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 Legal Operations Associate to support our Legal, Compliance & Public Affairs team as we scale. As Stepful grows, so does the complexity of our regulatory environment — we manage relationships with state authorizers, accreditors, and boards of nursing across multiple jurisdictions, and compliance is a core strategic asset for the business.

In this operational support role, you'll own reporting deadlines and submissions, maintain licensing and instructor registrations, support cross-functional compliance initiatives, and help build and improve the internal processes and tools that keep the team running efficiently. It's a role where attention to detail and a knack for process improvement have a direct impact on a fast-growing company navigating an increasingly complex regulatory landscape.

This hybrid role (3 days/week in office) reports to the Director of Compliance & Public Policy.

What you’ll do:

• Ongoing trade school reports, renewals, and submissions (estimated 3-5 per month of varying degrees of complexity)

• Complete trade school licenses in outstanding jurisdictions

• Maintain instructor and agent registration across licensed jurisdictions

• Creation of internal resources to support cross functional teams

• Develop use cases for AI in areas such as compliance monitoring, research, and workflow automation. Critically assess the risks, benefits, and ethical considerations of applying AI within a regulatory compliance context to ensure responsible and effective deployment.

• Manage and support key projects across Stepful, collaborating with cross-functional team members at all levels to execute Legal Compliance & Public Affairs-driven initiatives efficiently

• Create and maintain robust information management processes for the storage of critical Legal Compliance & Public Affairs documents, including state licenses, corporate governance materials, policies, and project tracking information. You will ensure that our Legal Compliance & Public Affairs information is organized, accessible, and compliant.

• Drive the adoption and optimization of tools to deliver meaningful improvements and measurable efficiencies for the Legal Compliance & Public Affairs team

What you’ll bring:

• You should possess a minimum of 5 years of experience in a similar role (legal ops experience, paralegal experience, or project management experience), with demonstrated success in driving technology-led projects for a legal/compliance department

• Experience project managing initiatives in a fast-paced environment with a variety of business stakeholders

• Excellent communication, analytical and writing skills across a variety of stakeholders, with the ability to present information clearly and concisely to different audiences

• Strategic thinker with the ability to think holistically while focusing on day-to-day project management and driving results

Interview Process:

• Introductory call with a Talent Acquisition team member

• Interview with Hiring Manager

• Take-Home Assignment

• Virtual Panel 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 $80,000 - $100,000, 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.