Assistant Director of Philanthropy and Alumni Engagement

Build Lifelong Connections. Advance a Mission That Matters.

For more than 100 years, Chewonki has helped people develop a deeper connection to the natural world, to one another, and to themselves. Through programs that challenge, inspire, and educate, Chewonki's mission is to inspire transformative growth, teach appreciation and stewardship of the natural world, and challenge people to build thriving, sustainable communities throughout their lives.

Why Now?

Chewonki is entering an important chapter in its history. Over the past several years, the organization has completed a successful multi-year comprehensive campaign that raised more than $25 million in support of strategic priorities, campus improvements, endowment growth, financial aid, and long-term sustainability.

Building on that momentum, Chewonki is continuing to invest in innovation, accessibility, and program evolution to ensure its mission remains relevant and impactful for future generations. As the organization navigates this period of transformation, philanthropy and community engagement remain central to its success.

The Assistant Director of Philanthropy and Alumni Engagement will join a collaborative and experienced team at a time of significant opportunity, helping strengthen relationships with alumni, families, donors, and friends while advancing the philanthropic support that sustains Chewonki's future.

We Are Seeking…

We are seeking an Assistant Director of Philanthropy and Alumni Engagement to help strengthen the relationships that sustain Chewonki's mission.

This is a fundraising and engagement role for an experienced relationship builder who is ready to take ownership of Chewonki's Annual Fund, manage a portfolio of donors and prospects, and help deepen engagement among alumni, families, donors, and friends.

Working closely with the Director of Philanthropy and Alumni Engagement, the President, program leaders, volunteers, and trustees, the Assistant Director will help connect people to the experiences, values, and community that make Chewonki meaningful, while helping to generate the philanthropic support that sustains the organization for future generations.

The ideal candidate is equally comfortable meeting with a donor, writing an Annual Fund appeal, welcoming alumni back to campus, and crafting a social media post that celebrates the impact of the Chewonki community.

What You’ll Do

Lead Chewonki’s Annual Fund program.
Manage a portfolio of alumni, families, donors, and friends.
Cultivate, solicit, and steward annual and major gift prospects.
Plan and support alumni and donor engagement opportunities, including Homecoming, reunions, volunteer activities, and regional gatherings.
Create and coordinate donor, alumni, and Annual Fund communications across email, direct mail, social media, and digital platforms to support engagement, stewardship, and fundraising goals.
Partner with colleagues across the organization to strengthen constituent engagement and philanthropic support.

What Success Looks Like

In your first year, you will take leadership of Chewonki’s Annual Fund, build relationships with key alumni and donor constituencies, manage a portfolio of donors and prospects, support engagement activities including Homecoming and regional events, and help strengthen the culture of philanthropy that sustains Chewonki’s mission.

Who Will Thrive Here

The strongest candidates will bring demonstrated fundraising experience and a genuine interest in building long-term relationships with alumni, families, donors, and friends.

This role is ideal for someone who is ready to lead an Annual Fund program, manage a donor portfolio, and play an active role in cultivating, soliciting, and stewarding philanthropic support.

Experience creating compelling donor, alumni, or constituent communications across multiple channels.
Confidence managing donor relationships and participating in donor cultivation, solicitation, and stewardship.
Strong communication and interpersonal skills.
Experience using email marketing platforms, social media, and digital communication tools to engage supporters and advance fundraising goals.
Excellent organizational and project management abilities.
Comfortable working both independently and collaboratively.
Curiosity, initiative, sound judgment, and a sense of humor.
A commitment to Chewonki’s mission and values.

Preferred experience includes:

Mailchimp or similar email marketing platforms
Social media content creation and scheduling
Salesforce or other constituent relationship management (CRM) systems
Writing for fundraising, alumni relations, stewardship, or nonprofit communications

Prerequisites:

Must be at least 21 years old
Must pass a criminal background check, including motor vehicle record
Valid Driver’s License approved by Chewonki’s insurance carrier

Position Details

Full-time, year-round position
Location: Hybrid schedule with regular presence on the Chewonki campus in Wiscasset, Maine
Reports to: the Director of Philanthropy and Alumni Engagement

Starting Salary: $58,656/Annually

Competitive Benefits package, including health, dental, vision, and life insurance, paid time off, 403(b) retirement plan, professional development support, and meals while on campus

Chewonki alumni and former staff who bring relevant fundraising, advancement, or relationship-management experience are encouraged to apply.

If you are excited about helping people stay connected to a community that has shaped generations of lives, we encourage you to apply.

Chewonki Foundation Inc

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Associate Director of Philanthropy & Alumni Engagement