Executive Director

Driftless Development, Inc. (DDI)
Crawford County, Wisconsin

Position Summary

DDI seeks an energetic, strategic, and collaborative leader to serve as its next Executive Directorin Prairie du Chien, Wisconsin. The Executive Director is the chief executive and primary spokesperson of DDI, responsible for driving economic vitality, strengthening business and community partnerships, and advancing projects that enhance the quality of life throughout Crawford County.

This role also includes direct oversight of Driftless Downtown Prairie du Chien, a designated Wisconsin Economic Development Corporation (WEDC) Connect Communities program. The Executive Director will champion downtown revitalization, small business support, and placemaking initiatives, ensuring strong alignment between county-wide economic development and local downtown priorities.

Key Responsibilities

Economic & Community Development

• Support county-wide business recruitment, retention, and expansion strategies, in partnership with local government, chambers of commerce, and regional/state agencies.
• Support the growth of entrepreneurs and small businesses by facilitating access to DDI’s Business Development programs and coordinating technical assistance through key collaborative partnerships.
• Advance workforce development, housing, and infrastructure initiatives to strengthen the region’s competitiveness.

Organizational Leadership & Management

• Provide vision, strategic leadership, and management of DDI’s programs, operations, and outside consultants including DDI’s Marketing Manager, Downtown Events Manager and Farmers Market Manager.
• Report to and work closely with the Board of Directors to implement the organization’s mission and annual work program.
• Champion innovation and implementation—transforming ideas into actionable initiatives that strengthen the Crawford County economy.
• Manage organizational finances, including budgeting, grant reporting, and compliance with nonprofit best practices. Ensure the organization’s financial health by reviewing budgets, analyzing outcomes, and evaluating the fiscal viability or mission alignment of programs and events.
• Develop and strengthen relationships with investors, donors, and grant funders while identifying new prospects and securing grants, sponsorships, and local fundraising support to advance DDI’s mission and growth.
• Provide strategic leadership and develop creative programming to address community needs and advance the organization’s mission. Establish clear goals, track measurable outcomes, and report achievements to the board and community to demonstrate and enhance impact.
• Oversee DDI’s digital communications and marketing strategy, ensuring the website, social media, and publicity efforts effectively advance organizational goals and community and stakeholder engagement.

Community Leadership

• Oversee all aspects of the Connect Communities program, including support for the Thursday Night Farmers Market, business development, arts and cultural events, and downtown revitalization projects throughout Crawford County.
• Build and maintain strong partnerships with the City of Prairie du Chien, surrounding municipalities, business and property owners, volunteers, and community stakeholders.
• Foster consistent engagement with business owners, civic partners, and local leaders to ensure DDI’s priorities reflect and respond to the community’s real needs.
• Ensure compliance with WEDC Connect Communities guidelines, reporting, and programming.
  External Relations & Advocacy
• Serve as the primary spokesperson and advocate for economic development in Crawford County.
• Build strong working relationships with state and federal agencies, regional development partners, and local organizations.
• Represent DDI at community events, meetings, and in regional coalitions.

Preferred Qualifications

• Bachelor’s degree in business, public administration, planning, economic development, or related field.
• 5 years or more of leadership experience in nonprofit management, economic development, real estate, community planning, or related sectors.
• Demonstrated success in fundraising, grant writing, and financial management.
• Strong skills in relationship-building, collaboration, and public communication.

Knowledge of Wisconsin economic development and downtown revitalization projects, such as the Connect Communities program, revolving loan programs, and other incentives and initiatives.

Compensation

Salary commensurate with experience. The budget range for this position is between $60,000 and $75,000.

To Apply

Please submit a cover letter and resume to jobs@driftlessdevelopment.org.
Job Type: Full-time
Benefits:

• Flexible schedule
• Paid time off
• Professional development assistance

Work Location: In person