Location:Westbrook, Maine
Reports To:Board of Directors
Status:32 hours/ week

About Discover Downtown Westbrook

Discover Downtown Westbrook (DDW) is a nationally accredited Main Street organization dedicated to strengthening downtown Westbrook through community and economic development, placemaking, community engagement, and business support. As one of Maine's ten Main Street communities, DDW works in partnership with Main Street America and the Maine Downtown Center. DDW’s mission is to engage residents, the business community, and the municipality to create a positive downtown environment by recruiting and retaining businesses, drawing people downtown by hosting and promoting events, and making downtown a walkable, livable, thriving destination.

DDW's work is guided by three Transformational Strategies: promoting the Presumpscot River and Riverwalk as a family-friendly destination, strengthening Westbrook as an attractive place for residents and businesses, and cultivating an arts and culture scene that celebrates Westbrook's creativity and diversity.

Position Summary

The Executive Director serves as the chief executive officer of Discover Downtown Westbrook and is responsible for advancing the organization's mission, strategic priorities, and long-term health. The Executive Director leads organizational operations, fundraising, economic development initiatives, marketing, placemaking efforts, events, and community engagement activities. Reporting directly to the Board of Directors, the Executive Director works closely to build strong relationships with volunteers, businesses, community partners, funders, Westbrook residents, and the City of Westbrook.

Key Responsibilities

Organizational Leadership

Provide strategic leadership and day-to-day management of the organization.
Support and collaborate with the Board of Directors in governance, planning, and policy implementation.
Maintain Main Street America accreditation and compliance with Maine Downtown Center requirements.
Develop annual work plans, budgets, reports, and organizational priorities.
Work closely with the municipality to focus on the community and economic needs and development of Westbrook’s downtown.

Financial Management and Fundraising

Collaborate with the Treasurer and Finance Committee to develop and manage the annual operating budget.
Partner closely with the Board and the Fundraising Committee to strengthen the organization’s financial foundation and help grow the organization and sustain its funding stability into the future.
Work to develop and implement a fundraising plan that includes grants, sponsorships, partnerships, events, campaigns, and donor cultivation.
Build relationships with businesses, foundations, government agencies, and community partners to secure financial support.

Economic Development and Community Revitalization

Advance projects that strengthen downtown vitality, tourism, entrepreneurship, and investment.
Lead and continue to support business initiatives including the Westbrook World Markets Project, community tourism programs, placemaking efforts, entrepreneurship initiatives, business community networking events, and the City of Westbrook’s Business Retention and Recruitment efforts.

Marketing and Communications

Serve as the primary spokesperson for the organization.
Oversee the implementation of marketing, public relations, branding, social media, newsletters, website content, and community outreach.
Promote downtown businesses, events, and initiatives while strengthening the Discover Downtown Westbrook brand.

Events and Placemaking

Provide leadership and oversight of staff and committee leadership for the successful delivery of DDW's signature events, including the Vallee Square Summer Concert Series, Monsters Run the River, Winterfest and the Westbrook Discovered Gala.
Oversee the Westbrook Common Placemaking Initiative, other smaller events, and related community activation efforts.

Committee and Volunteer Engagement

Support the organization's primary standing committees: Design & Art, Economic Vitality, Promotions, and Organization Committees.
Recruit, engage, and develop Board members, committee members, volunteers and community leaders, through relationship building, and by supporting a nominations effort throughout the year.
Foster collaboration among businesses, residents, municipal leaders, and community organizations.

Staff Supervision

Supervise and support the staff, specifically the Event and Volunteer Coordinator.
Expand staff capacity through interns, VISTA fellows, and contract workers as the need, funding, and availability arise, as approved by the Board.
Ensure effective planning and execution of events, communications, volunteer programs, placemaking activities, and committee initiatives.
Promote a collaborative and high-performing organizational culture.

Qualifications

Bachelor's degree in nonprofit management, business, marketing, community development, urban planning, public administration, or a related field; equivalent experience considered.
Three or more years of leadership experience in nonprofit management, downtown revitalization, economic development, fundraising, community engagement, or a related field.
Demonstrated success in fundraising, project management, partnership development, and volunteer leadership.
Strong communication, organizational, and relationship-building skills.
Familiarity with Main Street America principles, placemaking, economic development, and historic preservation is preferred.
Ability to work evenings and weekends for meetings, events, and community activities.

Compensation and Benefits

Salary Range:$30-$36/ hour ($49,920-$59,904) commensurate with experience.

Benefits include paid time off, health care stipend, technology stipend, professional development opportunities, flexible scheduling, and other benefits as approved by the Board.

How to Apply

Please submit a cover letter, resume, and three professional references to jobs@downtownwestbrook.com. The position is open until filled.Applications will be reviewed on a rolling basis, and those received prior to June 23, 2026 will receive priority consideration.

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Executive Director Discover Downtown Westbrook