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Director of Outdoor Experience

Boston, MA, USA | The Trustees of Reservations

  • Industry:
    Hospitality, Travel, & Leisure
  • Position Type:
  • Functions:
    General Management
  • Experience:
    3-5 years
Job Description:
66 people have viewed this job


The Opportunity. The Trustees is seeking an outdoor adventure and play expert who can mobilize people around an idea, build new strategies, and who can oversee a project from beginning to end. The Director will leverage both our powerful engagement platform and our network of spectacular natural places to provide innovative and immersive hands-on experiences which invite families and other visitors to go outdoors and to play. The Director is part of the Stakeholder Engagement Division, and reports to the Chief of Marketing and Engagement. The Trustees are seeking a dynamic leader and strategist to ensure the organization’s goals to “invite the next generation outdoors” are met as they are defined in the current strategic plan, Momentum. This strategy focuses on three areas:


Inviting families to play outdoors: This position will lead a process to conceive, design and build adventure play opportunities on both one signature Trustees site and at a smaller scale on 10-12 other sites. Each of these architectural interventions should be inviting for families to play and to serve as a way to introduce new families to the outdoors while also providing sustainable revenue.


Inviting new and non-traditional audiences outdoors: The director will partner with organizational partners to build strategies and initiatives which attract underserved or unengaged audiences or those audiences who have felt less comfortable or welcomed at natural and recreational places.


Curating new recreational experiences: The director will conceive and expand both guided and self-guided experiences across the organization’s recreational reservations. These activities may range from guided hikes to more adventurous outdoor adventures. All designed with audience interests and affinity in mind while also generating revenue to support efforts.


The Impact. We know that the values and experiences that we have as young people influence the rest of our lives. Connecting with the next generation, inviting them to our properties and developing a passion for conservation and nature is top organizational priority as highlighted in our 2023 strategic plan Momentum. We believe that the education of the natural world and learning how to become a responsible steward of the environment is a crucial development opportunity for our youngest constituents.


Are you a match? We are seeking highly motivated, energetic individuals who possess deep expertise and commitment to outdoor learning and play. Competitive candidates must have at least 4 years of experience working with and relating to children families as well as 4 years of experience in education, recreation, environmental or outdoor education, challenge course facilitation or camp leadership.


In This Role You Will.

I. Plan, develop and implement comprehensive outdoor adventure experiences that offer immersive learning and play experiences for kids and families and through which participants will develop a passion for conservation and nature.

Develop annual goals with appropriate evaluation and assessment metrics to demonstrate progress.

Design, implement and analyze program evaluations.

Increase the participation and diversification of outdoor recreation programs and participants.

Improve the quality and consistency of current program offerings.

Develop customized programming solutions to meets the needs and goals of specific properties.

Partner with the Volunteer Management Team to leverage the skills and resources of Trustees volunteers to support and operate some programming.


II. Train and empower staff to facilitate, teach and lead outdoor programs that are exciting and enriching, while giving students an understanding of the beauty and diversity of our planet:

Build teaching and facilitation capacity for program staff through year-round training and facilitation workshops.

Teach instructors (Trustees staff and volunteers) how to make lesson plans and maintain curriculum resources through ongoing staff training workshops.

Mentor, motivate, and inspire property staff.

Supervise and maintain high standards of health and safety, and train staff to follow Risk Management policies in all activities.

Provide professional development opportunities and activity enrichment ideas for property staff.


III. Create a network of adventure interventions: Playscapes and adventure installations have been successfully implemented at several Trustees properties and are proven to welcome kids to relax and play in nature in a way that feels safe and inviting for parents and grandparents. The Director will conceive and design architectural interventions that will fit the landscape and beckon the next generation to experience the outdoor world in ways that are comfortable for them.


IV. Strengthen diversity, equity, and inclusion across all programs: The Trustees seek to serve all families and communities in the Commonwealth. The Director will drive strong collaboration internally and externally to engage with and mobilize underrepresented communities. The Director will establish and manage community partner networks (CBO’s, churches, local government bodies), undertake program market analyses to understand what programming specific communities are seeking, and will also develop effective methods for mobilizing attendance. Additionally, the Director will oversee events and key engagements with underrepresented communities and their stakeholders.


V. Collaborate with Marketing and Engagement colleagues to create and share an Outdoor Experience brand: The Director will develop and implement robust marketing of Outdoor Experience offerings including, but not limited to social media, print collateral and web pages.


Main areas of focus.

60% Program Management: project managing new adventure play installations, measuring program effectiveness.

15% Lesson planning and curriculum development.

15% Capacity building and training staff.

10% Recruiting diverse audiences.

Other Information

Qualifications & Experience:

Bachelor's degree. Master's degree in a related field (Outdoor Education, Recreation, Parks/Tourism, etc.) preferred.

The successful candidate will have a minimum of 4 years of full-time professional experience as a supervisor of an outdoor recreation/wellness/education industry and will also have 4 years of experience working with children and families.

Must have experience designing and managing outdoor programs, outdoor pre-orientation programs, and/or outdoor education programs such as summer camps, Outward Bound or NOLS.

You must be safety-oriented. Certifications in Wilderness First Aid and CPR are a plus.

Must have prior experience developing and managing departmental budgets.

Proven track record of success in developing and managing productive partner relationships.

Availability and flexibility to work weekday evenings and weekends as needed, as well as travel to statewide properties and partner organizations.


Highly analytical, data-driven decision-maker and organized problem solver; with consistent attention to detail.

Self-starter with an ambitious spirit, willing to multi task resourcefully and work independently.

Demonstrated strong business judgement with the ability to identify, prioritize, and articulate highest impact initiatives.

Unwavering commitment to quality programs and customer service.

Ability to quickly move from strategy to implementation and deliver programmatic results; having a demonstrated ability to take a hands-on approach.

Excellence in organizational and project management to achieve programmatic objectives.

Awareness, understanding, and appreciation of what it takes to build a diverse, equitable, and inclusive team

Ability to perform in a fast paced, dynamic and results oriented environment.

Track record of prioritizing workload to manage multiple projects with strict deadlines.

Strong communication, critical-thinking, and presentation skills; including the ability to provide written and verbal direction effectively.

Excellent relationship building skills with an ability to collaborate, negotiate, and work with a variety of internal and external stakeholders.

Strategic thinker who is self-motivated and detail oriented, and who is equally comfortable developing a strategic direction and executing against that strategy.

Awareness, understanding, and appreciation of what it takes to build a diverse, equitable, and inclusive team.

Ability to handle a variety of constituencies and thrive in a complex environment with multiple priorities and make challenging and important decisions.

Entrepreneurial team player with a positive attitude and a commitment to collaboration.

Strong written and verbal communications skills, with the ability to explain concepts clearly and compellingly.

Passion for the values, mission and purpose of The Trustees.

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