For Immediate Release

January 10, 2024


Amanda Powers
2nd Street
(518) 928-9888
[email protected] 

Outgoing director Jason Cuyler to assume new role at Berkshire County Sheriff’s Office

Lindsay MaynardPITTSFIELD, MA — The 2nd Street Board of Directors has elected Sergeant Lindsay Maynard as its new executive director following the departure of Jason Cuyler, who recently announced he has taken a position as Assistant Deputy Superintendent of Community Engagement at the Berkshire County Sheriff’s Office. Maynard will assume her new role at 2nd Street on April 1, 2024.

“Jason’s leadership has been a key element in the extraordinary success of 2nd Street. His knowledge of our clients’ needs and available services, as well as his vast network and credibility in the community, assured a level of trust and confidence from those we serve and those who support us. We are happy to see him advance in his career,” said Mark Gold, president of the 2nd Street board of directors. “We look forward to working with Lindsay, who brings considerable skills and ability to lead 2nd Street into the next phase of its growth.”

Maynard, a native of Lanesborough, is currently a corrections caseworker/Women’s Re-entry and Aftercare for the Berkshire County Sheriff’s Office. She holds a bachelor’s degree in rehabilitation and disabilities studies with a minor in psychology, along with a master’s degree in clinical mental health counseling, from Springfield College. She is also a graduate of the Western Massachusetts County Correctional Officers Academy and is presently enrolled in the Graduate Certificate in Nonprofit Management program at Northeastern University.

Maynard has been “an integral part of 2nd Street since its inception,” Gold said, noting that the organization works closely with the Berkshire County Sheriff’s Office to place referrals, facilitate aftercare case management, create workshops and other events, and help maintain a seamless transition between incarceration and reentry into the community.

“Gratitude fuels my excitement as I step into the role of Executive Director of 2nd Street. I’m grateful for the trust of Sheriff Tom Bowler and the advocacy of Mark Gold, and I give special thanks to Jason Cuyler for his leadership and guidance,” Maynard said. “I am ready to carry forward the community 2nd Street has created.”

Jason Cuyler said his experience at 2nd Street will help drive him forward at his new position.

“Working collaboratively with fellow Berkshire County community agencies and the 2nd Street support staff has been an honor, and I eagerly anticipate the opportunity to sustain these partnerships in my new capacity with the Sheriff’s Office,” Cuyler said. “Providing services and support for formerly incarcerated clients has been a rewarding journey, and I look forward to continuing this vital work for the betterment of our community.”

Sheriff Thomas Bowler praised both Cuyler and Maynard for their accomplishments.

“I am extremely proud of the incredible work Jason Cuyler has done as executive director of 2nd Street. What started as a simple vision — to work collaboratively with community agencies to address the needs of the formerly incarcerated — resulted in the creation of something very special,” Bowler said.

“Jason proved to be the right fit at the right moment in time. The time has come, however, for Jason to take on an even bigger role within the Sheriff’s Office,” Bowler continued. “I could not think of a better person to assume his role than Sergeant Lindsay Maynard. Lindsay is extremely qualified and is respected by her clients and her peers. I am confident that she will continue what Jason has started with great success. Our community is blessed to have such talented individuals devote their lives to helping others in need.”

About 2nd Street

Second Street Second Chances, Inc., better known as 2nd Street, supports formerly incarcerated persons in Berkshire County and connects them with the tools, programs and support they need to successfully reenter their community. 2nd Street is committed to treating formerly incarcerated individuals with respect and encouragement; providing them with job readiness skills and access to employment opportunities; preparing them to become productive and contributing citizens; and educating and advocating for communities to embrace them as such. Services and referrals include medical and mental health resources, substance use disorder services, financial resources and literacy, transportation, family reunification, housing, job training and employment, and legal services. Visit 2nd Street at