Learning Coach

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:

As a Learning Coach, you'll be the steady, proactive voice that keeps a cohort of Stepful students moving through their program — from their first week of class through graduation and into a healthcare job. You'll own a caseload of students end-to-end: tracking academic progress and payment status, spotting early warning signs, and building individualized plans to keep at-risk students on track.

Success in this role shows up in your cohort's engagement and completion rates — students who stay motivated, hit their milestones, and graduate ready to start their healthcare careers.

This is a fully remote, hourly contract (1099) position.

What you'll do:

• Student Coaching & Support
• Proactively reach out to your caseload of students via email, text, and phone to keep them engaged and on track
• Build individualized success plans for students flagged as at-risk, addressing academic, motivational, or personal barriers to completion
• Monitor each student's academic progress, attendance, and payment status throughout their program
• Case Management & Documentation
• Log every touchpoint in Stepful's coaching and CRM tools to maintain a clear, accurate record of each student's journey
• Keep student records current so anyone on the team can pick up a case with full context
• Cross-Functional Collaboration
• Partner with instructors and Stepful's Student Operations team to escalate at-risk cases and recurring blockers so issues get resolved quickly
• Share what you're seeing on the ground — what's helping students stay on track and what isn't — to help the Learning team keep improving the coaching model

What you'll bring:

• 1+ years of experience in student coaching, academic advising, career services, customer success, or another people-facing support role
• Comfort managing a high volume of outreach and follow-up across email, text, and phone
• Strong written and verbal communication skills, with the judgment to navigate sensitive or high-stakes conversations with care
• Highly organized, with the discipline to manage a full caseload of students without letting anyone fall through the cracks
• Comfortable learning new tools quickly, including CRM or case-management platforms

What you'll need:

• A reliable computer and high-speed internet connection
• A quiet, professional workspace for calls and video check-ins
• Availability during daytime hours, Monday - Friday 9am–7pm ET to align with student needs

Bonus points if:

• You've worked in healthcare, EdTech, or workforce-training environments
• You have experience supporting first-generation, career-changing, or historically underserved learners
• You've used tools like Front, HubSpot, or similar CRM/case-management platforms