Associate Director, People Operations

About Stepful:

Stepful is reimagining allied healthcare training by offering affordable, online, instructor-led, and AI-supported programs that help learners—especially those from underserved communities—launch high-demand healthcare careers.

In addition to our direct-to-consumer training, Stepful partners with leading healthcare institutions to build talent pipelines and address the growing shortage of allied health workers. Our graduates, including Medical Assistants, Pharmacy Technicians and more, go on to work at major employers like CVS, NY-Presbyterian, and Walgreens.

Stepful is backed by Y Combinator, Reach Capital, and AlleyCorp, with a recent $31.5M Series B led by Oak HC/FT. We were named the #1 EdTech company in the U.S. by TIME for 2025.

We’re unlocking the full potential of the global workforce—improving access to quality healthcare for everyone, everywhere.

Our values:

We credit much of our success to our exceptional team. We’re looking for mission-driven individuals who thrive in fast-paced, sometimes 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:

We’re hiring an Associate Director, People Ops and Programs to operate in a founding People Operations role, reporting to the VP of People. You will own People Ops programs end-to-end—strategy, design, rollout, enablement, measurement, iteration. You will build our core People Ops systems (HRIS, performance/engagement platforms, LMS) and launch reliable workflows and operations to support an employee base that will grow to 150+ over the next 12 months with hundreds of contractors. You will also partner with leaders on complex people issues—providing coaching, clear recommendations, and structured documentation. This role will grow into a player-coach position as we scale, with the opportunity to build and lead a small Programs/Ops team.

Location: Hybrid — Tue–Thu in our SoHo HQ (408 Broadway, NYC).

What you’ll do:

Own People Ops programs

• Set strategy, design programs, run launches, enable managers, measure outcomes, and iterate quickly.

• Ship clear cadences, playbooks, templates, and KPIs for onboarding, performance, engagement, and manager enablement.
  

Systems, tooling, and operations

• Own HRIS, performance/engagement platforms, and LMS; design and maintain integrations.

• Build automated flows for the employee lifecycle across diverse employee populations (FTE, Contractor, Hybrid, Remote)

• Evaluate and implement new tools with clear ROI and adoption plans.
  

People Partnership

• Coach managers on feedback, performance expectations, team dynamics, and change.

• Lead low-to-moderate complexity ER matters; escalate high-risk cases with Legal and the VP of People.

• Provide timely, documented recommendations with clear business impact; maintain consistent ER records.
  

Process, policy, and compliance

• Keep core processes tight: offboarding, I-9/E-Verify, leaves, multi-state compliance, documentation.

• Refresh policies with Legal/Compliance and Workplace/IT to reinforce a high-performance, inclusive culture.
  

Cross-functional collaboration

• Partner with Finance, Legal/Compliance, IT, Recruiting to scale reliable, repeatable processes.
  

What you’ll bring:

• 6+ years in People Operations/Program Management, with a record of shipping company-wide programs and improving them with data.

• Hands-on experience running onboarding and performance cycles in high-growth or dynamic environments.

• Systems mindset: you’ve administered HRIS platforms, built integrations, and automated workflows.

• Strong analytical skills; you build dashboards and drive decisions from metrics.

• Practical knowledge of multi-state compliance and sound judgment on sensitive people issues.

• Clear communicator, low-ego collaborator, bias for action.
  

Bonus points if:

• Built programs 0→1 at a startup

Interview Process:

• Intro call with Talent Acquisition

• Interview with the VP of People

• Take-home exercise

• Virtual panel with cross-functional partners

• On-site panel in NYC and final conversation with a founder

Benefits and Compensation:

• Meaningful Equity Stake

• Subsidized Medical, Dental, and Vision insurance plan options

• 401(k)

• FSA, HSA and commuter benefits

• 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 2025

The target base salary range for this opportunity is $160,000 - $185,000, 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.

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.