The Trustees of Reservations

200 High St.
Boston, MA 02110

Date Posted:
August 06, 2018

Eastern Massachusetts



Director of Enterprise - Boston (year-round, full-time)


Key Responsibilities:

The Director of Enterprise is a new position that will be responsible to creating exciting new profitable enterprises on Trustee properties statewide as well as leveraging and improving existing activities to achieve greater performance and profitability. This role will be responsible for a broad range of potential business opportunities including, retail, food, merchandise, hospitality, event rentals, camping, special projects and private sector partnerships.

Candidates could come from a wide range of backgrounds and do not need to have non-profit experience to be successful. They would ideally have experience in launching new ideas and businesses, strong planning and financial analysis skills and a demonstrated management experience. They must be prepared to travel statewide and they will be expected to work collaboratively across many positions and departments within the organization and represent The Trustees externally. Experience within a large organization or a matrix management structure is helpful.

Enterprise in integral to the visitor experience. We have ambitious goals for increasing the number of people who enjoy Trustees properties. In addition to identifying and launching new enterprises the Director of Enterprise will be a central resource for the General Managers, a subject matter expert who can provide oversight and guidance to our growing network of enterprise ventures. The Director will create a best-in-class customer experience at Trustees retail sites by strengthening merchandise mix, store layout/design, staff training, and customer service. They will increase the profitability of retail sites by implementing policies, procedures and best practices that improve efficiencies and margins, and by identifying and evaluating potential new retail locations and channels (possibly including online and/or pop-up/mobile stores). The Director will also work closely with the brand/marketing team to conceive of and produce branded merchandise for sale around the state and online.

Enterprise at The Trustees properties ranges from campgrounds, shops and inns to more informal, opportunistic enterprise ventures. The Director of Enterprise must have the vision and flexibility to manage effectively within that range. He/she must have the strategic vision to see opportunity where others may not, and the tactical aptitude to operationalize that vision. It will require both strong analytical and business planning skills and a creative entrepreneurial mind. This is a tremendous opportunity for someone who wants to apply their retail expertise and creativity in a mission-driven setting that’s making a difference for Massachusetts residents and communities.

Essential Functions: 

  • Measure current performance and advise on all existing enterprise sites
  • Identify, plan and implement new enterprise opportunities
  • Increase annual enterprise revenues annually in line with 5-year strategic goals
  • Develop sound business and financial plans for existing and new enterprise
  • Work collaboratively with Regional VPs, GMs and central departments
  • Report at Strategic Enterprise Committee, E-Team and Board when required
  • Establish and implement strategies and best practices for shop design, merchandise mix, inventory management, pricing, and customer service, with the goal of improving the profitability of retail ventures.
  • Coordinate buying and manage supplier relationships.
  • Identify and pursue opportunities for licensed and/or branded merchandise.
  • Evaluate potential new retail sites and channels; direct/project manage all aspects of approved new launches.
  • Work with Finance to collect and report relevant sales data.
  • Work with senior leadership to secure Board Committee input to/support for enterprise planning and growth.

Minimum Requirements

Education & Experience:

  • At least seven years of management experience overseeing operations and development concept for a non-profit retail or business, preferably outdoor industry, or destination based institution such as a high-end museum or gift shop offering both food and merchandise.
  • Experience as a buyer a plus and with inventory control and management
  • Demonstrated track record of success in a start-up/entrepreneurial retail environment preferred.
  • Experience hiring, training and managing shop staff.
  • Knowledge of retail trends and business models.


  • Experienced staff manager with the demonstrated ability to attract, retain, and motivate a high-performing team and, when necessary, to hold staff accountable for subpar performance.
  • Strong customer focus; demonstrated commitment to and understanding of customer service.
  • Experienced, effective negotiator.
  • Strategic thinker who is self motivated and detail oriented, and who is equally comfortable developing a strategic direction and executing against that strategy.
  • Entrepreneurial team player with a positive attitude and a commitment to collaboration.
  • Strong project manager, preferably with experience launching and growing retail ventures from the ground up, in addition to managing established retail sites.
  • Strong written and verbal communications skills, with the ability to explain concepts clearly and compellingly.
  • Ability to multi-task and perform at a high level in a fast-paced, results-oriented environment.
  • Fluency with financial/accounting software, especially Excel; strong comfort level interpreting financial reports.

This position requires the use of one’s own car for travel around the state with mileage reimbursement. The position is based in Boston at 200 High Street.

About the Organization:

The Trustees is an organization with a fascinating past and an exciting future. Our places are open to all and we thrive by involving as many people as possible in what we do. Founded in 1891, by a group of visionary volunteers, we preserve, for public use and enjoyment, properties of exceptional scenic, historic, and ecological value in Massachusetts and work to protect special places across the state. We have helped protect more than 50,000 acres, including 25,000+ acres on more than 100 reservations that are all open to the public. We are a non-profit conservation organization funded and supported entirely by our visitors, supporters, volunteers, and more than 60,000 member households.

The Trustees annual operating budget is approximately $32 million. Approximately $11 million or roughly 34% of those revenues are derived from enterprise activities, such as rentals, food service, retail, hospitality, farm shares (CSA programs) and permits. As part of its new strategic plan, The Trustees is looking to expand the revenues from enterprise in order to reduce the organizational dependency on philanthropy and to build greater financial resilience into our business model.

In addition to being an Equal Opportunity Employer, the Trustees of Reservations aims to create a thriving, inclusive workplace that values each member of our team. We aspire to reflect and effectively serve the residents and communities of Massachusetts, who are at the core of our mission.

How To Apply:

Candidates should submit their resume, cover letter, and salary requirements online via The Trustees online application portal.

We kindly request that you do not call to inquire about the status of your application. Those candidates chosen for interviews will be contacted

Apply by:
September 30, 2018
About this Organization:
The Trustees of Reservations is one of Massachusetts’ largest non-profits and the nation’s first conservation and preservation organization. We preserve and protect places of natural, scenic and historic beauty and hold these “reservations” in “trust” for public use and enjoyment. Our passion is to improve the quality of life in the Commonwealth, using our properties and their many programs as a powerful and compelling platform to engage more residents and visitors in our mission-driven work. We believe in protecting the irreplaceable forever, for everyone.  Today, we care for 117 special reservations -- from beaches to farms, gardens and historic sites – within minutes of every resident. Funded and supported entirely by our nearly 2 million visitors and supporters, and more than 60,000 member households, we invite you to find your place.