By Ray York, Business Counselor for the Sheboygan County Economic Development Corporation (SCEDC) and the Small Business Development Center (SBDC) at UW-Green Bay
Sheboygan County, WI – Accelerate Sheboygan County, powered by the Sheboygan County Innovation Council and the Sheboygan County Economic Development Corporation (SCEDC), is proud to highlight the launch of Go With Rosie, a Sheboygan County-based startup helping families discover, plan, and book trips with ease. The platform is now live at gowithrosie.com.
Founded by Sheboygan native Tyler Heilberger, Go With Rosie was built from a simple but powerful idea: make family travel planning easier by leveraging real experiences from real families. After returning to Sheboygan County and working remotely during the COVID era, Heilberger noticed how valuable personal travel recommendations were and saw an opportunity to scale that experience through technology.
Go With Rosie acts like a trusted friend who has already done the research. The platform allows families to quickly build itineraries, evaluate destinations using a family-friendliness scoring system, and book accommodations without the typical hours of research. The platform is free to use, with revenue generated through hotel booking commissions rather than subscriptions or paid rankings.
“We’re helping create the conditions for meaningful family memories,” said Heilberger. “When we take the stress out of planning, parents can focus on being present, and that’s where the real value is.”
Go With Rosie officially launched on March 18 and is already focused on scaling across the United States, with long-term ambitions to become a global platform for family travel planning. The company remains rooted in Wisconsin, with approximately 80% of its team based in the state.
The company has also begun attracting national attention, recently being featured in PhocusWire, a leading travel industry publication, highlighting the platform’s potential to reshape how families plan trips.
Go With Rosie represents the type of high-growth enabled entrepreneurship that Accelerate Sheboygan County was designed to support. Through pitch competitions, mentorship, and programming, the Innovation Council helped Tyler refine his concept, while additional support came through an Accelerate Sheboygan County Technical Assistance Grant and Product Development Loan, helping move the business from idea to launch.
“Go With Rosie is exactly the kind of company we want to see come out of Sheboygan County,” said Justin Vannieuwenhoven, Chair of the Sheboygan County Innovation Council. “It’s a scalable, technology-driven idea rooted in a real-world problem, and Tyler has done an exceptional job taking it from concept to launch. This is a great example of how our local ecosystem can support entrepreneurs building solutions that reach far beyond our region.”
“The SCEDC, Small Business Development Center at UWGB, and the Innovation Council gave Go With Rosie something you can’t buy: honest feedback, real support, and people who genuinely wanted to see a local company succeed,” said Heilberger. “They helped turn an idea into a business.”
As Go With Rosie continues to grow, the company is seeking community support through user engagement, encouraging families to share travel experiences and help strengthen the platform’s recommendations.
Go With Rosie is part of a growing wave of innovative startups choosing to build in Sheboygan County, demonstrating that scalable, technology-driven companies can launch and thrive in smaller communities with the right support systems in place.
About Go With Rosie
Go With Rosie is a family-focused travel planning platform that helps users discover, plan, and book trips quickly and confidently. Using real-world insights and a proprietary scoring system, the platform simplifies travel planning for families of all sizes and budgets. For more information, please visit gowithrosie.com.
About Accelerate Sheboygan County
Accelerate Sheboygan County is a county-wide entrepreneurship initiative powered by the Sheboygan County Innovation Council and the Sheboygan County Economic Development Corporation. The program connects entrepreneurs with mentorship, capital resources, events, and community support to help launch and grow businesses.
