David Drucker
Assistant Vice President
Student Life & Dean of Students
Dean College
David Drucker
Assistant Vice President
Student Life & Dean of Students
Dean College
Over the course of the 13 years that Jon has been with Kiessling Transit, he has held many roles and taken on a variety of responsibilities. Essentially, Jon’s path has paralleled the trajectory of the company. As Kiessling Transit has transformed and grown in the past decade into a leader within the transportation industry, so too has Jon developed from an IT professional and office administrator at the company to a key executive of the organization.
Jon is both a longtime friend and employee of the Kiesslings, having joined the company in 2004. At the time of his hiring, Kiessling was entering into a new MBTA RIDE contract that required a fully dedicated IT person to manage all facets of the company’s technical infrastructure, systems and support. The Kiesslings hired Jon for this critical role for many reasons, including his expert problem-solving skills, his ability to effectively streamline business practices, and, most important, his collaborative and easygoing demeanor. During Kiessling’s contract management of the MBTA’s THE RIDE services on the South Shore, Jon was solely responsible for managing the Wide Area Network (WAN) installation connecting Kiessling’s Norfolk location with the MBTA’s 10 Park Plaza offices in downtown Boston. Jon has also successfully led a number of company projects, with a heavy emphasis on software migrations of multiple company on-premise systems ranging from Microsoft Exchange/Office365 to cloud based Payroll/HR solutions, many which trimmed annual company IT costs significantly.
Today, as Vice President of Operations, Jon works in lockstep with the Kiessling owners, Lars and Roger, and, with great attention to detail, he oversees all the day-to-day operations at the company. His responsibilities include investigating, recommending, installing and upgrading all company software and reviewing company backups of all databases. Jon’s quick thinking and response time, as well as his proactive IT planning, mean that equipment downtime and other operational issues are kept to a minimum.
It’s truly exciting to see the impact that my team and I have had on improving the practices and processes at Kiessling and at our partner companies. Our goal is always to go above and beyond to help our clients accomplish their desired goals. I look forward to helping you make positive changes at your place of business and a genuine difference in the lives of the people you employ and serve.
Before joining the Kiessling team, Jon was already an accomplished manager, operating internal IT departments and new system rollouts. He has held technical roles at a variety of Massachusetts-based companies, including serving as a systems administrator in the IT departments of both Centra Software Inc. (now SABA Software), in Lexington, MA, and TJX Companies in Framingham, MA. He was also a technical recruiter at Judge.com, previously located in Needham, MA.
Jon grew up in Walpole, MA and now lives close by in Wrentham, MA. He earned a Management Information Systems degree from Salve Regina University in 2000.
While leading the operations team at Kiessling is a consuming job, Jon makes sure to build in time for his family, friends and sports. He devotedly coaches his sons’ athletic teams and loves the opportunity this gives him to watch them grow on many different levels. Jon’s other favorite pastimes include attending concerts and Patriots games, enjoying local restaurants, and playing many, many rounds of terrible golf!
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