People Operations Specialist

About Stepful

Stepful is reimagining allied healthcare training by offering affordable, online, instructor‑led, and AI‑supported programs that help learners—regardless of background or circumstance—launch high‑demand healthcare careers.

In addition to our direct‑to‑consumer training, Stepful partners with leading healthcare institutions to address the growing national shortage of healthcare workers. Our graduates, including Medical Assistants, Pharmacy Technicians, Nurses, and more, form the talent pipelines at major employers like CVS, NY‑Presbyterian, HCA, Providence, and Walgreens.

Stepful is backed by Y Combinator, Reach Capital, and Alley Corp, with a recent $55M Series C led by Oak HC/FT. We were named the #1 EdTech company in the U.S. by TIME for 2025.

We’re improving access to quality healthcare for everyone, everywhere, and improving access to healthcare careers for those who need them most.

• Care first We do whatever it takes for our students to succeed.
• Learn quickly We test, learn with data, and iterate.
• Build together We win when we rely on each other.
• Own it We show up, take initiative, and show pride.

Stepful is hiring a People Operations Specialist to join the People Operations team as a hands‑on, execution‑focused resource across a broad range of People programs and processes. This role sits at the intersection of HRIS administration, payroll operations, workforce lifecycle management, and People program support.

This role will serve as the primary People Ops point of contact for our frontline workforce—coaches, instructors, and contractors—owning their lifecycle end‑to‑end and escalating to the Associate Director of People Operations as needed. Alongside that primary ownership, this role will support the execution of broader People programs and initiatives that impact the full employee population.

This hybrid role (3 days/week at our Fenton, MO campus) reports to the Associate Director, People Operations.

• Own administration and ongoing optimization of Rippling across contractor and instructional staff populations, with support for HQ employees.
• Maintain high data integrity across all employee and contractor records—ensuring records are accurate, complete, and audit‑ready at all times.
• Build and improve automations, workflows, and system processes as the workforce scales.
• Serve as the internal go‑to for system questions, troubleshooting, and process guidance.
• Support key annual processes including open enrollment and any HRIS migrations or implementations.
• Partner with the compliance and legal teams to build and maintain Rippling workflows that capture the specific reporting requirements, classification rules, and documentation needs of our instructional workforce.

• Support payroll processing for hourly and program‑based instructional staff in Rippling, ensuring accurate and timely pay runs.
• Manage compensation and rate changes, ensuring updates are reflected correctly in Rippling and processed on cycle.
• Coordinate contractor invoice and payment workflows, including final pay processing for offboarding contractors.
• Identify and resolve payroll discrepancies in partnership with Finance and the Associate Director of People Operations.

• Manage onboarding workflows for contractors and instructional staff—ensuring agreements are executed, documentation is complete, and system access is in place before day one.
• Own ongoing lifecycle administration: compensation changes, role or scope changes, status changes (including contractor‑to‑employee transitions), and record updates.
• Serve as the primary point of contact for employee relations matters for frontline team members—including performance management documentation (e.g., PIPs), manager guidance, benefits questions, and day‑to‑day HR support—escalating to the Associate Director as needed.
• Support leave management for frontline staff—tracking leave requests, coordinating documentation, and ensuring accurate reflection in payroll and records.
• Manage offboarding for contractors and instructional staff—documentation, system access removal, final pay…