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Paul Osland Named First Student President
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Paul Osland Named First Student President

September 4, 2019

First Student today announced that Paul Osland has been appointed as the new president of First Student. In July, he was named interim president upon the announcement of Dennis Maple’s departure. First Student is a division of First Student.

“I am delighted to announce the appointment of Paul Osland as president of First Student,” said First Student Chief Executive Matthew Gregory. “I know that Paul will be able to build on the progress achieved in the business to date, including a return to revenue and fleet growth and the development of industry-leading safety performance. This will enable First Student to achieve its full potential alongside First Transit in the North American mobility services sector.”

Osland joined First Student in 2016 as chief operating officer. In this role, he was responsible for the overall day-to-day operations of the organization.

“I’m excited to be taking on the role of president at First Student,” said Osland. “I’m very proud of the visible progress the team has made over recent years and look forward to continuing this work into the future as we build on the market-leading platform we have established.” 

Since he joined, Osland has contributed extensively to the improvement of First Student through his operational leadership and the delivery of a number of key business improvement initiatives.

He has focused on strengthening the operating structure and continuing to build an emphasis on process discipline, helping First Student achieve excellent contract retention rates, record customer satisfaction scores, and leading employee engagement scores. As a result, First Student is growing again, both through an increase in market share and acquisitions.

Prior to joining First Student, Osland worked for Chicago Public Schools (CPS) as both chief facility officer and executive director of transportation. Before joining CPS, Osland held a variety of commercial and operational leadership roles, including positions within Fortune 100 companies.

First Student is the largest school transportation provider in North America, transporting more passengers per day than all domestic airlines combined.

About First Student, Inc.
As the leading school transportation solutions provider in North America, First Student strives to provide the best start and finish to every school day. First Student completes five million student journeys each day, moving more passengers than all U.S. airlines combined. With a team of highly-trained drivers and the industry’s strongest safety record, First Student delivers reliable, quality services including full-service transportation and management, special-needs transportation, route optimization and scheduling, maintenance, and charter services for 1,100 school district contracts. For more information, please visit