People Operations Specialist

About the role

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.

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 - 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 Ripling 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.
• Cook up 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 coordination, and agreement closure.
• Track and manage program contract renewals for instructional staff - maintaining a system of record for active agreements, renewal dates, and rate structures, and partnering with Legal to ensure renewals are executed on time.
• 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 - tracking timelines, coordinating with managers, and ensuring process runs on schedule.
• Take on ad hoc People Ops projects as the team and company scale, stepping in where execution support is needed most.

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.
• Able 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.

Qualifications

• US citizen/visa only.

Skills

• Strong HRIS skills - Rippling experience strongly preferred.
• Exceptional attention to detail.
• Strong process orientation.
• Ability to manage multiple workflows and competing priorities.
• Strong communication skills.

Benefits and Compensation

• Meaningful equity stake.
• Subsidized Medical, Dental, and Vision insurance plan options.
• 401(k).
• FSA, HSA, and commuter benefits.
• Learning stipend.
• Open vacation policy, including:
• The target base salary range for this opportunity is $110,000 - $120,000, and is part of a competitive total rewards package including equity and benefits.
• Individual pay may vary from the target range and is determined by a number of factors including experience, internal pay equity and other relevant business considerations.
• Please note we do not have a bonus structure at this time so all cash compensation will come in the form of base salary.
• The total compensation package will also include our benefits package and an equity (ISOs) package.

Pay

The target base salary range for this opportunity is $110,000 - $120,000, and is part of a competitive total rewards package including equity and benefits. Individual pay may vary from the target range and is determined by a number of factors including experience, internal pay equity and other relevant business considerations. Please note we do not have a bonus structure at this time so all cash compensation will come in the form of base salary. The total compensation package will also include our benefits package and an equity (ISOs) package.

Schedule

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