Red Caboose Child Care Center, Inc.

Executive Director

The QTI Group has exclusively partnered with Red Caboose Child Care to recruit for their new Executive Director. The Executive Director of Red Caboose Child Care will lead and support a devoted team while serving as liaison with the board, its committees, parents, and the community. The Executive Director will report directly to the Board of Directors and will supervise those who manage the child care center and school-aged programs. This includes directing administrative, fiscal, and operational functions of the organization. They will assure programming directors are meet licensing and accreditation requirements/standards, and maintain an exceptional and beneficial learning environment for the children.

The Executive Director will be responsible for driving the fund development efforts, leading a capital campaign and serving as a key player in the transition plan to a new facility. As the face of Red Caboose Child Care, the Executive Director will work to maintain and build upon relationships in the community with other area nonprofits, private, and civic organizations.

This person will be a servant leader who will support the vision and mission by treating each child, family, and staff member with respect, dignity, and compassion, accepting cultural differences, special needs and diverse family structures. The Executive Director will be visible and approachable, portraying humility, honesty, enthusiasm, a sense of humor and a strong work ethic to ensure a safe diverse environment.

Essential Job Duties and Responsibilities
  • Promote an organized culture that fosters a passion for the mission, collaboration, open and frequent communication, creative thinking, and a common organizational vision.
  • Maintain accountability for the operational and fiscal integrity of the organization. Guide and support the staff and Board of Directors in establishing goals and developing policies, procedures, budgets, and programs that fulfill the mission of Red Caboose Child Care.
  • Work in partnership with the Development project manager(s) to work toward reaching the capital campaign goals. Enhance long-term strategic fundraising efforts with clear strategies and strong relationships with individual and corporate donors.
  • Serve as the face of Red Caboose Child Care; build and maintain relationships throughout the Madison area by working closely with other professional, civic, and private organizations. Remain active and visible in the community among a diverse group of children, parents, and staff.
  • Lead the vision for the future of Red Caboose; lead a strategic planning process to identify changes in strategy and direction for the long-term health of Red Caboose and implement that vision with the board and staff.

  • Provide oversight of the financial operations of Red Caboose; create and manage the annual budgets, monitor actual financial performance relative to budgets, provide required reports to the Board and outside agencies.

Skills, Qualifications, and Experience

  • Authentic passion for the Red Caboose Child Care mission.
  • Strong interpersonal skills to compellingly communicate the vision and value of Red Caboose Child Care across a variety of key stakeholder groups, building relationships across business and philanthropic communities, city leaders, the academic community, and the public.
  • Experience leading a nonprofit organization, including working with a Board of Directors, engaging future board members, and leading/managing a staff.
  • Proven ability to foster a healthy organizational culture, with the management skills to encourage teamwork and collaboration to meet goals, and the emotional intelligence to inspire, support, and develop staff.
  • Proven experience in successful fund development, grant writing, donor relations, advancement and philanthropy with a consultative, collaborative and strategic approach. Experience leading a capital campaign strongly desired.
  • Experience leading the development of a strategic plan with board and staff, with the project management skills to ensure it is successfully implemented.
  • Strong financial and operational acumen; direct experience with budget development and management, and P&L oversight.
  • A proven penchant for continual learning, to creatively evolve to meet the needs of the future and the ability to successfully lead those new initiatives.
  • Bachelor’s degree from an accredited college required.

Qualified individuals interested in being considered for the position are invited to submit their resume to:



Red Caboose's Child Care Center

Float Teacher

Our Float Teacher will work on an on-call basis in different classrooms with children who vary in age from 9 months to 6+ years. This is a full-time position. We accept candidates for this position who fulfill at least the minimum licensing requirements for a Preschool Teacher in Wisconsin (preferred), although candidates with degrees in related fields are also welcome to apply.

Full Position Description: Float Teacher

Submit application to Preschool Program Director


Permanent Teacher in our Bumble Bee (3 year old) Classroom 

Join an amazing team of teachers!  Red Caboose is a play-based, child centered licensed and accredited program.  We have a strong history of providing excellent care and education for our children as well as a strong commitment to the care and well being of our staff.   We offer part time and full time opportunities with excellent health and retirement benefits on top of a living wage.   Red Caboose is looking for experienced teachers who  who fulfill at least the minimum licensing requirements for a Preschool Teacher in Wisconsin.   This position is represented by the Wisconsin Child Care Union.

Full Position Description: Full Time Teacher

Submit application to Preschool Program Director


Substitute Teachers

Our Substitute Teachers will work on an on-call basis in different classrooms with children who vary in age from 9 months to 6+ years. We accept candidates for this position who fulfill at least the minimum licensing requirements for a Preschool Teacher in Wisconsin (preferred), although candidates with degrees in related fields are also welcome to apply.

Employment Application: Substitute Teacher

Submit application to Preschool Program Director



Red Caboose's School Age Program

After-School Teachers
We are looking for adults with professional experience who are energetic, creative, & dedicated to work with children in grades K-5 from a highly diverse group of socio-economic backgrounds.

Employment Application: After-School Teacher

Submit application to School Age Program Director



Red Caboose's Camp Caboose Program

2020 Camp Caboose Captains and Counselors
We are not hiring for Camp Caboose 2020 just yet.  Please come back in early 2020 to see what awesome job opportunities we have for next summer!