Transition Facilitator

Overview

Posted Wednesday, January 7, 2026 at 5:00 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.

Apply today and earn a $2,000 sign-on bonus!

Salary: $21.00 - $26.50/hour depending on experience and degree + sign-on bonus (half paid after 30 days of employment and half paid after 90 days of employment; pro-rated for part-time).

Wayside’s is seeking dynamic and compassionate Case Manager/Transitional Facilitator to provide a variety of case management and related services to DCF and homeless young adults (18-24 year old) residing in transitional housing Program. Looking for an experienced individual who has worked 1+ years within residential or programs for people who have been homeless. Looking for folks who can be strong guides to young adults.

• 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 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 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.

Bi-lingual capacity extremely preferred.

MAP certified preferred, not required.

• Must have at least 1 year experience working with an adolescent or young adult population.
• Have at least 1 year 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.

Motivational Interviewing;
Courageous Conversations;
Attachment, Regulation and Competency Model (ARC); CPR and First Aid.