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Deputy Director

The Squared Network
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Deputy Director 

Job Description


0. Organization Overview

The Middlesex Squared program is a three-summer, five-week college access program designed to prepare high achieving, first-gen and/or low-income high school scholars for college, with a strong focus on STEM courses, college counseling, community building, and extracurricular activities. 

Scholars live and learn at Middlesex School in Concord, MA where they participate in up to six hours of academic classes, followed by the Active Program in the afternoons. The program aims to foster scholars' intellectual, social, and emotional development, promoting independence and responsibility. 

 

I. Role Responsibilities

The Deputy Director serves as the Executive Director’s primary operational and administrative partner and functions as the program’s second-in-command during the summer. The Deputy Director supports program-wide planning and execution while taking direct responsibility for team coordination, operational oversight, staff leadership, and student experience.

This position is ideal for a strong people leader and systems thinker who can manage operations while also supervising and supporting staff in a fast-paced residential environment. The Deputy Director plays a critical leadership role in ensuring a safe, joyful, and academically rigorous program for students.

This position is full-time for the duration of the contract period, with remote responsibilities leading up to and following the summer program, and on-site responsibilities while the program is in session. The Deputy Director is required to live on campus for the duration of the summer program (room and board provided).

In this role, you will:

Program Leadership & Execution

  • Serve as a key leadership presence for staff and scholars, supporting overall program success
  • Coordinate cross-functional daily program execution across academics, student life, and operations
  • Lead planning and execution for high-leverage program moments, including orientation, arrival, family-facing events, and end-of-program ceremonies
  • Support continuous improvement through end-of-program debriefs, surveys, and documentation

Staff Leadership & People Management

  • Supervise and support key staff leaders (including operations and student-life roles, as applicable)
  • Provide coaching, support, feedback, and accountability to ensure staff performance and alignment with program expectations
  • Support staff onboarding, training, and culture-building; model professionalism, warmth, and high expectations
  • Serve as a point person for escalation and decision-making support when staffing challenges arise

Student Enrollment & Family Communication

  • Support student enrollment workflows including tracking required forms and documentation
  • Communicate with families regarding enrollment needs, student travel, and key program policies
  • Support student travel and arrival/departure logistics in coordination with other leaders

Residential Oversight, Wellness Support & Duty Rotation

  • Participate in the program’s leadership duty rotation, including serving as Admin on Duty 2-3 times per week as needed
  • Support evening supervision, study hall, and lights-out coverage as assigned
  • Provide student wellness/crisis support as needed, in alignment with program protocols and escalation procedures
  • Help ensure consistent enforcement of program norms and student safety expectations

Additional Responsibilities

  • Foster a collaborative, mission-aligned student and staff culture
  • Support weekly leadership meetings, coordination, and documentation
  • Additional duties and responsibilities as needed to ensure program success
  • Support and oversee the following key program events:
  • Weekly Events: 
    • Staff Meetings: Thursdays, 12:05 pm - 12:45 pm
    • All School Meeting: Tuesdays, 11:00 am - 11:45 am
  • Special Events: (Dates subject to change prior to summer start)
    • Staff Orientation: Wednesday, June 17th to Friday, June 19th
    • Student Arrival and Welcome Events: Monday, June 22nd
    • Team-building and Convocation: Tuesday, June 23rd
    • First Day of Classes: Wednesday, June 24th
    • First Week Evening Event: Friday, July 10th
    • College Visit Days: TBD
    • Coffeehouse: TBD (Evening)
    • Family Visit Day: TBD
    • Stepping-Up Ceremony: Friday, July 24th
    • Campus Wrap-up: Saturday, July 25th

II. Location and Duration

The Middlesex Squared program is conducted on the scenic Middlesex School campus, located in Concord, Massachusetts. The duration of the contract will be from May 26th, 2026 through July 31st, 2026. 

Deputy Director is required to be on campus at Middlesex School from Wednesday, June 17th, 2026, through Saturday, July 27th, 2026.
 

III. Benefits

  • Free room and board are provided during the program.
  • Teach and inspire diverse scholars, supporting their educational and emotional growth.
  • Experience the beauty of Concord, Massachusetts, with easy access to outdoor activities and Boston
  • Develop professionally by taking on additional responsibilities, engaging in workshops, and contributing to a growth-focused work culture.

IV. Qualifications

  • Bachelor’s degree or professional experience  in counseling, education, youth development, or related field required
  • At least 2 years of relevant professional experience preferred
  • Demonstrated experience supervising, coaching, or leading others strongly preferred
  • Strong communication, judgment, and interpersonal skills in student-facing environments
  • Ability to manage multiple priorities while maintaining professionalism, calm, and clarity
  • Commitment to educational equity and supporting first-generation and low-income students

V. Compensation

Our summer staffing model is designed to balance fair pay, role clarity, and long-term program sustainability. This position has a budgeted amount for the full program and reflects the scope and time commitment of the role as designed.

 

We strive to maintain consistency and equity across our team while keeping the program accessible to students and families.
 

This position is compensated at a flat rate of $10,000 for the full contract period, reflecting the operational responsibilities and time commitment of the role.