Port Main Street director out after just months on the job

Port Washington Main Street Inc., which is charged with promoting downtown and making it a prosperous place for businesses, residents and tourists, is undergoing a change of its own.

Jenna Cawlfield, who was hired as the organization’s executive director in November, left that position on Monday, Nate Scherper, president of the Main Street Board of Directors, said. He declined to comment on why she left.

The board appointed Amanda Baldwin, the organization’s office manager, as the new executive director effective immediately, Scherper said.

“Amanda has been closely involved in our operations and partnerships during her time with Main Street,” he said. “The board is confident in her ability to provide strong leadership and continuity for the organization.

“We think she’s doing a great job. She’s already been doing a lot of work with the team and has had some really good relationships with businesses and other stakeholders.”

Baldwin joined the Main Street team in September 2025 after spending several years in education, teaching in both Minneapolis and Milwaukee before moving to Port Washington in 2022, according to Main Street.

In addition to Baldwin, Port Main Street is staffed by Assistant Director Martin Schmit, who has been with the organization since 2021 and largely handles media outreach and sponsorships, Scherper said.

“Port Washington Main Street remains focused on supporting our downtown businesses, strengthening community partnerships and advancing the vibrancy of Port Washington’s Main Street district,” Scherper wrote in a letter to downtown businesses. “This leadership transition does not change our strategic direction or our commitment to the community we serve.”

This is the second change in leadership at Port Main Street Inc. in the last year.

Kristina Tadeo, who had been Main Street’s executive director since 2021, left the organization in November to become executive director of the Port Washington Tourism Council, a role she said would allow her to make better use of her skills in marketing.

Cawlfield, a former production manager for Gartner, an information technology research company, succeeded Tadeo at Main Street.

She had spent the previous six years as a stay-at-home mom but applied for the director’s job when she decided to get back into the workforce.

“I really missed the day-to-day process of being involved in something bigger than me,” the Belgium resident said when she was hired. “I wanted to be involved in something that was making a lasting impact.”

Port Washington has been a Main Street community since 2008. Port Main Street Inc. is funded in large part by the Port Washington Business Improvement District.

It is one of 36 Main Street communities in Wisconsin.