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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.

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.

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.

Success in this role is measured by:

1. Member Response Time — Median first response to community posts/DMs within 1 business day; same-day response on weekdays for time-sensitive questions.
2. Essay & Application Reviews (Shared) — Provide scholarship essay and application reviews on an as-needed basis, splitting them with our other primary reviewer.
3. Live Q&A Cadence & Attendance — Hosting scheduled live Q&As (weekly or bi-monthly as assigned) with attendance and replay engagement above agreed benchmarks.
4. 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).
5. Scholarship & Debt-Free Wins — Number of documented student wins (scholarships awarded, debt-free graduations, appeal successes) attributed in part to coaching/community support.
6. Testimonials Captured — Target of 2-5 usable written/video testimonials surfaced and routed to the marketing team each month.
7. Retention & Satisfaction — Course/community retention rate and member satisfaction scores.
8. Feedback Loop Quality — Consistent weekly reporting of member sentiment, recurring questions, and content/tool improvement ideas to the leadership team.
9. 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.
10. Member Retention Rate — % of trial completions and reduced refund rate

• $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.

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.

Requirements

Qualified candidates have:

• 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 — whether as a recent successful TSS/DFD Lab member, a parent who recently navigated paying for college, or a professional in high school or college world. You don't need to be a credentialed industry professional.
• Working familiarity with FAFSA, scholarship essays, and the U.S. college funding landscape — enough to coach members, with willingness to deepen your expertise inside our system.
• 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).
• Reliable daily availability during U.S. business hours.

Nice-to-haves:

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

Skills and Abilities

You are a strong fit for this position if the statements below are true for you:

• You fully embrace technology and dive into any opportunity to learn new systems and ways of doing things.
• You delight in the details and you don’t let little things slip through the cracks.
• You would never utter the words “That’s not my job” – instead you always jump in to help
• Your past employers would call you a natural go-getter. If you can do better work, you will always rise to the challenge.
• You are inherently compassionate and believe that most people are doing the very best they can.
• You are comfortable speaking with customers whether via a phone or Zoom call
• You enjoy writing, proofreading or anything essay-related
  

Benefits

Great Reasons to join The Scholarship System include:

• 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. Need to pick up the kids? Groceries? Spa afternoon? No worries. You can choose your hours - we just need the work done.
• Opportunities for growing your personal skills, knowledge and competencies as we stay ahead of trends and are constantly iterating and growing, including with AI
• 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!