Transition Facilitator

Posted Wednesday, August 19, 2026 at 4:00 AM Show your passion by empowering youth and families when joining the Wayside team! Wayside is one of Massachusetts' most respected youth and family-serving agencies, supporting more than 6,000 youth and families annually across Central, Eastern, and Northeastern regions. We invest in our employees' wellness with comprehensive benefits, including tuition and training reimbursement, a PTO package with 3 wellness days, 9 paid holidays, and up to 3 weeks of vacation in the first year. Enjoy a learning environment with free training, CEUs, and more, along with exceptional medical benefits, financial health supports, and career development opportunities. Salary: $21.00 - $26.50/hour depending on experience and degree + sign - on bonus (half paid after 6 months of employment and half paid after 1 year of employment/pro-rated for part-time). Wayside’s is seeking a dynamic and compassionate Case Manager/Transitional Facilitator to provide a variety of case management and related services to DCF young adults (18-22 year old) residing in transitional housing through the Waverley Oaks Transitional Housing Program. Looking for an experienced individual who has worked 1+ years within residential. Looking for folks who can be strong guides to young adults. What you will do: Coordinate intake assessments for new participants. Schedule weekly case management meetings with assigned participants. Develop, implement, and evaluate service/participation plans in collaboration with participants. Provide individual and group life skills assessment and education/training for participants. Provide employment assistance, career development, and apprentice job matching for identified participants. Develop, monitor, and evaluate apprenticeship experiences. Develop and maintain a broad network of community-based support services, including health, employment, education, counseling, self-help, community service, etc. Provide counseling, crisis intervention, referrals, service linkage, and advocacy on behalf of program participants. Provide an appropriate level of monitoring and supervision for program participants. Provide follow-up services for up to six months to interested former program participants. Complete all documentation as required. Participate in all weekly and required agency staff meetings, required agency trainings, supervision with the Program Director, and assigned meetings in the community. Assist with the development and implementation of appropriate policies and procedures. Ensure compliance with Wayside Youth and Family Support Network policies and procedures. Competencies/Traits of Our Superstars: Charismatic Empathic Dedication Reliability Teamwork MinimumRequirements: Bachelor's degree preferred, not required. Bilingual capacity is extremely preferred. Must haveat least 1 year of experience working with an adolescent or young adult population. Haveat least 1 year of experience working with residential or programs for people who have been homeless. Driving in the community is a requirement of this position; please ensure you have a valid driver's license and access to a reliable vehicle. We will train you in: Motivational Interviewing; Courageous Conversations; Attachment, Regulation and Competency Model (ARC); CPR and First Aid. #J-18808-Ljbffr Wayside Youth