Senior Operations Manager Ai @ Stepful

About Stepful:

Stepful is a workforce platform redefining how America's largest health systems build, train, and retain their talent. Since our founding in 2021, Stepful's trained over 32,000 practice-ready healthcare workers.

Layering onto our successful direct-to-consumer training, Stepful partners with leading healthcare institutions to address the growing national shortage of healthcare workers. We're improving access to quality healthcare for everyone, everywhere, and improving access to healthcare career ladders for those who need them most.

Our students form the talent pipelines for major employers such as NY-Presbyterian, Mt. Sinai, HCA, Providence, CVS, and Walgreens. We have partnerships with half of the top 10 health systems in the US and are in process with many more.

Stepful is backed by Y Combinator, Reach Capital, and AlleyCorp, 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.

Our values:

We credit much of our success to our exceptional team. We're looking for mission-driven builders who thrive in fast-paced, ambiguous environments, and embody our four core values:

• 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.

The opportunity:

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.

What you'll do:

HRIS & People Systems

• 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.

Payroll Support

• 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.

Frontline Workforce Lifecycle

• 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.

People Programs & Cross-functional Support

• 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.

• 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, stepping in where execution support is needed most.

What Success Will Look Like

• Contractor and instructional staff records in Rippling are accurate, complete, and audit-ready at all times.

• Payroll runs for hourly and program-based instructional staff are processed accurately and on time, with discrepancies identified and resolved quickly.

• Program contract renewals are tracked proactively - no agreements expire without a deliberate decision.

• Rippling workflows and automations reflect the actual complexity of our instructional workforce, including classification rules and reporting requirements.

• Onboarding and offboarding for contractors and instructional staff is consistent, compliant, and well-documented.

• Internal stakeholders have a reliable, knowledgeable partner for People Ops questions, system issues, and process guidance.

• People program logistics - including performance review cycles and broader initiative execution - run on schedule and with consistent follow-through.

What you'll bring:

• 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.

Interview Process:

• Introductory call with a Talent Acquisition team member

• Interview with Hiring Manager

• Take-Home Assignment

• Virtual Assignment Interview

• On-Site Panel Interview

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:

  • Guidance of 15 days PTO annually

  • Stepful closed the last week of December

  • 15 work-from-anywhere days

  • 10 public holidays observed for 2026

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.

Stepful is proud to be an equal opportunity employer. We do not discriminate in hiring or any employment decision based on race, color, religion, national origin, age, sex, marital status, ancestry, disability, genetic information, veteran status, gender identity or expression, sexual orientation, pregnancy, or other applicable legally protected characteristic.