Head of Learning

About Stepful

Stepful is working to make allied healthcare training more accessible by delivering low-cost, online, instructor-led, and AI-enabled programs that help people from all backgrounds begin careers in high-demand healthcare roles.

Alongside its direct-to-consumer training, Stepful collaborates with major healthcare organizations to help close the nationwide shortage of healthcare workers. Its alumni, including Medical Assistants, Pharmacy Technicians, Nurses, and others, feed talent pipelines for employers such as CVS, NY-Presbyterian, HCA, Providence, and Walgreens.

The company is supported by Y Combinator, Reach Capital, and AlleyCorp, and recently completed a $55M Series C round led by Oak HC/FT. TIME recognized Stepful as the #1 EdTech company in the United States for 2025.

Stepful’s mission is to expand access to quality healthcare for everyone, everywhere, and to open up healthcare career paths for the people who need them most.

Values

The team credits its progress to a strong, mission-driven culture. Stepful looks for people who do well in fast-moving, uncertain environments and who live its four core values:

• Care first: do everything possible to help students succeed.
• Learn quickly: test ideas, use data, and keep improving.
• Build together: succeed through close collaboration.
• Own it: take initiative, act responsibly, and take pride in the work.

Role overview

As Head of Learning, you will set and drive Stepful’s learning strategy across an expanding set of healthcare programs. You will be accountable for the quality and impact of the learning experience, covering curriculum creation, instructional delivery, clinical rotation design, student outcomes, and ongoing refinement.

You will manage a team of curriculum developers, instructional designers, and subject matter experts, while partnering with Product, Operations, Compliance, and healthcare partners. This is a hands-on leadership role for someone who can establish a clear direction, create scalable operating systems, and use data to continuously improve learner outcomes. The position reports to the SVP, Learning and Operations.

Key responsibilities

• Set the learning vision and long-term strategy based on student needs, company priorities, and healthcare workforce demand.
• Own the roadmap for new programs, curriculum enhancements, assessments, and learning formats.
• Lead the full lifecycle of building and launching strong online and blended healthcare programs.
• Create repeatable systems that make curriculum development, upkeep, and improvement more efficient across multiple programs.
• Introduce new learning approaches and use AI and emerging technologies to personalize learning, increase engagement, and strengthen skill growth.
• Develop relationships with healthcare employers, academic specialists, and industry groups to stay aligned with evolving workforce and learning needs.
• Work closely with Operations, Compliance, and Workforce Solutions to integrate feedback from students and instructors and improve the overall learning experience.

Requirements

• At least 10 years of experience in online or blended learning, curriculum development, academic program management, instructional design, or education operations.
• Background in healthcare education, EdTech, or workforce development.
• Prior experience leading curriculum developers, instructional designers, subject matter experts, or similar learning teams.
• Strong analytical ability with a habit of using data to improve learning design and student outcomes.
• Ability to simplify complex healthcare or technical topics into effective learning experiences.
• Excellent communication skills and the ability to collaborate across functions.
• Comfort working in a fast-paced environment with ambiguity and change.
• Genuine interest in helping students transform their lives through education.

Preferred background

Clinical experience, or prior work designing curriculum and learning experiences in a healthcare setting, is a plus.

Interview process

• Introductory conversation with a Talent Acquisition team member.
• Interview with the hiring manager.
• Take-home assignment.
• Virtual panel interview.
• On-site panel interview.

Benefits and compensation

• Meaningful equity stake.
• Subsidized medical, dental, and vision insurance options.
• 401(k) plan.
• FSA, HSA, and commuter benefits.
• Learning stipend.
• Open vacation policy.
• Guidance of 15 days of PTO per year.
• Company closure during the last week of December.
• 15 work-from-anywhere days.
• 10 public holidays observed for 2026.

Compensation note

The base salary is intended to be part of a competitive total rewards package that also includes equity and benefits. Actual pay may differ from the target range depending on experience, internal pay equity, and other relevant business factors.

Equal opportunity

Stepful is an equal opportunity employer and makes hiring decisions without regard to race, color, religion, national origin, age, sex, marital status, ancestry, disability, genetic information, veteran status, gender identity or expression, sexual orientation, pregnancy, or any other legally protected characteristic.