Downtown Sheboygan business opportunities given fresh push

Sheboygan Squared Business Improvement District and the City of Sheboygan have launched a retail recruitment strategy for the Downtown Sheboygan.

With over $37.1M in new housing developments scheduled to begin this summer that will house approximately 500 new people in the downtown, recruiting new retail to the downtown has been determined to be a priority.

Monica and Jim Wind of Krowin LLC have been retained to recruit retail businesses to the downtown district. Monica brings over 25 years of retail expertise with a background in franchise consultation. Jim brings over 15 years retail experience with a background in consumer and business lending.

Together, they intend to meet with successful business owners to encourage them to consider Sheboygan for their expansion plans. The revitalization of Sheboygan Squared is a labor of love to these long-time residents.

Sheboygan Squared and City officials have developed a Retail Recruitment Brochure that will share the positive news happening in Sheboygan’s downtown from the new housing opportunities, to the cultural destination, traffic drivers, access and resources. The brochure is available at

“We are excited to have retained Monica and Jim Wind to assist us with our recruitment efforts as the opportunity is now for retail businesses to consider Downtown Sheboygan for a second or third location,” explained David Gass, President of Sheboygan Squared.

Sheboygan Squared has identified 25-30 retail businesses that would fit well in the district and not compete with existing businesses. Monica and Jim Wind will visit these retailers and promote the positive aspects of the downtown Sheboygan and encourage them to consider Sheboygan as another location for their business.

Sheboygan’s downtown sees about 4,000 daytime workers, and Sheboygan County captures more than $215 million from tourists with consistent year-over-year growth.

Since 2010, Sheboygan’s room tax receipts have increased more than 65%, creating a sustainable cycle of growth in the tourism market.

Those interested in exploring the possibilities of opening a retail business in Sheboygan, may contact Chad Pelishek, Director of Planning & Development by phone at (920)-459-3383 or by email at

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