Virtual Assistant - Customer Success Manager and Content Expert

About The Scholarship System The Scholarship System (TSS) is an online education company on a mission to help families graduate from college debt-free. Through our flagship course, The Scholarship System , and our Debt-Free Degree Lab (DFD Lab) membership — now unified in our new TSS mobile app — we equip students and parents with the strategies, tools, software solutions, and community support they need to win scholarships, navigate financial aid, and make smart college decisions without taking on crushing debt. We are a small, fully remote team that uses modern tools and AI heavily (Notion, Circle, Claude, ChatGPT, and our own Tess Tools). Our community uses the language of "Rebel Families" — families who refuse to accept that crushing student debt is normal. Role Overview 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 Specific numeric targets will be set with your manager during onboarding and reviewed weekly and quarterly. What You'll Do Community & Member Support Welcome new members, moderate Circle community posts, and protect a healthy, encouraging culture. Respond to member questions, DMs, and comments daily across Circle and Helpscout . Handle cancellations and refunds in Helpscout and SamCart — apply retention scripts, document reasons, and surface trends to the team. Publish recurring touchpoints: Scholarship Sunday , Monthly Wins , accountability posts, and weekly superstar shout-outs. Manage Circle access groups and basic community ops. Scholarship & Financial Aid Coaching Host live member sessions: Strategy Sessions (occasional) and monthly RebelFamily Rally (we rotate so this ends up 4-5 times per year) Review scholarship essays and applications with strategic, actionable feedback (backup/overflow coverage). Coach members through paying-for-college topics through community replies, email support, and the periodic Q&A hosting. We provide training on many topics but experience even at a personal level with the US college system, including scholarships and FAFSA, is necessary. Maintain the DFD Lab Monthly Guide and Seasonal Scholarship Lists . Plan and run our Annual Scholarship program. Content Engagement & Feedback Loop Draft YouTube scripts and member/non-member newsletters using our playbook, then review for accuracy, tone, and brand voice before hand-off. Fact-check blog posts for FAFSA, scholarship, and financial-aid accuracy before publish. Respond to YouTube, Facebook, and Instagram comments as our subject-matter voice. Review the member feedback survey consistently and report sentiment, recurring questions, and content gaps with actionable solutions where possible. Pull weekly customer and employee headlines for marketing. Proactively request official testimonials from members after wins and milestones using approved templates; collect written and/or video testimonials and capture proper release/permission. Log testimonials in Notion and route the best to marketing. Provide subject-matter expert input on course updates and revisions, typically annually and as-needed. Member Experience & Retention Own the question "How can we serve our members better?" — audit the end-to-end member journey quarterly and test 1–2 improvements per month. Identify and run save-the-member outreach to at-risk members (low engagement, missed calls, unanswered questions). Run small experiments on activation, engagement, and retention; measure and iterate. Operations & Launch Support Review/approve affiliate applications, respond to partnership/HARO requests, and process monthly affiliate payouts . Support the CEO with podcast interviews — coordinate scheduling, prep guest research and talking points, manage day-of logistics, and handle follow-up communications. Log reported scholarship wins to our wins spreadsheet. Update the DFD Retention Calculator monthly. Contribute extra hours during launches (2–3 times/year) for webinars, bootcamps, and onboarding waves, supporting the CEO on chat and Helpscout. Key Performance Indicators (KPIs) Success in this role is measured by: Member Response Time — Median first response to community posts/DMs within 1 business day; same-day response on weekdays for time-sensitive questions. Essay & Application Reviews (Shared) — Provide scholarship essay and application reviews on an as-needed basis, splitting them with our other primary reviewer. Live Q&A Cadence & Attendance — Hosting scheduled live Q&As (weekly or bi-monthly as assigned) with attendance and replay engagement above agreed benchmarks. Community Health — Weekly active members, post engagement rate, and new-member activation rate (% of new members who post or comment within their first 14 days). Scholarship & Debt-Free Wins — Number of documented student wins (scholarships awarded, debt-free graduations, appeal successes) attributed in part to coaching/community support. Testimonials Captured — Target of 2-5 usable written/video testimonials surfaced and routed to the marketing team each month. Retention & Satisfaction — Course/community retention rate and member satisfaction scores. Feedback Loop Quality — Consistent weekly reporting of member sentiment, recurring questions, and content/tool improvement ideas to the leadership team. Member Experience Improvements Shipped — 1–2 proposed and implemented improvements to the member journey per month (new touchpoint, process change, content fix, retention experiment, etc.), with measurable impact tracked over time. Member Retention Rate — % of trial completions and reduced refund rate Compensation $1,750–$3,000/month (~$21–36K/year) for an expected ~20 hours/week as a 1099 independent contractor. Equivalent to $20–$35/hour , depending on experience, scholarship subject-matter depth, and AI fluency. Quarterly and annual performance bonuses tied to retention, activation, and member wins. Pay reviewed at 90 days and annually; room to grow scope and rate for top performers who consistently hit outcome targets. How to Apply Submit your application through Workable with your resume, DISC results (PDF), and answers to the questions through the form. Strong candidates will be invited to a short intro call, followed by a trial assignment (e.g., reviewing a sample scholarship essay and drafting a community welcome post) before a final interview.