Meet Our Team

William Shean

Boston Operations Manager

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William has worked at Kiessling Transit since 2014, which makes him one of the newer kids on the block. However, William has gained a lifetime’s worth of transportation industry knowledge from the very experienced people he has worked with. He credits these many mentors at Kiessling Transit with teaching him not just about being a great employee or manager, but also about being a better person.

William originally began his career at Kiessling as a Boston dispatcher, but was such a quick learner and hard worker that he was promoted to Boston Operations Manager within a few years. He also currently serves as a technology administrator.

As Boston Operations Manager, William’s primary responsibility is to assure the safety of all passengers as well as our fleet employees. He also works closely with the directors and managers of the programs and groups we serve to ensure that any issues are resolved quickly and effectively and to make sure that all passengers are transported on time and in a professional, kind manner.

Whether it’s a question, a requested change or a concern that needs to be addressed, William will go above and beyond what is expected to ensure total customer and passenger satisfaction.

William is also known for bringing a high level of energy to the job, day in and day out, and setting a very positive tone for everyone here at Kiessling. In addition, he has a very generous spirit and gives liberally, whether it’s as a volunteer coach for a high school sports team or simply being that friend you can always count on.

In 2015, William graduated from Quinsigamond Community College, Worcester, MA, with a degree in Computer Science. Most of his childhood was spent in Uxbridge, MA, and he now lives in Hopedale. Outside of work, William loves to travel and meet new people. However, on Sundays in the fall, he’s just fine being a couch potato, hanging out with friends and family, and watching football.

Ryan O’Connell

General Manager

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Ryan is considered a relative young’un at Kiessling Transit as he joined the company in 2011. He came onto the team as an IT Support Admin, bringing with him experience as an inspector for FST and multiple years in the sales industry. Ryan proved, in just a short while, to be exceptional in people skills and problem-solving, and has demonstrated a unique ability to motivate others and to adapt and be flexible in any situation. Now, as General Manager at Kiessling, Ryan is responsible for the day-to-day operations of the company and for resolving any issues that might arise, whether it’s technology- or people-related.

Working at Kiessling is really a perfect fit for Ryan because serving the special needs population has always hit close to home for him. At Kiessling, he has the opportunity to help all individuals and families have equal access to transportation and to provide them with true compassion and understanding.

In a day and age where you can do almost everything via your computer or phone, Ryan takes pride in keeping the human element alive in every service and experience Kiessling provides.

In addition to being the quintessential people-person, Ryan is very interested in history, philosophy, music, and all things sports, including golf and trap shooting. He also is a pet parent to “Bo,” a rescued American Staffordshire Terrier, who he and his fiancé are working on training. Ryan is an advocate of many organizations, but two non-profits, in particular, have his heart – NEABPD and Autism Speaks. He hopes to continue to educate more people on the disorders that effect so many people worldwide, but that we still know so little about.

Roger Kiessling

President

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Just like his brother Lars, Roger grew up around the family business, and took a similar path through the company. Since 1985, Roger has served in various functions at Kiessling, from janitorial, to monitor and driver, to project manager.

Roger’s first full-time role with the company was no small undertaking. He was tasked to to manage the start-up for a whole new territory of service for the MBTA and to oversees enhancements to the company’s Braintree facility in order to support this new business. The fact that the operation was up and running effectively from day one is a testimony to Roger’s unparalleled operational skills.

For the last 20 years, Roger has played a major role in all of Kiessling’s new route mobilizations, including managing vehicle and equipment delivery, overseeing hiring and training of personnel, monitoring service quality levels, assuring regulatory and contractual compliance, and acting as liaison with transit authorities and advisory groups. Over the past two years, Roger led two of Kiessling’s most significant start-ups – Demand Response services for the MetroWest Regional Transit Authority (MWRTA) in 2015 and Fixed Route services for the MWRTA in 2016.

Throughout his Kiessling career, Roger has been exposed to all facets of the paratransit business and, in total, has been responsible for an average of 300,000 trips per year over the course of seven years.

While Roger has never completely left the transportation industry, he did take a brief hiatus from Kiessling to sail tall ships around Boston Harbor. The boats he captained include the Voyager II and Doc Edgerton for the New England Aquarium, the Schooner Liberty, and the Admiral’s Lady.

Originally from Walpole, MA, Roger now lives in Maine with wife and family. However, since becoming President of Kiessling, in 2017 you are most likely to find Roger hard at work in our Norfolk, MA office as well as our Framingham, MA MWRTA office supporting any new contracts, rolling out innovation ideas, and ensuring that our daily operations are running smoothly.

Matt Vieira

Worcester Operations Manager

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You could say Matt owes his successful career at Kiessling to his mom. Mrs. Vieira had worked for Kiessling and had a very positive experience, so when Matt wanted to make some extra money in college, he applied for a dispatcher’s position with the company. Now, 10 years later, as Worcester Operations Manager, Matt demonstrates daily his excellent skills in route creation, data retrieval, analysis and upkeep, and problem-solving.

Prior to joining the Kiessling team, Matt worked at Adams and Adams Building Services , Inc. as a Service Tech.

Matt graduated with a degree in Mechanical Engineering and he remains completely enamored with all things related to technology and science. His favorite things to do when not at work are learning something new in either field, buying a new piece of technology, or working on a project, like building a custom computer! Matt’s other interests include 3D printing, wood carving, and reading.

Matt supports the Wounded Warrior Project, which is a terrific foundation that supports veterans and service members that have been injured in the line of duty. He grew up in New Bedford, MA.

Leonard Scarano

Safety Manager

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When Leonard retired from the United States Postal Service (USPS) in 2004, he moved to Florida and intended to enjoy the rest of his non-working life in the sunshine state. However, Florida never really felt like home nor did retirement feel that comfortable, so Leonard moved back to Medway, MA and applied for a position as a driver at Kiessling Transit.

Over the next several years, Leonard distinguished himself by thoughtfully assessing situations, creating thorough plans of action, and implementing his ideas quickly and effectively. Plus, he demonstrated an incredibly energetic and enthusiastic personality. These skills and traits were exactly what Kiessling was looking for in a Manager, and so Leonard was first promoted to a General Manager role and then eventually to his current position, Manager of Safety and Training.

Leonard’s role at Kiessling is critical to the company’s success. He is responsible for ensuring the safe, efficient, and pleasant transport of the individuals entrusted to our care.

Leonard gained invaluable experience supervising people when he worked for the USPS, where he started as a letter carrier but was later promoted to a managerial position. He has overseen several different USPS locations in the Boston area, both clerical and carrier operations, and hundreds of postal staff members. At USPS, Leonard received several Superior Achievement Awards, including one in 1984 for Letter Carrier and another in 1989 for Supervisor.

According to Leonard, being a good listener and always remaining very sensitive to people’s needs is an essential part of being a great manager no matter where you work, but especially in the transportation industry.

Outside of work, Leonard spends much of his time doing physical activities, like hiking trails with his dog and traveling throughout the East Coast. Dogs have always been prominent in Leonard’s life and he cannot recall a time over the past 40 years when one wasn’t by his side. Leonard earned a Canine Obedience/Training Certification from Mount Ida College, Newton, MA and has trained dogs for obedience and agility, as well as to curb behavioral issues. He supports any organization that places canines with returning veterans and those suffering with disabilities, including Canine Companions for Independence, an organization that provides assistance dogs free of charge to recipients.

Leonard grew up in and around Boston, and anywhere else he has lived has paled in comparison to what this city offers!

Kate Jamieson

Insurance Manager

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Easy to talk to, task-oriented, and incredibly consistent, Kate has become an essential member of the Kiessling team in the three years that she has worked for the company.

Prior to arriving at Kiessling, Kate had worked in the fitness industry and she still enjoys an active lifestyle as well as keeping up with her three kids.

Kate grew up in Walpole, MA and still lives in the area.

Joshua Lizotte

South Shore Operations Manager

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Like many longtime Kiessling employees, Joshua worked his way up to his current role via many different experiences at the company. In 2004, Joshua started working for Kiessling as a mechanic, then transitioned to a role as a member of our office staff, and eventually became our South Shore Operations Manager.

Joshua enjoys sports and travel. He grew up in Central Massachusetts where he still resides.

Jon O’Connell

Vice President – Operations

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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.

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!

Jon Gutlon

GATRA-DAR Operations Manager

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As a high school student in the late 1970s, Jon took a summer job working with people who had special needs. Little did he know that the enjoyable experiences he was having that summer would eventually turn into a long-term career serving the needs of this unique population.

Jon joined the Kiessling team in 2008 and has since fulfilled a wide variety of important positions for the company, including managerial, administrative, and operational roles. Before becoming Kiessling’s GATRA-DAR Operations Manager, Jon was the company’s Assistant Operations Manager/Scheduler for Dial-a-Ride (DAR), Miles for Health and Franklin Area Bus (FAB) program, and the Tri Town Connector. In addition, he has been responsible for the Boston Human Service Transportation (HST) Program. Jon’s administrative and operational duties have spanned attendance keeping, billing, route development, driving, road supervision, dispatch, and more.

As GATRA-DAR Operations Manager, Jon has daily interactions with Kiessling customers and passengers and he is constantly putting his tremendous skills in customer service, scheduling, routing, and problem solving to good use.

Prior to his employment with Kiessling, Jon worked in service, parts, and sales for the Sony Corporation, for Lenbrook Industries, and for Service Bench, Inc.

Outside of running GATRA-DAR operations for Kiessling, Jon has a passion for music, including playing the drums. He is also an avid sports fan, and during football season, you will definitely find Jon watching his beloved Patriots. He also enjoys bike riding with his wife and doing yardwork, and treasures any time he has with his family. Through his church, Jon also reaches out to and offers aid to those less fortunate.

Jon grew up in Walpole and Sharon, MA and graduated from Sharon High School. While he and his family still reside in Massachusetts, he has moved to the coast so that he can enjoy more walks on the beach!

Jon Gutlon

GATRA-DAR Operations Manager

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As a high school student in the late 1970s, Jon took a summer job working with people who had special needs. Little did he know that the enjoyable experiences he was having that summer would eventually turn into a long-term career serving the needs of this unique population.

Jon joined the Kiessling team in 2008 and has since fulfilled a wide variety of important positions for the company, including managerial, administrative, and operational roles. Before becoming Kiessling’s GATRA-DAR Operations Manager, Jon was the company’s Assistant Operations Manager/Scheduler for Dial-a-Ride (DAR), Miles for Health and Franklin Area Bus (FAB) program, and the Tri Town Connector. In addition, he has been responsible for the Boston Human Service Transportation (HST) Program. Jon’s administrative and operational duties have spanned attendance keeping, billing, route development, driving, road supervision, dispatch, and more.

As GATRA-DAR Operations Manager, Jon has daily interactions with Kiessling customers and passengers and he is constantly putting his tremendous skills in customer service, scheduling, routing, and problem solving to good use.

Prior to his employment with Kiessling, Jon worked in service, parts, and sales for the Sony Corporation, for Lenbrook Industries, and for Service Bench, Inc.

Outside of running GATRA-DAR operations for Kiessling, Jon has a passion for music, including playing the drums. He is also an avid sports fan, and during football season, you will definitely find Jon watching his beloved Patriots. He also enjoys bike riding with his wife and doing yardwork, and treasures any time he has with his family. Through his church, Jon also reaches out to and offers aid to those less fortunate.

Jon grew up in Walpole and Sharon, MA and graduated from Sharon High School. While he and his family still reside in Massachusetts, he has moved to the coast so that he can enjoy more walks on the beach!

Jerry Romano

Maintenance Manager

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Jerry grew up in a family of mechanics and always remembers having a passion for cars and wanting to see what made them go. Personally and professionally, Jerry loves to talk about cars, cars, and more cars. In fact, when he’s not managing the maintenance of Kiessling’s fleet of vehicles and helping his mechanics fix any issues, you can find Jerry working on his own car.

Jerry has been a mechanic for 35 years, and started his career with Central Jeep Chrysler Dodge RAM of Norwood, MA. But he plans to make Kiessling Transit his last stop as a mechanic.

Jerry grew up in Boston, MA.

Courtney Damarell

Human Resource Manager

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In 2011, after completing an administrative training class, Courtney landed a clerical position at Kiessling, where she quickly stood out to management as being very detail-oriented, reliable, and motivated. Courtney’s skills, personality, and strong work ethic make her a perfect fit for our HR and Payroll department, where she now serves as Human Resource Manager.

When she’s not overseeing employee hiring and training, resolving payroll issues, or managing the company’s policies and regulations, Courtney enjoys the great outdoors, especially in the summer when you can find her by the pool or at the beach.

Courtney supports March for Babies, which funds lifesaving research, breakthroughs and programs for babies who are born too soon or with life-threatening complications. This is a very personal cause for Courtney because her own daughter was born prematurely.

Courtney grew up in Norton, MA and still lives there with her family.

Claire DiPillo

MWRTA Assistant General Manager

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Claire is a highly respected 40-year veteran of the transportation industry. Her very first experience in transit was with Kiessling in 1977, providing rides to special needs children. She so thoroughly enjoyed her daily interactions with her passengers that she decided to dedicate herself to a career in disability transportation services. Despite the longevity of her transit management career, Claire has worked for just two transportation companies, one of them thankfully being Kiessling Transit.

Claire has held almost every position possible at Kiessling Transit over the 34 years that she has been employed here. There are probably very few employees at Kiessling that have as much overall knowledge and understanding of our operating system as Claire.

As MWRTA’s Assistant General Manager, Claire works side-by-side with Chuck Curran, the MWRTA General Manager, to oversee and manage drivers, dispatch, and all daily operations. Prior to her appointment to this key management position, Claire was Kiessling’s General Manager of MBTA THE RIDE operations and Driver Manager for our joint venture with National Express. She has also been a Kiessling driver, scheduler, and dispatcher.

Claire loves spending her weekends with her family, watching sports, and taking the occasional trip to the casino. Like many Kiessling employees, Claire is a Massachusetts native having grown up in Roxbury, MA.

Chuck Curran

MWRTA General Manager

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When Chuck was 18 years old, he went to work with his brother-in-law who was a driver for MBTA’s THE RIDE. That was it for Chuck; he’d found his true passion was for transportation and set out on a lifelong career path in the transit industry. Chuck has had an extremely successful 35-year career in the industry, the last 15 of which have been with Kiessling Transit, where he currently serves as the MWRTA Demand Response General Manager.

Chuck has a comprehensive understanding of both fixed route and demand response transit systems as a result of holding a variety of positions at Kiessling as well as having a wide range of jobs in the transportation industry at large. At Kiessling, he has been an operations manager, driver, scheduler, and dispatcher. In addition, Chuck has previously had responsibility for making sure drivers are equipped properly and on-time at morning pull-out; assuring vehicle readiness and improving on-time performance by coordinating with maintenance, dispatch, and scheduling personnel; and managing the DDS and SPED services for multiple brokers, including GATRA and MART.

Prior to working for Kiessling, Chuck’s transit system experience was already quite broad as he had served as a scheduler and driver with MBTA’s THE RIDE, an Operations Manager and Sales Representative with Central Transport and Watkins Motor Lines Trucking, and a dispatcher with the Greater Lynn Senior Services (GLSS).

What has made him so successful at Kiessling and, specifically, in his role as the MWRTA’s General Manager is his knack for considering all sides and possibilities when managing people and dealing with problems.

As part of the senior leadership team at Kiessling Transit, Chuck never loses focus on what is the number one priority for the company – to provide customers and passengers with the highest level of service and respect, and therefore, satisfaction.

While Chuck is enamored with the transportation industry, he also has time for a lot of other interests, including travel, Sudoku puzzles, watching sports, eating ice cream, and, most especially, being with his grandkids. Chuck grew up in Dorchester, attended Don Bosco Technical High School in South Boston, and served in the U.S. Army as a medic from 1981 to 1984.

Bob Tobin

MWRTA Safety Manager

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Over 18 years ago, Bob chose to pursue a career with Kiessling because he loved working with people and had a desire to specifically serve the special needs population. He spent his first four years at Kiessling driving and as a dispatcher before being promoted to Kiessling’s Safety Manager. In this supervisory role, Bob took the initiative to establish a workplace safety system that addressed training, prevention, mitigation, and emergency responses and has become an industry benchmark.

Bob also served as Safety Manager of the MBTA’s South Shore Service Area of THE RIDE for seven years. He was instrumental in ensuring the success of this operation as he was responsible for developing and implementing all employee training programs. In his tenure with THE RIDE contract, Bob trained over 350 personnel, oversaw customer service, and was responsible for compiling training and National Transportation Data reports for the MBTA.

Now, as MWRTA Safety Manager, Bob leads weekly operator training sessions, including the National Safety Council’s Defensive Driving Course #4, First Aid/CPR, and Automatic External Defibrillator training. He also trains drivers in Passenger Assistance and Sensitivity and constantly keeps drivers appraised of the latest safety information. In addition, Bob conducts interviews and requests CORI and national background checks on prospective employees, as well as road tests and evaluates MWRTA trainees.

Bob has received extensive safety training and earned a variety of certifications, himself, in order to better teach others. He is Train-the-Trainer Certified under the National Safety Council, Instructor Certified in CPR/First Aid, Defensive Driving, and Passenger Assistance/Sensitivity from the University of Wisconsin, and an NHTSA-certified Technician for Seat Belt and Child Restraint Systems.

Bob attended the Community College of the Air Force , Maxwell AFB, AL and earned many medals and commendations for his service in the military. Many of the accolades Bob received are in recognition of his outstanding character. He is the type of person who would give you his last dollar and the shirt off his own back; whether it’s family, friends, coworkers, customers, or clients, Bob is always willing to do anything he can to take care of others.

Bob is very humble when it comes to talking about himself, but when it comes to his children, he loves to brag about their accomplishments. He also follows the local sports scene, especially the New England Patriots. On the weekends, if he’s not watching sports, you can find Bob doing yardwork, helping out a family member, barbecuing or spending the day out on his boat. In addition, around the holidays, Bob takes special interest in volunteering and supports Toys For Tots as well as many other organizations that serve the less fortunate.

Bob grew up in and around Boston and the South Shore, MA.

Ana Havey

Finance Controller

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In 2007, Ana was invited to join the finance department at Kiessling Transit by the controller at that time. From the start of her career at the company, Ana demonstrated a strong work ethic, an unmatched attention to detail, and excellent project management skills. That’s why, when the controller who hired her moved on, Ana was the clear choice to be promoted to the role of our top Finance Controller.

With two decades of experience in finance under her belt, Ana is an expert in financial analysis, financial reporting, compliance auditing, process and cost optimization, and risk mitigation. As Kiessling’s Finance Controller, Ana always has her pulse on the company’s finances and, over the past ten years, has implemented many innovative business solutions to improve performance of her department. While finance can be a very complex area of any company, Ana is well-versed at analyzing complicated situations and simplifying them into usable formats that our entire leadership team can understand.

Born in Portugal, Ana and her family came to the U.S. in 1981 for better opportunities, and she has shown a strong drive for success ever since. After graduating from the University of Massachusetts (Dartmouth) with a Bachelor’s Degree in Accounting, Ana worked for Quality Connections in Foxboro in multiple roles including Office Manager, Tech Support and Full Charge Bookkeeper. Just prior to coming to Kiessling, she was working as an Accountant/Controller and Transportation Coordinator for State Line Scrap Company in Attleboro. Ana also holds an Associate of Business degree from Bristol Community College.

Her favorite activities outside of work are spending time with her family, cooking, knitting, reading and gardening as well as volunteering at school events and as a Cub Scout Den Leader.

Lars Kiessling

Chief Executive Officer

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Lars grew up alongside the growth of his parents’ transportation company and, as early as high school, was already contributing to the family business. However, Lars worked his way up the ladder at Kiessling Transit just like every other employee has had to, starting in part-time roles at first, such as janitor, monitor, driver, and maintenance inspection team line member.

After attending Babson College and focusing on Business Management and Entrepreneurial Studies, Lars joined Kiessling as a full-time employee in 1994. His responsibilities grew to managing business development, contract negotiations, controller, and personnel management and he was charged with taking the company to the next level of efficiency and payroll control, much of which he accomplished through innovation and technology.

For the last fifteen years, Lars has managed transportation routing and cost controls and has been responsible for interviewing, hiring and reviewing Kiessling’s all-important team of drivers. In addition, Lars has been responsible for office staffing and training and handles the bulk of contract negotiations on the company’s behalf. Lars was Kiessling’s Chief Financial Officer for several years before moving into his current position as Chief Executive Officer.

The communities that Kiessling serves are much more than just places of business for Lars and his family. He grew up in Walpole and the surrounding Massachusetts towns, and still lives in the area, so Kiessling customers and passengers are truly his friends and neighbors. That is why it is even more important to him that the company remains committed to having a family atmosphere, to treating all people with great respect, and to always displaying integrity in all business interactions.