Two Chicks With A Side Hustle

Help students from underserved communities succeed in allied healthcare training programs and launch meaningful careers—all from home.


About Stepful
Stepful is reimagining allied healthcare training with affordable, online, instructor-led, and AI-supported programs. We help learners—especially those from underserved communities—enter high-demand healthcare roles. Our graduates work for leading employers like CVS, NY-Presbyterian, and Walgreens. Backed by Y Combinator, Reach Capital, AlleyCorp, and a recent $31.5M Series B led by Oak HC/FT, Stepful was named the #1 EdTech company in the U.S. by TIME in 2025.

Our values:

  • Care first – We do whatever it takes for our students to succeed.
  • Learn quickly – We test, use data, and iterate.
  • Build together – We win when we rely on each other.
  • Own it – We take initiative and show pride in our work.

Schedule

  • Fully remote, contract role
  • Daytime hours, Monday–Friday (typically 8 AM–8 PM ET)
  • Compensation: $17–$18/hour

Responsibilities

  • Coach students who are struggling with motivation, grades, or program payments to help them stay on track to graduate
  • Provide timely, effective support to students using Front/HubSpot
  • Answer inbound calls from current and prospective students
  • Respond to email, SMS, and social media inquiries from potential students
  • Create and maintain help documentation for frequently asked questions
  • Work 1:1 with students to meet academic requirements for graduation

Requirements

Experience

  • 2+ years in career services or student coaching (preferred)
  • Experience with Front, Freshdesk, or HubSpot (preferred)

Skills & Knowledge

  • Excellent communication skills and strong attention to detail
  • Problem-solving skills to address issues and identify opportunities for improvement
  • Ability to manage multiple online tools and video-conferencing platforms

Other Requirements

  • Reliable computer and high-speed internet
  • Quiet, professional workspace

Benefits

  • Fully remote, flexible work environment
  • Opportunity to help students from underserved communities achieve career goals
  • Be part of a fast-growing, mission-driven EdTech company

If you’re passionate about student success and want to make a measurable impact, we’d love to hear from you.

Happy Hunting,
~Two Chicks…

APPLY HERE