Senior Director of Development

About Winnakee Land Trust

Winnakee Land Trust protects forests, farms, wetlands, and scenic open space across the Hudson Valley while connecting people to the land through trails, stewardship, and community engagement. As an accredited land trust, Winnakee is committed to excellence in conservation and long-term stewardship.

Winnakee is in a period of strategic growth, expanding conservation impact, deepening community relationships, and strengthening long-term financial sustainability. We are seeking a Senior Director of Development to lead and evolve our philanthropic efforts during this exciting next chapter.

Position Overview

The Senior Director of Development leads Winnakee’s fundraising strategy and plays a key role in shaping the organization’s future. This senior leadership position is responsible for building and executing a comprehensive development program with emphasis on major gifts, leadership donors, institutional support, campaigns, and planned giving.

The Senior Director supervises a Development Manager who oversees development operations and the annual fund. Working closely with the CEO and Board, this role helps build a strong culture of philanthropy and ensures that Winnakee has the resources needed to advance its mission.

Key Responsibilities

Fundraising Strategy & Leadership

• Develop and implement annual and multi-year development strategies aligned with Winnakee’s strategic priorities and growth goals.
• Set and manage revenue goals across major gifts, campaigns, institutional giving, and planned giving.
• Serve as a senior advisor to the CEO on fundraising strategy and donor engagement.
• Work with the Development Committee and Winnakee’s Board to strengthen participation in donor cultivation and solicitation.

Major Gifts & Leadership Giving

• Lead the identification, cultivation, solicitation, and stewardship of major and leadership donors.
• Manage a portfolio of high-capacity donors and prospects using a thoughtful, relationship-driven approach.
• Partner with the CEO and Board members on donor strategy and solicitations.
• Identify annual fund donors with potential for increased or transformational giving.

Institutional Giving & Grants

• Provide strategic oversight for institutional giving, including foundation and public grant opportunities.
• Partner with program and finance staff to align proposals with organizational priorities, budgets, and outcomes.
• Support the development of compelling proposals and reports, while ensuring institutional funders are thoughtfully stewarded.

Campaigns & Special Initiatives

• Plan and lead fundraising campaigns and special initiatives, including capital, endowment, or programmatic campaigns.
• Translate conservation priorities and impact into compelling cases for support.
• Oversee donor-facing events and experiences that deepen engagement and commitment.

Planned Giving & Long-Term Support

• Grow Winnakee’s planned giving and legacy program.
• Identify and cultivate planned gift prospects, including long-time supporters and landowners.
• Ensure thoughtful stewardship and recognition of legacy donors.

Team Leadership & Development Operations

• Supervise, mentor, and support the Development Manager, providing strategic direction and professional development.
• Ensure strong development systems, donor stewardship practices, and data integrity.
• Collaborate with finance staff to ensure accurate gift processing, reporting, and reconciliation.

Board Engagement

• Support and engage the Board of Directors in fundraising efforts.
• Provide tools, guidance, and support to help board members succeed as ambassadors and fundraisers.

Communications Collaboration

• Collaborate with the External Affairs team to align fundraising campaigns and donor engagement efforts with organizational communications and outreach.
• Provide strategic input on donor-facing messaging and materials to ensure clarity, consistency, and impact.

Qualifications

Required

• 10+ years of nonprofit fundraising experience with demonstrated success in major gifts, donor portfolio management, and accountability for annual revenue goals.
• Proven ability to identify, cultivate, and close major gifts; comfort making direct asks and sustaining long-term donor relationships.
• Experience developing and executing fundraising plans, campaigns, and compelling cases for support that connect donor interests to organizational mission and impact.
• Experience with planned giving programs, including identifying prospects and stewarding legacy donors.
• Strong written communication skills, including experience crafting donor proposals, grant reports, and donor correspondence that are clear, persuasive, and mission aligned.
• Fluency with donor databases and prospect research tools; ability to maintain accurate pipeline records and use data to drive decision-making.
• Strong relationship-building and communication skills, with the ability to engage donors, board members, and community partners with confidence and credibility, and to align internal partners around fundraising strategy and timelines.
• Ability to manage competing priorities, multiple donor relationships, and overlapping deadlines with reliability and follow-through.
• Familiarity with how digital platforms and social media support donor engagement and organizational visibility.

Preferred

• Background in conservation, environmental stewardship, or a place-based organization, with an understanding of how land protection mission translates into donor engagement and storytelling.
• Bachelor’s degree in a related field, or equivalent professional experience in fundraising, nonprofit management, or environmental studies.
• Genuine passion for land conservation and connecting people to nature, with the ability to speak authentically about Winnakee’s mission in donor conversations and community settings.

Compensation & Benefits

Compensation includes a base salary of $90,000 to $100,000, commensurate with experience. In addition to the base salary, this role is eligible for an annual performance incentive opportunity ranging from $5,000 to $10,000. Performance bonuses are awarded based on the achievement of specific, predetermined strategic benchmarks and overall team success.

Winnakee offers a competitive benefits package and a flexible, mission-driven work environment.

Why This Role Matters

This is an opportunity to shape and grow a development program at a pivotal moment, work alongside a committed team and board, and help ensure the permanent protection of land and access to nature.