We are hiring our first headmaster! We are opening in fall 2026 with a freshman and sophomore class. We anticipate enrolling 10 to 15 students in the first year and growing from there. We are finalizing a temporary location. We would like someone who can start in January on a stipend basis with plans to start full time in May or June 2026, following our planned vision dinner to raise a majority of our funds. The headmaster will work closely with the founding board to implement the Founders' vision.

Full details at CatholicJobs.com. Head of School (Hammond, IN) » CatholicJobs.com - Catholic Jobs Online

Chesterton Academy of St. Nicholas seeks a freelance fundraising advisor to help us organize several events in Northwest Indiana. Specifically, we are looking for someone to help us organize a vision dinner to bring in local foundations and business leaders who can make high-dollar donations. We also would like to organize several other fundraising events to help us build up our supporter base ahead of a fall 2026 launch.

We are a joyfully, classical high school in the Catholic Tradition with a higher purpose, raising up a new generation of joyful leaders and saints.

There is the potential for this to turn into a regular position.

Applicants must be practicing Catholics and familiar with Chesterton Academy, or at least the classical education model. The ideal candidate has ties to the Northwest Indiana business community and experience fundraising for schools, churches, pro-life pregnancy centers, or similar organizations.