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Senior Counselor – Post High School

Job in Waltham, Middlesex County, Massachusetts, 02254, USA
Listing for: AdvancingMilestones
Full Time position
Listed on 2026-10-01
Job specializations:
  • Education / Teaching
Salary/Wage Range or Industry Benchmark: 61000 - 68000 USD Yearly USD 61000.00 68000.00 YEAR
Job Description & How to Apply Below

Milestones Day School and Transitions Program is a year-round private special education school (elementary, middle, high school, & post high school) located in Waltham, MA and works with students with autism spectrum disorders, learning disabilities, and a variety of attention and/or psychiatric challenges. We service students ranging in age from elementary grades through post high school, and our staff work in multi-disciplinary teams to support students in particular grade cohorts.

We are currently recruiting for a Senior Counselor/Teaching Assistant to join our Post High School team.

The Post-High School (PHS) Senior Counselor will:

  • Ensure the safety of PHS students while providing compassionate, therapeutic support during all program activities.
  • Lead a homeroom of 6-8 students during morning arrival and afternoon dismissal, ensuring students are safe, regulated, and previewed for the day.
  • Supervise PHS counselors (i.e., mentorship, in-the-moment training/modeling, complete annual evaluations, Tier 1 checklists, monthly supervision meetings).
  • Responsible for the onboarding, training, and supervision of counselors as assigned by your supervisor.
    • Including but not limited to: bi-weekly regular supervision check-ins with direct reports, providing coaching, providing feedback, being a go-to for questions, regular observations, mediating/problem solving concerns, completing annual and bi-annual performance evaluations for direct reports.
    • Maintain organized and up-to-date records of meetings and goals of direct reports.
    • Provide timely responses to the needs of direct reports.
    • Model professionalism and workplace expectations.
    • Active and ongoing partnership with the Program Managers and Human Resources regarding personnel matters (as needed).
    • Attend regular supervision and team meetings.
    • Practice professional discretion and sound judgment.
    • Providing guidance. Advise counselors; operate in an inquisitive way to determine the root cause of issues; recommend and execute appropriate plans to develop people, optimize the talents of team members, and encourage an engaged culture.
    • Address employee relations in a positive and proactive manner with exceptional judgment while also providing timely feedback.
  • Plan and teach a 50-minute elective course with 6-10 students 3-4 times per week.
  • Support PHS community-based instructional trips twice per week. This includes driving students to/from community locations and providing therapeutic, functional coaching which aligns with lesson objectives.
  • Aid PHS program managers, teachers, and clinicians in planning and leading weekly small-group community outings for a cohort of 4-5 students who are approaching their transition out of Milestones. The purpose of these outings is to strengthen work readiness skills.
  • Lead the collection and analysis of Massachusetts Work-Based Learning Plan data to ensure PHS maintains accurate, measurable information regarding students’ current work skills. This data informs progress notes, IEPs, and transition portfolios.
  • Obtain certification in “Medication Administration for Unlicensed Personnel” to administer student medications in community settings as needed (under guidance of school nurse).
  • Create and send PHS weekly newsletter to families every Friday afternoon.
  • Coordinate routine and emergency maintenance for PHS vehicles (e.g., schedule annual inspections, oil changes, replacing vehicles when lease terms end). This responsibility includes being the PHS program’s primary contact for Wellesley Toyota, where the vans are leased.

Qualifications:

  • Bachelor’s degree in a related field required;
    Master’s degree strongly preferred
  • Supervision and/or mentorship experience strongly preferred
  • A minimum of 3 years of experience in special education,…
Position Requirements
10+ Years work experience
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