Executive Director, Portland Trails

Direct Hire
  • Type: Direct Hire
  • Job #18518

We are very pleased to be partnering with Portland Trails in their search for an Executive Director.  

About Portland Trails

At Portland Trails, we engage people to help transform our community into a more walkable, bikeable, sustainable, and equitable place for all. We build and maintain trails that create important connections between neighborhoods. We nurture greenspaces and trails that support native plants and animals. We connect community members with each other and with nature. As a well-established, 31-year-old nonprofit urban land trust, our 76 mile trail network reaches within a half-mile of every resident in Greater Portland, and hosts over a million visits each year.


At this exciting moment in our organization’s existence, the Board of Trustees seeks a new Executive Director to lead our increasingly dynamic organization, team, membership, and community into its next generation of live, work, and play across Greater Portland. Might we be looking for you?


We believe that simply providing access to trails and greenspaces is not enough. People need to feel a sense of safety and belonging to comfortably and habitually use trails and outdoor spaces. To better understand the lived experiences of historically less likely trail users, we’ve been broadening our partnerships and building relationships across our service area with organizations and residents who engage and hold different identities than those we’ve reached in the past. These valuable perspectives– about trails, local greenspaces, placemaking, and what’s needed in their neighborhood to promote more positive health outcomes– are increasingly informing our considerations and priorities.


This work, breathing life into our deepening commitment to ensuring greater diversity, equity, inclusion, and belonging on and off the trails in Greater Portland, is emergent and evolving. The Portland Trails Board of Trustees is poised to move our organization to the next phase in its evolution: growing the impact of our work in the community; supporting our team of six in taking our next steps with intention; and doing so while guided by mission, vision, values, and strategy that are both ambitious and humble. 


About the Position 

The Executive Director provides staff leadership of the Portland Trails organization. The Executive Director leads and directs the organization’s efforts to fulfill its mission. The Executive Director is responsible for administration, program management, staff supervision and strategic planning for Portland Trails. 

Reports to

The Board of Trustees


  • Organizational Management and Leadership: Responsible for identifying opportunities for expansion of the Portland Trails network; working with key stakeholders and legal counsel to enter into easements and land purchase agreements; assuring maintenance and stewardship of trail network, Portland trails assets including offices, materials, vehicles, and supplies; and managing  ongoing community relationships. Responsible for managing IT systems and security with support of IT consultants. Serves as spokesperson for Portland Trails.

  • Financial Management: Responsible for financial management including budgeting, reporting, compliance, and working with bookkeeper and accountants.

  • Revenue and Donor Cultivation/Stewardship:

    • Identify and cultivate funder relationships, including donors and business partners,  and program opportunities in collaboration with the Director of Development.

    • Develop and implement strategies to increase and diversify funding and ensure organizational sustainability.

  • Grant Management: Responsible for fundraising and grant writing activities.

  • Staff Management: 

    • Manages and supervises staff including hiring, on-boarding, coaching, evaluating and off-boarding, as well as benefits, recruitment, retention, training, and professional development.

    • Develops and implements annual work plans, promotes collaboration among team members, and provides related progress reports.

  • Board Relations: 

    • Provides support and guidance to the Board on organizational governance including review of by-laws, membership activity, and corporate responsibilities.

    • Provides or manages support to Board Committees and other Portland Trails groups.

  • Strategic Planning:

    • Researches, studies, and integrates promising approaches for creating and maintaining trails, green spaces, community connections, partnerships, and active, healthy living.

    • Responsible for short- and long- term plans for the creation, preservation, and maintenance of trails in greater Portland.

  • Community Engagement: Develops and maintains a variety of community relationships and interactions with the organization by::

    • Promoting Portland Trails activity, influence, and impact across the community.

    • Hosting community engagement opportunities and events including the annual membership meeting.

    • Managing Portland Trails involvement in community,  transportation, and conservation planning with an emphasis on people-powered movement.

    • Representing Portland Trails in meetings with state, municipal, nonprofit, and community groups.

    • Managing communications and social media activity.

  • DEI Leadership: Leads the development of an organizational, working, and operating culture which fully integrates the value of diversity, equity, inclusion, and belonging.


Experience & Qualifications

  • Three-plus years of non-profit management experience

  • Demonstrated success in financial management

  • Strong organizational skills, including ability to prioritize and manage multiple projects, manage staff teams, and delegate when appropriate

  • Experience with fundraising, grant writing, grants management, and donor cultivation

  • Seasoned people manager with excellent social-emotional, intercultural communication, and racial equity competencies 

  • Ability to work effectively and collaboratively on a team with individuals from diverse backgrounds

  • Thrives in multicultural work environments

  • Ability to switch efficiently among different cultural frames of reference and communication modes

  • Excellent oral and written communication skills including public speaking and media relations

  • Experience convening stakeholders, considering multiple perspectives, and facilitating agreement, including community events, engagement, and partnerships 

  • Familiarity with relevant technology, including cloud-based collaboration tools such as Office365/G-Suite and CRM systems such as Salesforce, as well as social media competency

  • Experience working in outdoor recreation, land trusts, and/or trails environments


The starting salary range for this position is $85,000 – 95,000, commensurate with experience. In addition to a generous paid time off policy, benefits include a health insurance stipend, a retirement plan with employer match, and a flexible work schedule.


Please submit a cover letter and resume to Mary@prosearchmaine.com. Applications will be evaluated on a rolling basis. Applications received by April 15th will be ensured full consideration. If your experience looks a little different from what we’ve identified, and you think you’d be great in this role, please tell us more in your cover letter. 

Portland Trails is an equal-opportunity employer, committed to maintaining and growing a diverse team, and an anti-racist organization committed to doing business in keeping with core values of diversity, equity, inclusion, and belonging.

Apply to: Executive Director, Portland Trails

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ProSearch is Maine’s premier staffing and recruiting firm. Our job is to connect great people with great opportunities. Established in 1994, ProSearch helps Maine’s top employers build their teams by recruiting just the right people – from temp/temp-to-hire, to IT consulting, to direct hire- for just the right positions.

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