton Associates school bus routing software (which is now Tyler Technologies’ Versatrans transportation management solution) and, with the district acting as the beta test site for the supplier’s modules, would provide feedback.

In 2000, Hennessey would begin traveling another route on his career roadmap: He began working for Worcester Public Schools after learning of a job opening from a retired colleague he met through an association — one that he cofounded.

“We have to understand that people depend on us every day and we have to earn that trust every day.” 

John Hennessey, director of transportation 

Worcester (Mass.) Public Schools

Building Association for Guidance

Hennessey was a founding father of the Massachusetts Association of Pupil Transportation (MAPT), which was officially established in 1990. (He served as the association’s first president.) Providing a firm foundation for the association ever since, Hennessey took the helm two more times, from 2004 to 2006 and from 2010 to 2012, and served as vice president and region director while in Lowell from 1988 to 2000 and Worcester from 2000 to 2019. 

“Although he is no longer a board member, he continues to advise the board and his contributions and knowledge are invaluable,” says Colleen Cavanaugh, the director of planning and operations for the MAPT. 

MAPT hosts speakers from Massachusetts Registry of Motor Vehicles, industry thought leaders such as Dr. Linda Bluth, and Dr. Peter Lawrence, and representatives from the Pupil Transportation Safety Institute to share information with its nearly 100 members. 

“We try to make MAPT an education resource for all of our members,” Hennessey says. 

Hennessey has also served on a task force created through the Massachusetts Legislature since 2004, which addresses the various challenges and aspects of special education transportation. 

The task force aims to enhance coordination between districts, for example, with vehicle sharing for cost benefits and to address the driver shortage. In some cases, the practice can also help students with socialization, preventing them from having to ride the bus alone. 

MAPT was awarded a contract through the task force to coordinate a program that evaluates district operations, and has suggested ways to streamline, saving them tens of thousands of dollars, Hennessey says.

Laying the Groundwork for Success

Worcester Public Schools transports about 12,000 students on more than 200 vehicles to several special programs in addition to school and home. The transportation department accomplishes this complex and often challenging feat with a three-tier district schedule, making 5,000 transportation route changes per year. That equates to nearly 30 route changes per school day), Allen says.  

“Each change has a ripple effect on multiple buses and student pick-up times, and John approaches each issue in an amazing way,” he adds.

The district operates about 50 of its own conventional and special-needs buses but has historically contracted out some of its service (that number is currently 136 buses). As the contract to operate athletic and field trip buses neared expiration and the district received no bids, Worcester Public Schools took on those as well as all 11 home-to-school routes, as enrollment has increased once again, Hennessey says. (The district has since renewed a contract with its vendor for bus service through the end of the 2021-22 school year.) 

At press time, a district-appointed School Committee is looking into bringing the entire school bus operation in-house, thanks to Hennessey’s hard work. 

More recently, Allen says, Hennessey suggested developing the district’s internal capacity to run all of its own transportation. After two years of study, research, and building that capacity, the committee is deliberating a plan that would allow for full district-operated transportation in two years. The change in operation is expected to improve customer service and provide $30 million of cost savings to the district over the subsequent 10 years, Allen adds.  

“Should this plan be approved and implemented, it would clearly be a career-defining endeavor,” he says. “This bold recommendation highlights John’s work ethic and problem-solving, all intended to improve student transportation for the district.”

Traveling Above and Beyond

Upon arriving at Worcester Public Schools, Hennessey noticed a message on the human resources director’s bulletin board: it said “Inconvenience yourself.” That stuck with him, he says. 

“Go just a little bit beyond, because who knows how much better you could make things for someone else?” he adds.

Cavanaugh, who has worked with Hennessey on the task force as well as MAPT, adds that he “always puts the students in his care first and goes above and beyond to provide a high level of quality service."

Hennessey has served for nearly two decades on the task force, and is always available to help his colleagues and offer advice, Cavanaugh says.

"His knowledge in the field of school transportation is beyond reproach,” she adds.

That devotion extends beyond state boundaries: he has also visited districts in Minnesota (Minneapolis Public Schools) and Georgia (Savannah-Chatham County Public School System) to learn about maintenance facility options and bringing bus service in-house, respectively. 

Allen adds that he thinks of Hennessey as the district’s voice of student safety. 

“He is constantly reminding us of proper school bus stop locations and safety zones around the bus,” he says.  

Of his career, Hennessey says he loves the challenge of getting the job done not only for the students, but for their entire families, because they build their schedules around getting their kids to and from school. 

“We have to understand that people depend on us every day and we have to earn that trust every day,” he adds.