Regional Outside Sales Specialist, Educational Services - Chicago

This position requires the employee to reside in the Chicago, IL area and involves local travel, approximately 80–90% of the time, or 4–5 days per week in the field. Join Aya Healthcare, winner of multiple Top Workplace awards! The Regional Outside Sales Specialist, which is formally titled Regional Client Partnership Specialist, Educational Services, is Aya Education’s field leader and plays a central role in expanding our presence within school districts across the region. This position is responsible for developing and maintaining strong district partnerships, assessing full-scope staffing needs, generating job requests, and identifying opportunities for long-term, scalable workforce solutions. Most of your week will be spent onsite in schools and district offices, meeting with SPED Directors, HR leaders, SELPA administrators, Principals, and other key decision-makers. You’ll serve as the face of Aya Education in your region and help ensure districts have access to qualified special education and therapy professionals who support meaningful outcomes for students from early childhood through age 21. Who We Are: We’re a $8+ billion, rapidly growing workforce solutions provider in the healthcare industry. We deliver tech-enabled services that help healthcare organizations meet and manage their contingent labor needs. We build and manage tech-enabled marketplaces for national and local healthcare talent and deliver contingent labor management solutions through our proprietary software platform. At Aya, we’re obsessed with creating exceptional experiences for our clients, clinicians and employees. In fact, we put employee satisfaction above all else. Our team members are responsible for incomparable customer experience and we know that happy employees are critical to maintaining happy clients. We foster an entrepreneurial, high-energy, low-bureaucracy culture and value innovative thinking and creative problem solving. We embrace diversity in thought and backgrounds unified by a commitment to high achievement. When you join Aya, you’ll be surrounded by teammates who care about you as an individual and leaders who will help you grow both personally and professionally. Responsibilities: New Business Development Conduct 5–8 daily walk-ins or 3–4 scheduled meetings with district leaders in order to generate new business Identify, pursue, and secure new business opportunities within assigned markets Build and maintain a healthy pipeline of target districts in order to win new business Generate new job orders across SPED, paraeducator, therapy, behavioral health, and general education support roles Recognize early indicators that may suggest future MSP opportunities Relationship Building and Account Expansion: Develop strong, long-term partnerships with district leadership Visit clients and prospects 4–5 days per week to build familiarity and deepen relationships Conduct onsite assessments to uncover unmet staffing needs and expand existing accounts Serve as Aya’s local market representative and a trusted partner to district teams Collaboration and Cross-Functional Alignment Partner with Account Managers to ensure job orders are filled quickly and accurately Work closely with internal teams, including Recruitment, AM Leadership, Compliance, and Licensing, to support overall account growth Maintain accurate documentation of walk-ins, meetings, and district insights in HubSpot Educate districts on LotusOne, demonstrate platform value, and support onboarding Field Intelligence and Strategic Insights Track and report on competitive activity, district budget cycles, and hiring trends Identify patterns such as high call-offs, multi-agency usage, inconsistent fill rates, or staffing gaps Use field insights to inform long-term MSP strategy Representation and Events Represent Aya Education at conferences, regional events, and district engagements Deliver polished presentations and talking points tailored to school leadership Increase awareness