Transition Facilitator

Wayside Youth; Waltham, Northern (MA, KY); Hybrid; USD 29,000 - 37,000; Full time

Benefits offered by this job

Tuition reimbursement

Wellness PTO days

9 paid holidays

3 weeks vacation (first year)

Training & CEUs

Excellent medical benefits

Career development opportunities

Job summary

Wayside Youth seeks a dynamic and compassionate Case Manager/Transitional Facilitator to provide case management and related services to DCF young adults (18-22) in transitional housing through the Waverley Oaks program. Ideal candidates have 1+ year experience with adolescents/young adults and residential/homeless programs.

Responsibilities include intake coordination, weekly meetings, life skills training, employment assistance, and building a network of community supports.

Qualifications

• Bachelor's degree preferred, not required.
• Bilingual capacity is extremely preferred.
• Must have at least 1 year of experience working with an adolescent or young adult population.
• Have at 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.

Responsibilities

• 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.

Skills

Driving

Education

Bachelor's degree preferred

Job description

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.