Outdoor Program Director (Full-Time)

Position: Faculty

Department: Upper School - Outdoor Program

Location: Milton Academy Campus, Milton, MA

Hours: Full-time with the flexibility to work nights and weekends

FLSA: Exempt

Classification: Faculty (Academic Year)

Milton Academy is an independent college preparatory K–12 school, boarding and day in grades 9–12, located just outside of Boston.

Milton Academy cultivates in our students a passion for learning and a respect for others. Milton students grow by developing their own identities, learning from and listening to the lived experiences of others, and living and working among peers whose differences they accept with respect and care.

In our ongoing work to create an environment that confronts bias, injustice, and bigotry, we encourage each other to be open to learning, explore our histories and identities, and seek to understand the world around us with a critical lens. At Milton, we prepare students to partner with their future communities to create a more just world, and to have the courage to speak up and live by our motto, “Dare to be true.”

Summary of Position:

Milton Academy seeks a Director for the H. Adams ‘32 Carter Outdoor Program beginning in the fall of the 2025-26 academic year. This is a full time position and may include campus housing. The Director job is about ¾ of the workload of a full time position and therefore will ideally be combined with classroom teaching or other equivalent responsibilities. Part-time candidates may be considered but full time applicants will have priority.

Program Overview:
Founded in 1947 by mountaineer and skier Ad Carter, a Milton alum and later a teacher of modern languages at Milton Academy, the Program teaches rock/ice climbing, hiking/backpacking, sea kayaking and canoeing, and other outdoor skills in both an after-school program and through weekend and school break outings.

Students may elect into the after-school program in any of the three traditional sports seasons in fulfillment of their athletics requirement. The after school program offers outdoor rock climbing and hiking in the fall and spring, and indoor climbing in the winter. In the past, the program has offered sea kayaking in the fall and spring as an option as well.

The after school program offers weekend day, and occasional overnight, trips most weekends of the school year. The number and length of trips varies from month to month depending on the school schedule. We travel weekly to destinations as close as the Blue Hills (5 minutes away) and as far away as the White Mountain National Forest in New Hampshire. Most weekend trips are led by our in-house and adjunct instructors with occasional contract help from local guide services.

The program also takes advantage of spring and, ideally, in the future, summer breaks to run week-long trips that expose students to more in-depth experiences. In the past these trips have been domestic (Yosemite, Zion, Joshua Tree) and international (Belize, Baja, Bahamas, Costa Rica).

Position Overview:

The Director serves as a member of the teaching faculty of the Academy and oversees all aspects of the Program as outlined above and in the Essential Functions and Responsibilities and Competencies section below.

The ideal candidate will be a certified AMGA Single Pitch Instructor (or higher) and/or hold an ACA paddling certification and hold a WFA or WFR certification. The candidate will have previous experience leading wilderness trips, ideally with youth groups, have a wide range of outdoor skills, enjoy working with teenagers, and have a good sense of humor. We seek individuals who are flexible and are enthusiastic about working in a complex, academically rigorous boarding school.

We recognize that many applicants may not have the entire outdoor skill set outlined above or the combination of academic teaching and outdoor education experience. We seek either an individual who is well rounded in the outdoors OR an individual who has a high level of expertise in one area (climbing or paddling, for example) and the knowledge base to partner with adjuncts or contract guides for areas in which the individual has less expertise. Above all we seek a person who is passionate about the outdoors and about sharing that passion with students.

We DO want this position to also involve other campus involvement, ideally classroom teaching; the core of Milton Academy is our academic program and we therefore want all faculty to be grounded in the classroom experience of our students and faculty. Past directors have taught math, computer science, and natural sciences.

This position, in lieu of teaching responsibilities, could also be combined with other part time work in various advertised staff positions (Facilities, Development, etc. - see Milton Academy Careers website .

Essential Functions and Responsibilities:

H. Adams Carter Outdoor Program

• Outdoor leadership/instruction

  • Instruct two of the three afternoon programs

  • Lead or assist 2-3 weekend day trips a month

  • Work with the student leaders on the Outdoor Program Board

  • Organize and lead/chaperone week-long spring break trip

• Manage all weekend trip and after school logistics

  • Hire adjunct instructors

  • Book school vans

  • Make in person and online trip announcements

  • Manage weekend trip and afterschool program sign-ups

  • Communicate with signed up students

  • Conduct pre-trip meetings and outfit signed up students with gear and clothing

  • Make guide/instruction reservations and payments

  • Check student waivers and health forms with Office of Student Life and Health Center

• Manage and oversee program budget

  • Purchasing

  • Monthly credit card statement/receipts reconciliation

  • Budget planning and management

• Oversee all Program risk management

  • Formalize and maintain a risk management plan

  • Ensure leaders are practicing sound risk management in the field

  • Maintain relevant certifications

• Oversee and run school climbing wall

  • Maintain annual license with the Commonwealth of Massachusetts

  • Ensure proper use of the wall by other parties (middle school and PE)

• Manage Program equipment

  • Maintain and organize all equipment storage spaces

  • Maintain all Program equipment in good working order

  • Create and manage an equipment replacement program

  • Manage the check out and check in off all equipment

  • Purchase new equipment

  • Work with facilities department to maintain van and trailers

• Supervise faculty and adjunct instructors for the afternoon programs and weekend trips

  • Manage 2-3 faculty

  • Manage 2-3 non-Milton adjuncts

  • Organize periodic staff trainings

  • Maintain strong relationships with staff

Teaching and Curriculum

• Teach 1-2 sections of an academic subject (science, math, computer science, art, history, etc) or equivalent responsibilities

• Participate in department meetings (if applicable)

• Participate in a course group team (if applicable)

Advising

• Serve as an advisor to a group of up to seven students, engaging in advisor meetings each week.

• Connect, support, communicate, encourage, and celebrate each advisee

  • Facilitate students' social-emotional learning and growth in alignment with all school programming through small group meetings.

  • Build deep relationships with each advisee and assist them in navigating challenges they may encounter.

  • Form relationships with and act as a liaison between the school and advisee families; serve as the first point of contact between the school and families.

• Read and be familiar with all relevant materials, most importantly the Student Handbook and the sections of the US Faculty Handbook on academic regulations and diploma requirements.

• Be informed about course offerings for the following year and help each advisee select programs that are challenging and appropriate, as well as areas of special interest.

• Review each advisee’s grades and comments.

• Craft formal advisor reports for each advisee two times per year, offering overarching perspectives on their progress, and acknowledging a broader view of their academic and community achievements at Milton.

• Should an advisee need additional support in a particular area, be in steady contact with the advisee’s teachers, administrators, and/or other committees as needed.

• Attend all upper school student required weekly assemblies, programming, and special events (e.g., community service day, pep rallies).

• Attend class trips, retreats, and social events arranged by the director of student activities or the class dean.

Community

• Be a visible, accessible presence around campus.

• Contribute to creating a positive community culture that ensures students are heard, seen, valued, and cared for.

• Share in the enforcement of our expectations for students.

• Actively participate in greater community enrichment activities, such as advising a student activity, acting as a faculty sponsor to a student club, coaching an athletic team, leading an intramural sport or acting as an affinity group advisor.

• Complete all chaperone and/or supervisory duty, as assigned; lead and facilitate weekend programming / activities and supervise recreational activities both on and off campus.

Residential Life (if residing in on-campus housing)

• Act as a mentor and role model in all areas of the residential program, demonstrating a commitment to the success of each student, especially in the areas of social and emotional development.

• Contribute to creating a positive community culture within the residential life program that ensures students are heard, seen, valued, and cared for.

Other Professional Expectations and Responsibilities

• Work cooperatively with students, parents, peers, administration, and community members.

• Act in a manner that is respectful, generous toward others, supportive of colleagues, and based in a belief in the competence and good intentions of all members of the community.

• Communicate openly and promptly, supporting colleagues, students, and the integrity of the institution in conversations with students and parents.

• Create and maintain classroom and campus environments that are open and flexible, reflecting the school’s values related to diversity, equity, and belonging.

• Strive to grow and improve professionally, demonstrating a commitment to continuing professional development in alignment with the upper school’s growth statements.

• Exhibit skills in collaborative problem-solving, critical thinking, and teamwork.

• Meet deadlines.

• Attend all school-wide, divisional, and faculty meetings and events and serve on committees as required.

• Prepare for and participate in opening of school programming, family visit days, graduation, and all other key student/family moments that are part of the school calendar.

• Complete school-required training.

• Abide by the school’s policies and procedures as outlined in the provided handbooks.

• Communicate with the appropriate supervisor when unable to meet any professional obligation.

Supervision to be received: Supervised by the US Principal and Dean of Faculty

Supervision to be exercised: 2-3 faculty instructors and 2-3 adjunct instructors

Education/Certification/Licensure

Required: A bachelor’s degree

Preferred: A master’s degree. AMGA, ACA, wilderness first aid certifications.

Experience

Required: A minimum of three years of proven experience teaching and creating curriculum either in schools or in an outdoor setting.

Preferred: Experience working in an independent boarding / day school

Competencies

Required:

• Expertise and/or proficiency in a range of outdoor skills.

• Expertise and/or working knowledge of rock and ice climbing, sea-kayaking, hiking, camping, winter hiking, outdoor cooking, backcountry skiing, cross country skiing, and other outdoor equipment.

• Excellent verbal and written communication skills.

• Demonstrated computer expertise, including proficiency in Google Workspace.

• Ability to work collaboratively with internal and external constituencies.

• Understanding of confidentiality and related issues.

• Receptive to supervision and professional development.

• Desire to be a part of a dynamic educational community.

Physical Abilities

Required:

• Must be able to work at a computer for up to 8 hours each day in conjunction with OSHA requirements.

• Must be able to teach in a classroom setting and use relevant instructional technology.

• Must be able to move around the Milton Academy campus without restriction.

• Must be able to lift up to 40 pounds and move typical outdoor equipment easily: backpacks, canoes, sea-kayaks, ropes, etc.

• Must be able to, yourself, comfortably hike or backpack up to 10-12 miles a day in rugged terrain such as those found on the high peaks of the White Mountains of NH, rock climb, ice climb, sea kayak, canoe, camp overnight, and other outdoor activities, all while leading students.

• Must be able to drive an 11 passenger van of students, at times while towing a trailer.

All interested internal candidates must complete an application for promotion or transfer and inform your supervisor as soon as possible.

The essential functions and basic skills have been included in this job description; it is not intended to be construed as an exhaustive list of all functions, responsibilities, skills and abilities. Additional functions and requirements may be assigned by supervisors as deemed appropriate. This position description is subject to change at any time.

An equal opportunity employer, Milton embraces diversity and the pursuit of excellence. All qualified applicants will receive consideration for employment and will not be discriminated against on the basis of race (including natural and protective hairstyle), color, sex (including pregnancy and pregnancy related condition), sexual orientation, gender identity, gender expression, religion, religious creed, physical or mental disability, age, genetic information, veteran status, ancestry, citizenship, national or ethnic origin or any other status protected by applicable law.

NOTE: This is a cross-posted position. Only one will be hired.