Vice President Rc Pilot Jobs in Chicago, IL (NOW HIRING)

Interested in this position? View the full position profile and apply here.

Aspire is seeking an entrepreneurial, systems‑minded, and growth‑oriented leader to serve as the Vice President, Program Innovation. Tasked with bridging the gap between high‑level strategy and operational reality, this leader will advance Aspire’s growth pipeline and programmatic partnerships by executing priorities set by the Executive Team and outlined in the organization’s strategic plan and 7‑year roadmap. Reporting to the Chief Program Officer (CPO) and working in close alignment with the VP, Strategic Initiatives & Partnerships, this leader will serve as the organization’s primary “incubator,” taking new concepts and turning them into actionable, scalable, and sustainable business models.

The VP, Program Innovation owns the lifecycle of all new programs—most notably the current expansion of employment services—until they reach operational maturity and stability. This leader must possess a unique approach to relationship building, acting as an external‑facing ambassador to cultivate strategic partnerships and identify new revenue‑generating opportunities that expand Aspire’s reach. Success in this role requires a candidate who can balance a growth mindset with the technical rigor needed to build the internal systems (the processes, staffing models, and workflows) that allow new initiatives to thrive before they are transitioned to the core program operations team. The VP will be responsible for building robust management systems, establishing clear guardrails and expectations for various team members, including creating a standard process for those with billable hours and caseloads. The ideal candidate is a proactive change agent who can navigate a complex cultural landscape with sensitivity and follow through.

The ideal candidate will be outcomes oriented and have a deep commitment to Aspire’s mission, demonstrating genuine care for the well‑being of the people in Aspire’s care. While it’s understood that no single candidate will bring every single skill/competency, strong candidates will offer the following skills, characteristics, and experiences:

• Bachelor’s degree or equivalent work experience required. Master’s degree in human services, public administration, business administration, social innovation, or related field, preferred.
• Minimum 10 years of progressive leadership experience in program strategy, innovation, partnerships, or related fields, required.
• Demonstrated experience designing, piloting, and scaling programs in a fast‑paced, changing, and complex environment, required.
• Experience managing strategic partnerships across sectors, required.
• Experience using data and evaluation to inform program decision‑making, required.
• Valid driver’s license with good driving record, required.
• Intermediate proficiency with Microsoft Office, required.
• Experience with innovation frameworks such as design thinking, human‑centered design, or rapid‑cycle learning, preferred.
• Familiarity with intellectual and developmental disability (I/DD) services or community‑based support, preferred.

Achieve Results: Drive the execution of business plans for new initiatives, ensuring growth targets and team member benchmarks are met even during complex pilot phases.

Build Effective Teams: Transform independent and siloed teams into a cohesive unit through focused supervision and a shared sense of purpose and assist team members to apply their diverse skills and perspectives to achieve common goals.

Cultivate Innovation: Act as an incubator, turning raw concepts into actionable services with a proactive approach to partnership development. A leader that is constantly looking for better ways to scale Aspire’s reach and impact.

Make Quality Decisions: Evaluate new program opportunities with a sharp eye for both mission alignment and sustainability. Ensure that programs are designed for long‑term success and keep the organization moving forward.

Tackle Tough Issues: This leader is direct and fair in their communication, capable of addressing departmental stagnation by providing effective coaching and setting firm professional standards.

Interested in this position? View the full position profile and apply here.