The Sheboygan Squared Business Improvement District is seeking an experienced professional
and inspirational leader to serve as Executive Director.
In 2014, the Harbor Centre Master Plan was adopted. The plan articulates the next stage of
Sheboygan’s ongoing commitment to revitalize the downtown and waterfront by leveraging the
incredible assets that set Sheboygan apart as a destination. As a recommendation of the
master plan, the business improvement district name changed to “Sheboygan Squared” to
represent two key areas of the district known as downtown and the waterfront. Prior to the
rebranding initiative in 2015, it was known as the Harbor Centre Business Improvement District.
The Master Plan identified three key core strategies: a focus on arts, culture, and food; housing
and urban development; and improved connections and cross-marketing. As a result of efforts
in line with the plan, the district is seeing approximately 260 new apartments valued at $31
million either recently completed or under construction. Fifteen new businesses have opened in
the past two years and discussions are ongoing with other businesses interested in relocating.
Other notable improvements have been increased promotion and marketing efforts; initiation of
intentional business development and recruitment strategies; as well as the beautification of the
streets and storefronts through increased flowers, new flower pots, signage, lighting, and public
art. The district has also seen the addition of a public greenspace for concerts and arts/culture
activities that has been developed to activate the cultural corridor of downtown Sheboygan and
highlight the incredible assets of the Mead Public Library, the Stephanie H. Weill Performing
Arts Center; the Above and Beyond Children’s Museum and the John Michael Kohler Arts
Center—all within a three block radius of each other.
Sheboygan Squared assists with business recruitment and retention, being the voice of the
downtown business owners, maintaining a clean and safe environment, integrating and
collaborating with the City of Sheboygan, assisting potential businesses and individuals with
property identification, and maintaining a look and feel of a vibrant and beautiful district.
The chosen individual will work closely with Sheboygan Squared Board of Directors, and interns
and volunteers. Due to the small staff size, a “hands on” attitude is imperative, while ability to
delegate and lead is important.
The qualified individual should have experience coordinating special events as well as a proven
track record of working with a diverse range of merchants, residents, and elected officials.
Fundraising and grant writing experience is preferred. The candidate must have the ability to
seek out funding sources and make professional presentations. A fiscally responsible individual
with experience in a non-profit environment is preferred.
Interested parties should submit a cover letter and resume for consideration to David Gass,
President, Sheboygan Squared Business Improvement District, 607 N. 8th St., Ste. 700,
Sheboygan, WI 53081 or by email to firstname.lastname@example.org
Position Title: Executive Director
Reports to: Board of Directors
Salary: Commensurate with Experience
Position Summary: The Executive Director leads, directs, facilitates, and inspires all personnel
and stakeholders to accomplish the Master Plan for Sheboygan Squared Business
The primary responsibilities of the position include:
Manages, leads, and directs day to day business activities and operations of the
Provides inspirational leadership and direction in implementing the Master Plan and
related objectives, priorities and goals of the organization.
Assists the City of Sheboygan Department of Planning and Development with business
recruitment and retention.
Acts as a voice and the advocate for district business owners.
Works with the Sheboygan Parking Utility on coordination of beautification and
enhancements to the streetscape.
Maintaining a clean and safe environment and maintaining the look and feel of vibrant
and beautiful district.
Fosters economic, cultural, and education vitality.
Maintains a strong and effective working relationship with leadership from the City of
Sheboygan and Sheboygan County, business and property owners within the Business
Improvement District, the Sheboygan County Economic Development Corporation,
Sheboygan County Chamber of Commerce and Visit Sheboygan, Inc.
Maintains information systems that include a database of district property and business
owners, pertinent market characteristics.
Facilitates consistent, informative and effective communications. Serve as chief
spokesman and primary advocate representing the organization across various media
platforms, government agencies, other downtown and community organizations, and
state-wide groups. Attends necessary City Council, Redevelopment Authority and other
city committees to champion downtown projects.
Prepares, oversees and implements the budget as approved by the Board of Directors.
Provides leadership to drive achievement of program goals.
Continues work on wayfinding, streetscaping and beautification for Sheboygan Squared.
Creates awareness and build consensus for Sheboygan Squared activities, programs,
services and special events.
Manages marketing, advertising, and public relations initiatives to effectively
communicate Sheboygan Squared brand and value proposition.
Increases revenues and expand funding sources to enhance the effectiveness of the
organization through grants, sponsorships, memberships, and other resources.
Maintains an understanding of zoning, development and city policies. Stay abreast of
successful downtown revitalization strategies.
Oversees the planning, implementation and follow up of the Board and committees, task
forces, presentations and numerous special events. Coordinate Board agendas,
minutes, and correspondence.
Performs other tasks as assigned by the Board and committees relevant to achieving the
objectives and purpose of the position.
Experience: Proven experience in non-profit management, self-starter, and fiscally responsible
or education in economic development, urban planning or related field. 3-5 years’ experience in
management including direct oversight of interns and volunteers, financial, and service delivery
Must be well-organized and capable of managing multiple projects simultaneously.
Possess excellent written and verbal communication skills.
Personal Attributes: Creative and innovative thinking, good promotional skills, good time
management and organizational skills, ability to work well with people, listen and communicate,
Working Conditions: Some weekend, evening and early morning time required. At times, this
may be extensive. Some travel required, physical demands include standing, sitting, balancing,
stooping, crouching, reaching, handling, speaking, hearing, seeing, lifting, carrying, pushing and
pulling. Will need to work in increment weather when required and must have or attain a current
Wisconsin Driver’s License.
Proficiencies: An eye for creative social media and marketing solutions. Experience in
updating WordPress websites, Quick Books, Publisher, Photoshop and Illustrator a plus.
Submit a cover letter and resume for consideration to David Gass, President, Sheboygan
Squared Business Improvement District, 607 N. 8th St., Ste. 700, Sheboygan, WI 53081 or by
email to email@example.com