Learning Coach

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.

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

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 have

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