People Operations Specialist

Stepful•St. Louis, MO

16h•$110,000 - $120,000•Hybrid

About The Position

Stepful is reimagining allied healthcare training by offering affordable, online, instructor-led, and AI-supported programs that help learners launch high-demand healthcare careers. They partner with leading healthcare institutions to address the growing national shortage of healthcare workers. Stepful is backed by Y Combinator, Reach Capital, and AlleyCorp, with a recent $55M Series C led by Oak HC/FT. They were named the #1 EdTech company in the U.S. by TIME for 2025. The company is improving access to quality healthcare and healthcare careers. Stepful is looking for mission-driven builders who thrive in fast-paced, ambiguous environments and embody their core values: Care first, Learn quickly, Build together, and Own it. This role is for 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. The role will serve as the primary People Ops point of contact for the 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 is a hybrid role, requiring 3 days/week at the Fenton, MO campus, and reports to the Associate Director, People Operations.

Requirements

3+ years of experience in People Operations, HR, or a related operational role.
Experience supporting or managing hourly workforces, contingent workers, or high-volume contractor populations.
Strong HRIS skills - Rippling experience strongly preferred; must be comfortable building workflows and maintaining data integrity, not just using the system.
Solid understanding of payroll operations, including hourly and program-based pay structures.
Exceptional attention to detail - you catch errors before they become problems.
Strong process orientation; you build structure, document clearly, and improve systems over time.
Ability to manage multiple workflows and competing priorities without dropping the ball.
Strong communication skills and comfort working across People Ops, Legal, Finance, and business leaders.

Responsibilities

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.
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 the 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.
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.
Support leave management for frontline staff.
Manage offboarding for contractors and instructional staff.
Track and manage program contract renewals for instructional staff.
Support execution of company-wide People programs and initiatives led by the Associate Director of People Operations, including performance review cycles, policy rollouts, and employee communications.
Manage logistics for the performance review cycle.
Support the preparation and distribution of People team communications and program materials across the full employee population.
Take on ad hoc People Ops projects as the team and company scale.