Senior Software Engineer - AI

About Stepful:

At Stepful, we’re on a mission to reimagine allied healthcare training by providing affordable, online, instructor-led and AI-enabled education to help learners - especially from underserved communities - launch high-demand healthcare careers on their own terms. In addition to our direct-to-consumer training model, Stepful partners with healthcare institutions to build talent pipelines and career pathways in an effort to mitigate the increasing allied health employee shortage. Our graduates - inclusive of Medical Assistants, Pharmacy Technicians and more - go on to work for leading institutions such as CVS, NY-Presbyterian and Walgreens.

Stepful is backed by Y Combinator, Reach Capital and AlleyCorp, and we recently closed a $31.5M Series B round led by Oak HC/FT. Additionally, TIME named Stepful the #1 EdTech company in the U.S. for 2025.

Stepful unlocks the full potential of the global workforce, improving access to quality healthcare for everyone, everywhere.

Our values:

At Stepful, we attribute much of our success to the high caliber of our team. To that end, we seek to onboard mission-driven individuals who thrive in a fast-paced environment, don’t shy away from ambiguity and demonstrate our four company 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:

This is a unique opportunity for a Product Engineer on our AI Team to shape the future of education and career advancement at Stepful. You'll be at the forefront of integrating cutting-edge AI into our core products, directly impacting the learning journey and career outcomes of thousands of students from underserved communities. You will build innovative solutions that enhance the student experience, empower our internal teams, and drive the creation of dynamic, adaptive educational content. Success in this role will be measured by student satisfaction and increasing operator/employee efficiency–letting operators focus on substantive human interaction. The work style will include R&Ding new tools and building 0-to-1 experimental products. This is a hybrid opportunity with our team in-office Tuesday through Thursday in our Soho office. This role reports to our Founding Engineer/Engineering Manager.

What you’ll do:

• World-Class Learning Experience Development:

  • Develop and iterate on our advanced Learning Management System (LMS) with a focus on seamless user experience (UX), adaptive learning pathways, peer-to-peer engagement, gamification, and motivational mechanisms to ensure impactful outcomes for students.

• Innovative Career Services with Generative AI:

  • Apply Generative AI techniques to enhance the job-seeking process for our graduates, from automated resume generation to personalized interview training tools.

  • Work closely with the Career Services team to understand needs and implement features that empower graduates to secure high-demand healthcare careers.

• Internal Workforce Empowerment:

  • Design, build, and maintain robust platforms and tools for instructors, TAs, coaches, and operators, leveraging Generative AI to optimize student success and operational efficiency.

  • Collaborate with various internal teams to identify pain points and develop AI-driven solutions that maximize their impact on students' lives.

• Cutting-Edge Content Management & Generation:

  • Develop technology to generate, maintain, and adapt educational content at scale, significantly reducing curriculum creation time and enabling rapid iteration based on learning needs.

  • Explore and implement advanced techniques for automated content generation and personalized learning pathways.

• Reliable Data Pipelines:

  • Ensure data reliability and accessibility across Stepful, building robust data pipelines that empower business, learning, and operations teams to make informed, data-driven decisions.

  • Own Stepful’s prompt chaining and context retrieval pipelines, and evaluate prompt success with A/B testing.

What you’ll bring:

• 6+ years of engineering experience, with a strong preference for backgrounds in direct-to-consumer startup environments.

• 2+ years of hands-on experience building and launching Generative AI products.

• Deep experience with Ruby on Rails, React, TypeScript, Node.js.

• Demonstrated experience handling and