Learning Coach

Stepful • New York, NY

10d • $18 - $20 • Remote

About The Position

Stepful is a workforce platform that helps America's largest health systems build, train, and retain their talent. Since its founding in 2021, Stepful has trained over 32,000 practice-ready healthcare workers. The company partners with leading healthcare institutions to address the national shortage of healthcare workers, aiming to improve access to quality healthcare and healthcare career ladders. Stepful's students form talent pipelines for major employers like NY-Presbyterian, Mt. Sinai, HCA, Providence, CVS, and Walgreens, with partnerships across half of the top 10 health systems in the US. The company is backed by Y Combinator, Reach Capital, and AlleyCorp, with a recent $55M Series C led by Oak HC/FT, and was named the #1 EdTech company in the U.S. by TIME for 2025. Stepful values mission-driven builders who thrive in fast-paced, ambiguous environments and embody their core values: Care first, Learn quickly, Build together, and Own it.

Requirements

• 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.
• 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.

Nice To Haves

• Worked in healthcare, EdTech, or workforce-training environments.
• Experience supporting first-generation, career-changing, or historically underserved learners.
• Used tools like Front, HubSpot, or similar CRM/case-management platforms.

Responsibilities

• 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.
• 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.
• 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.

Benefits

• The target hourly rate for this opportunity is $18/hour - $20/hour.
• This is a 1099 independent contractor position; individual pay may vary based on experience, internal pay equity, and other relevant factors.
• This role is not benefits-eligible.

What This Job Offers

• Career Level: Entry Level
• Education Level: No Education Listed