[Hiring] Virtual Assistant - Customer Success Manager and Content Expert @The Scholarship System

Role Description

The role of the Customer Success Manager & Content Expert exists to make every TSS student and parent feel supported, seen, and successful — and to drive real, measurable scholarship and debt-free outcomes. You'll be the day-to-day face of TSS inside our community and app, combining deep subject-matter expertise in scholarships and financial aid with strong community management, member support, and content engagement skills. Your work directly fuels member results, retention, testimonials, and referrals.

Success in this role looks like:

• Fast, warm member response times across our community within Circle, social media, and Helpscout
• A healthy, engaged community (active members, post engagement, new-member activation)
• Documented scholarship and debt-free wins tied to your coaching and support
• A steady flow of testimonials captured and routed to marketing
• Strong course/community retention and member satisfaction
• A consistent weekly feedback loop to the leadership team
• 1–2 member-experience improvements shipped per month
• A measurable save rate on at-risk members
• Reduced refund rate due to improved member retention

Qualifications

• 20 hours of consistent weekly availability overlapping 9-3ET for at least a few hours per day
• Firsthand experience with scholarships and the college financial process
• Working familiarity with FAFSA, scholarship essays, and the U.S. college funding landscape
• Experience in customer support, community management, or coaching in an online environment
• Excellent written communication — clear, warm, on-brand, with strong grammar
• Comfort hosting live video calls on occasion
• Tech-savvy and willing to learn new platforms (Circle, Google Suite, Notion, AI tools)

Requirements

• Prior participation in The Scholarship System course or Debt-Free Degree Lab (nice-to-have)
• Experience with Circle, ActiveCampaign, SamCart, Help Scout, and Asana (nice-to-have)
• Experience supporting online course launches and webinar funnels (nice-to-have)

Benefits

• Amazing team - be welcomed to a small group who truly cares about each other & has fun even though we're remote
• Work from home – this is a fully remote position
• Reliable work from a consistent employer
• Flexible work hours - while you must work each day, we do not require you to work specific hours/time frames
• Opportunities for growing your personal skills, knowledge and competencies
• A culture that emphasizes respect for every individual
• Company commitment to work/family life balance
• Knowing every day you are helping families work towards a debt-free education
• Company year-end bonuses
• Company live launch bonuses and other little gifts and surprises
• If you have teens or college-aged students, access to our materials and trainings to pursue a debt-free degree
• Interested in a course or training program? If it will benefit you in your role, we are open to paying for it!