Senior Software Engineer - AI

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.

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.

• 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.

• 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 piping large datasets through Large Language Models (LLMs).

• Proficiency in evaluating LLM performance, building robust testing frameworks, and iterating to improve model accuracy and efficiency.

• Familiarity with prompt-chaining, Retrieval-Augmented Generation (RAG), and other model optimization techniques.

• A relentless obsession with solving complex problems using cutting-edge technology and a strong commitment to continuous learning.

• Excitement about joining an early-stage company and a proactive, pioneering mindset for building new solutions from the ground up.

• A strong drive to make a tangible impact on people's lives through technology.

• Languages/Frameworks: Ruby on Rails, React, TypeScript

• Infra: Heroku, AWS, Vercel

• LLMs/AI: OpenAI, custom pipeline

• Data: Postgres, BigQuery

Compensation:

$140-200k base salary

Compensation for this role will fall within the pay range listed and will be determined based on job-related factors including, but not limited to, skills, experience, qualifications as well as interview evaluation. Ranges are market-dependent and may be modified in the future.

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.