[Hiring] Director of Operations @The Scholarship System

Role Description

Be the #2 person at a profitable, seven-figure online education company that has helped families win over $17.7 million in scholarships. You’ll run the business day to day with real authority, a profit share, and a founder who’s committed to staying out of your way, so she can teach and lead the vision, all while making a huge impact.

Full-time (W-2) · Remote (US) · Reports to the Founder/CEO · Starts December 2026 or January 2027

ARE YOU…

• The person who closes the loop: when you say it'll be done, it's done?
• Comfortable telling a teammate, kindly and directly, that a deadline slipped and what happens next?
• Happiest running a well-built system, and the first to notice when one needs updating or when something's missing?
• Ready to be the person a founder hands the keys to, so she can lead from the vision seat?

We'll be straight with you: this role has high expectations, and you'll have the authority and support to meet them. If that motivates you, keep reading.

Qualifications

• 3+ years running operations for a small team as an integrator, OBM, operations director or COO, ideally in online education, courses or memberships.
• Real online marketing experience: live launches, evergreen webinar funnels, and the numbers behind them (conversion rates, show-up rate, ROAS, cost per registrant).
• Lead magnets, sales pages, email sequences, webinars and Facebook ads should all feel familiar.
• You've run EOS/Traction or a similar meeting and planning rhythm.
• A people manager with a track record of accountability conversations.
• Strong in Asana and Notion, and comfortable using AI tools day to day.
• Detail-oriented about quality and brand, calm under tight deadlines, and a clear, concise writer.

Requirements

• Team rhythm and accountability: Run the weekly team meeting and quarterly planning (EOS/Traction).
• Launches and live webinars: Own the calendar and the plan for every launch.
• Retention: Own how many new members we keep, our biggest profit lever.
• Numbers and reporting: Know the key numbers every day, spot problems before Jocelyn even notices.
• People: Hire, onboard and coach the team, with clear roles, owners and backups.
• Systems and AI: Keep Asana, Notion, our SOPs and our AI tools current.

Benefits

• Base salary: $105,000–$115,000 (W-2), depending on experience.
• Annual bonus potential: $5,000–$20,000+, tied to your scorecard and a share of company profit above an annual baseline.
• On-target earnings: about $118,000–$128,000.
• Retirement: 401(k) with an employer contribution, eligible after one year.
• Growth budget for your own development: a coach, course or mastermind.
• Fully remote, with light Fridays (no standing meetings).
• Time off: 15 days of paid time off, 10 paid holidays, a paid week off between Christmas and New Year's, and your birthday off.
• Flexible hours, but reachable and responsive during the workday, roughly 9am–5pm Eastern.

How to Apply

Apply on this page with your resume, three short answers and a 3-minute video introduction. First round will involve a fast-paced Zoom call interview. Finalists complete a short paid test project. Lastly, there will be a longer interview with the final few candidates to ensure the right fit for both of us.

The Scholarship System is an equal opportunity employer. We welcome applicants of every background and make hiring decisions based on the role, the work and the person. If you need an accommodation during the hiring process, email [email protected]. Employment is at will, subject to applicable law.