Transition Facilitator
Listed on 2026-08-07
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Social Work
Youth Development, Human Services/ Social Work, Community Health, Career & Life Skills Coaching
Posted Monday, August 3, 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.
- Charismatic
- Empathic
- Dedication
- Reliability
- Teamwork
- 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.
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