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Meet Dylan

Dylan and others stand with a sign that says "Dylan Helmenstine Wisconsin Heights School Board 2023"

Getting Involved

Dylan took the lesson of social responsibility seriously and participated in public service as soon as he could. At age six, his favorite game to play with his friends was “Nations”, a game of his own creation that involved selecting a country to represent and then writing out a code of law and reform policies. In middle school, he sat on the student council, and by high school, he was Class President for all four years. Dylan reached for every opportunity he saw that would let him serve his community and help those around him.

 

After high school graduation, he attended UW-Madison and earned his Undergraduate degree in a dual study of Economics and Political Science. A year later, Dylan graduated with his Master’s of Public Affairs from the La Follette School of Public Policy at UW-Madison. 

 

Dylan has always loved to learn, and he credits part of that love to the public school teachers he had starting in Elementary School. Their mentorship and shared love of learning stuck with Dylan and after graduation he returned to Black Earth to serve the community that had helped serve him for so long. 

Young Dylan

Dylan grew up in the small, rural Wisconsin community of Black Earth where his family has been for three generations. His parents were raised on farmsteads on different sides of the same valley, just a few miles from where Dylan currently lives. Growing up and living in a small town in Wisconsin shapes how he views public service. The best things about the community happen because people decide to show up. High school team fundraisers, the annual summer parade, even the food banks are all made possible by dedicated volunteers who don’t ever ask for thanks. 

His family further reinforced the significance of helping others and being active within the community. Dylan’s mother, Ilene, works as an accountant and coached volleyball in the Wisconsin Heights School District for ten years. His father, Pat, is a proud union plumber who serves on the Town of Black Earth’s Plan Commission and is the local Snowmobile Club Trail Master. His older sister Rhea has coached middle school volleyball and can always be found volunteering at local fairs and events. On top of all that, Dylan has dozens of aunts, uncles, and cousins who all serve their communities in different ways. Dylan has been surrounded by a sense of service his entire life. To him, public service is carrying on a long family tradition. . 

Dylan and seven members of his family pose for a group photo
Dylan as a child with a big smile

“My family taught me to always work hard, to be a good neighbor and friend, to show up for family, and to serve in whatever way I can.”

Service to his Community

Dylan doesn’t hold back when living his values. He knows that no job is too small, and he steps in to help whenever he can.

In serving others, Dylan currently holds several elected and appointed positions. 

School Board- Wisconsin Heights School District

  • Dylan is an elected school board member for the Wisconsin Heights School District, which includes Black Earth, Mazomanie and the surrounding townships. He most recently spearheaded an emergency resolution during the Wisconsin Association of School Boards Conference that called for the State to keep its promise for Special Education funding for Wisconsin’s public schools. 

Village Board- Village of Black Earth

  • Dylan is a village board trustee for Black Earth. In his time on the board he has worked on zoning codes to encourage the construction of affordable housing and has been updating the Black Earth emergency response plan. 

President - Dane County District 1 EMS Board

  • As president, Dylan has worked with the board to manage the transition from all-volunteer staff to a hybrid employee model. He has prioritized providing affordable, reliable benefits for their paid staff. Dylan is a strong advocate for increased EMS support to make sure skilled responders arrive when you call 911.

Chair - Black Earth Plan Commission

  • Dylan chaired the plan commission as the village updated its zoning codes and land use codes. He is working to create a five-year housing action plan, which will help take concrete steps toward bringing more homes into Black Earth that are affordable to those in the community. 

Chair - Black Earth Economic Development Committee

  • As chair, Dylan has focussed on the construction of a multi-use trail to connect the major communities along the Black Earth Creek. This trail is projected to be an economic driver for the region as it connects the downtowns through an easily traversable pedestrian path.

Chair - Black Earth Emergency Management Committee

  • The board works with the fire department, public works director, and emergency response manager to update the Black Earth Emergency Response Plan and make sure the village is prepared for a wide variety of situations. 

Teacher’s Retirement Board - Wisconsin Employee Trust Funds

  • Dylan was appointed to the Teacher’s Retirement Board by the governor in 2024. The board performs oversight of the Employee Trust Funds and the State of Wisconsin Investment Board staff as they manage and invest the employee trust and offer benefits to the public employees of Wisconsin.

Policy and Resolutions Committee - Wisconsin Association of School Boards

  • Dylan worked with school board members from across the state to impartially review proposals to the Wisconsin School Board Delegate Assembly.  Dylan used his policy and procedural experience to develop and propose several improvements to the committee’s operations. This has strengthened the Association’s efforts and influence is working to defend and fund public schools in Wisconsin.

Board of Control - Cooperative Educational Service Agency  (CESA 2)

  • CESA 2 includes a number of school boards and focuses on providing efficient solutions for school districts. CESA empowers districts to combine purchasing power to hire professional staff that small districts could not individually afford as well as provide an opportunity for knowledge sharing amongst the districts. The Board of Control oversees the shared district funds and manages the agency budget. 

"When you look behind the curtain, you can see just how much better we could do. It is clear how many more people we could help if our laws and systems were built to benefit the many. If our laws were support beams for the people in our state instead of brick walls in our way."

Pulling Back the Curtain 

After graduating from UW-Madison with a Master's of Public Affairs, Dylan worked for the State as an Auditor and Financial Analyst for Wisconsin Medicaid. Through both local government and state programs, Dylan has seen firsthand how local communities are being held back. 

Wisconsin’s current system is full of outdated funding mechanisms, red tape, and a long history of broken promises that sideline Wisconsinites in favor of consultants, corporations, and big money interests. It is a system that pushes our communities to the brink, property taxes through the roof, and affordability out of reach for families all across Wisconsin.

Dylan knows a better future is possible, and he will work tirelessly to reach it.

It starts with being honest about the incredible need for structural change, and working together to achieve it. Dylan wants to make government work for the people of Wisconsin, so families, schools, and communities have the support they need to thrive.

To read more about Dylan’s top priorities, visit his priorities page here:

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