Secure SPED Transportation Contracts with Chicago Suburban Districts

We are expanding our business into special education (SPED) school transportation, focusing on IEP students. Our goal is to secure contracts with school districts in the Chicago suburbs (North, Northwest, West, South) that need help filling existing transportation contracts or covering hard-to-fill SPED routes.

We aim to start small with a pilot program of 3-4 drivers for SPED route coverage to demonstrate reliability, compliance, and consistency while addressing immediate district needs.

We are seeking a freelancer with experience in:
- District-level outreach and building trust with key decision-makers (transportation directors, SPED directors, procurement officers, district leadership).
- Identifying districts with urgent transportation needs such as driver shortages, overflow, out-of-district runs, or other gaps.
- Developing compliant and district-ready transportation programs.
- Supporting contract acquisition strategies and guiding us through the process of securing our first contract.

The freelancer will also assist in contacting districts, building relationships, and identifying the right opportunities to establish a foothold. The focus is on creating a strong foundation for long-term partnerships by starting small and scaling as we prove our value.