Director Learning Technology Jobs in Rye, NY (NOW HIRING)

Stepful is reimagining allied healthcare training by offering affordable, online, instructor-led, and AI-supported programs that help learners 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.

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.

We’re improving access to quality healthcare for everyone, everywhere, and improving access to healthcare careers for those who need them most.

As our Head of Learning, you will define and execute Stepful’s learning strategy across a growing portfolio of healthcare programs. You will own the quality and effectiveness of our learning experience, from curriculum development, instructional delivery, on-the-ground clinical rotation design, to student outcomes and continuous improvement.

You will lead a team of curriculum developers, instructional designers, and subject matter experts and work closely with Product, Operations, Compliance, and healthcare partners. This role is ideal for a hands-on learning leader who can set a clear vision, build scalable systems, and use data to improve outcomes for students.

This role reports into our SVP, Learning and Operations.

• Learning vision and strategy: Define the vision and strategy for Stepful’s learning offering based on student needs, business priorities, and healthcare workforce demand.

• Program and content roadmap: Develop and own the roadmap for new programs, curriculum improvements, assessments, and learning modalities.

• Program development: Lead the end-to-end development and launch of high-quality online and blended healthcare programs.

• Learning operations: Build repeatable processes to develop, maintain, and improve curriculum efficiently across a growing portfolio of programs.

• Learning innovation: Develop new learning modalities and apply AI and emerging technologies to personalize learning, improve engagement, and strengthen skill development.

• Industry alignment: Build strong relationships with healthcare employers, academic experts, and industry organizations to understand emerging learning and workforce needs.

• Cross-functional collaboration: Partner closely with Operations, Compliance, and Workforce Solutions to incorporate student and instructor feedback and shape the broader learning experience.

• 10+ years of experience in online or blended learning, curriculum development, academic program management, instructional design, or education operations.

• Experience in healthcare education, EdTech, or workforce development.

• Experience managing curriculum developers, instructional designers, subject matter experts, or other learning teams.

• Highly analytical mindset, using data to improve learning experiences and student outcomes.

• Ability to translate complex healthcare or technical subject matter into clear and effective learning experiences.

• Strong communication and cross-functional collaborative skills

• Ability to thrive in a fast-paced, ambiguous environment.

• Passion for helping students change their lives through access to education.

• You have clinical experience or have designed learning experiences and curriculum in a healthcare setting

• Introductory call with Talent Acquisition team member

• Interview with Hiring Manager

• Take-Home Assignment

• Virtual Panel Interview

• On-Site Panel Interview

• 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 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.