Senior Director of Development

Senior Director of Development

Goodwill Southwest Florida

Reports to: President/CEO

Location: Southwest Florida

Employment Type: Full-Time | Exempt

Lead Transformational Philanthropy. Shape the Future of Goodwill in Southwest Florida.

Goodwill Southwest Florida is seeking a Senior Director of Development-a strategic, relationship-driven fundraising executive-to lead and expand a comprehensive philanthropic program during a pivotal period of organizational growth.

This is a rare opportunity to play a central role in advancing workforce development, education, and human services across a five-county region while helping lead a transformational $30 million capital campaign. Working in close partnership with the President/CEO, Board of Directors, and senior leadership team, the Senior Director of Development will drive philanthropic revenue, strengthen donor engagement, and build long-term fundraising capacity.

We are looking for a confident, forward-thinking fundraiser who can move seamlessly between strategy and execution-someone who inspires donors and volunteers, coaches and develops staff, and personally closes leadership-level gifts.

Key Responsibilities

Strategic Fundraising Leadership

• Design and execute a comprehensive, multi-channel fundraising strategy aligned with organizational priorities.
• Grow annual contributed revenue across individual, corporate, foundation, and community-based donors.
• Establish clear goals, performance metrics, and accountability systems to drive results.
• Strengthen development infrastructure, including donor pipelines, prospect strategy, CRM utilization, and stewardship practices.

Capital Campaign Leadership

• Partner with the CEO and Board to plan and lead a $30 million capital campaign.
• Manage campaign strategy, prospect movement, volunteer engagement, and gift tracking.
• Prepare executive and volunteer leaders for high-level donor conversations, solicitations, and stewardship.
• Personally manage and solicit a portfolio of top campaign prospects, including six- and seven-figure opportunities.

Major & Leadership Giving

• Identify, qualify, cultivate, solicit, and steward high-capacity donors.
• Build and sustain a robust leadership annual giving pipeline.
• Lead disciplined moves management and donor engagement strategies to maximize impact and long-term relationships.

Board & Executive Partnership

• Serve as a trusted advisor to the CEO on fundraising strategy and donor relationships.
• Engage and support Board members in fundraising efforts, donor introductions, and stewardship activities.
• Develop briefing materials, talking points, and strategies to support leadership engagement.

Team Leadership & Culture

• Lead, mentor, and develop a high-performing development team, including the Development Officer and Grants Manager.
• Foster a collaborative, donor-centered culture rooted in accountability and professional growth.
• Clarify roles, align resources, and support staff development to achieve ambitious goals.

Community Visibility & Partnerships

• Represent Goodwill Southwest Florida with donors, foundations, civic leaders, and corporate partners.
• Build meaningful community relationships that elevate mission awareness and philanthropic investment throughout the region.

Required Qualifications

• Minimum 8 years of progressive fundraising leadership experience.
• Demonstrated success securing major and leadership annual gifts.
• Proven experience leading or playing a senior role in a capital campaign or large-scale fundraising initiative.
• Strong track record in prospect identification, cultivation planning, solicitation, and closing gifts.
• Experience managing and developing fundraising teams.
• Success partnering with CEOs, Boards, and senior-level volunteers.
• Excellent communication, presentation, and relationship-building skills.
• Strong command of CRM systems, prospect pipelines, and fundraising analytics.

Preferred Qualifications

• Experience in human services, workforce development, education, healthcare, or complex community-based nonprofits.
• Knowledge of the Southwest Florida philanthropic landscape.
• CFRE or other advanced fundraising credentials.

Why Join Goodwill Southwest Florida?

This role offers the opportunity to:

• Lead a landmark capital campaign with lasting regional impact.
• Partner closely with an engaged CEO and Board.
• Build philanthropic support that directly transforms lives and strengthens communities.
• Play a key leadership role in a respected, mission-driven organization with strong momentum and growth ahead.