Director of Philanthropy

Supervisor: Executive Director

Status: Fulltime, Permanent (40 hrs/wk)

Organization Overview

Portland Trails is a 501(c)(3) nonprofit organization based in Portland, Maine, dedicated to creating and maintaining a 100-mile network of trails that connect people with places and with one another.

For more than 35 years, Portland Trails has played a central role in shaping Greater Portland’s trail system, advancing active transportation, environmental stewardship, and equitable access to outdoor spaces. The trail network provides significant economic and community benefits to the region including 921 jobs, $42M in earnings, $113M in local sales, as well as $290M of enhanced property values, $1.2M of annual healthcare savings, and between $2-5M of reduced climate impacts.

Working in partnership with municipalities, community organizations, and regional stakeholders, Portland Trails develops and maintains multi-use trails that support recreation, commuting, and community well-being. Guided by its 2030 Impact Plan, the organization is entering an important period of growth as it builds toward a future capital campaign and expanded regional impact.

Portland Trails is committed to creating an inclusive work environment where unique perspectives and talents are valued and appreciated. Our guiding values are community, inclusion, collaboration and stewardship. We strongly support and welcome all underserved communities who have traditionally lacked access to trails.

Position Summary

Portland Trails seeks a seasoned and relationship-driven Director of Philanthropy to lead and grow its major and planned giving program at a pivotal moment in the organization’s evolution.

This is a senior, externally focused position centered on major gifts, planned giving, and donor strategy. It is intentionally designed to allow focus on high-value relationship building rather than operational or transactional fundraising functions. This is not an all remote position, and requires regular hours in our Portland, Maine office.

Principal Responsibilities and Duties

Major Gifts Leadership

• Build, manage, and grow a portfolio of major donors and high-capacity prospects
• Develop and execute individualized cultivation and solicitation strategies
• Personally solicit and close leadership-level gifts
• Partner closely with the Executive Director on top donor relationships

Planned Giving

• Develop and expand Portland Trails’ planned giving program
• Integrate legacy giving into major donor strategies
• Strengthen long-term and endowment-based philanthropic support

Donor Strategy & Portfolio Management

• Oversee strategy for donor engagement across all giving levels
• Ensure consistent and meaningful stewardship practices
• Guide segmentation and relationship management using Salesforce and wealth screening tools

Annual Fund Strategy Development (Not Execution)

• Set strategy and direction for the annual appeal
• Partner with staff to ensure strong donor messaging and follow-up
• Monitor performance and recommend improvements

Foundation Strategy & Stewardship

• Provide strategic oversight of foundation relationships
• Partner with contracted grant writer to align proposals with priorities
• Ensure timely and thoughtful stewardship of institutional funders

Campaign Participation

• Play a meaningful role in preparing for and supporting a future capital campaign
• Partner with campaign consultant and leadership on major gift strategy
• Support donor cultivation and solicitation for campaign success (This role will not serve as campaign manager)

Board & Leadership Partnership

• Work closely with the Executive Director, Board of Trustees, and Development Committee
• Support and guide Board members in donor engagement and fundraising efforts
• Help strengthen a culture of philanthropy across the organization

Required Knowledge and Skills

• Demonstrated success in securing major gifts ($25K–$100K+)
• Experience with planned giving programs
• Experience working in or closely with a capital campaign
• Strong relationship-building and communication skills
• Experience with wealth screening, donor research tools, Salesforce or similar donor management platform
• Ability to work effectively with senior leadership and Board members
• Strategic thinker with the ability to execute

Position Profile

This is a highly relational, externally focused role requiring confidence, initiative, and the ability to engage donors in meaningful and aspirational conversations.

The successful candidate will be someone with 7–10+ years of progressive nonprofit fundraising experience and the ability to sit across from a donor and confidently ask for a transformational gift.

Organizational Structure

The Director of Philanthropy will report to the Executive Director and work in close collaboration with the Communications and Operations staff.

Portland Trails is in a period of thoughtful transition as it aligns internal resources to support a more strategic, relationship-based approach to fundraising. Operational and administrative support functions—including database management, gift processing, and annual fund execution—will be structured to allow the Director of Philanthropy to focus on major gifts, planned giving, and donor engagement.

The Director will collaborate closely with senior staff across the organization and will provide strategic guidance to colleagues involved in communications, events, and donor engagement activities.

Salary and Benefits

Salary range: $90,000–$100,000, commensurate with experience.

Portland Trails offers a competitive benefits package with medical/dental/vision, 5% retirement contribution, and professional development opportunities.

We are committed to a diverse and equitable workplace and experience on the trail. We encourage individuals to apply who bring diverse and underrepresented perspectives to our work, value difference, and we aim to offer equal opportunity to everyone. We support underserved communities and are working to help promote the needs of immigrants, Wabanaki and others.

How to Apply

Send cover letter and resume to ***email_hidden*** by June 5, 2026.