Career Specialist

Job Description Description

Location:

Worcester Community Justice Support Center
Worcester County Sheriff’s Office
365 Main St
Worcester, MA 01608

DEPARTMENT

Community Justice Support Center

TITLE

Career Specialist

JOB SUMMARY

The Career Specialist plays a critical role in supporting individuals with current or past involvement in the criminal-legal system by connecting them with meaningful employment, job training/readiness, and vocational opportunities. This position focuses on building strong relationships with employers, training providers, and community partners to create inclusive pathways to employment for justice-impacted individuals.

The Career Specialist will assess client skills and interests, provide job readiness coaching, support applications, and interviews, and advocate for fair hiring practices. A key component of this role is to reduce stigma around criminal records by connecting with employers to promote second‑chance hiring. The Career Specialist collaborates closely with the counselors and coordinators, workforce development teams in the community, and reentry service providers to ensure holistic client‑centered support.

• Engage and assess clients to identify employment goals, strengths, and barriers by utilizing assessment tools
• Develop individualized employment or training plans tailored to each client’s needs
• Build and maintain partnerships with employers and training providers open to hiring or working with justice‑impacted individuals
• Provide job readiness support including resume development, interview preparation, and soft skills training
• Work with employers to create pathways for referrals
• Work with employers regarding job openings
• Track client progress and provide ongoing support post‑placement to ensure retention and success
• Maintain accurate and timely documentation of services and outcomes
• Provide Cognitive Behavioral Therapy groups within the center to clients
• Help clients prepare resumes and cover letters, including mock interviews
• Adhere to Sheriff’s Office policies and procedures
• Perform other duties as required

• The ability to communicate effectively with people in a direct, clear and professional manner.
• General knowledge about the purpose of a community safety facility; understanding of the goals and objectives of a community correction program and a general familiarity with the court systems.
• Ability to communicate respectfully and professionally with clients in an empathic way.
• Proven verbal and written communication skills.
• Experience working with the justice‑involved population with diverse backgrounds.
• Working knowledge of Google Suite, Microsoft Excel and Word.
• Some physical effort demanded when performing testing functions under typical office conditions in a correctional/office setting.
• Possess an active driver’s license and be able to drive/transport individuals using the WCSO van/car, if needed.
• Frequently required to sit, stand, talk and hear.
• Must be able to work some evenings and cover additional shifts as needed.

• Mission Advancement:
  Accepts and demonstrates the WCSO and CJSC’s values. Demonstrates a desire to serve others and fulfill community needs while working to support the development of a positive teamwork environment.
• Works effectively with people of different backgrounds, abilities, opinions, and perceptions. Builds rapport and relates well to others. Seeks first to understand the other person’s point of view and remains calm in challenging situations. Listens for understanding and meaning; speaks and writes effectively. Takes initiative to assist in developing others.
• Operational Effectiveness:
  Makes sound judgments, and transfers learning from one situation to another. Embraces new approaches and discovers ideas to create a better team experience. Establishes goals, clarifies tasks, plans work, and actively participates in meetings. Strives to meet or exceed goals and deliver a high‑value experience for members of the team.
• Personal Growth:
  Pursues self‑development that enhances job performance. Demonstrates an openness to change, and seeks…