Director of Operations - Remote, Online Education

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?
- Energized by people: you'd rather check in with the team than work in a silo?
- 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.

ABOUT THE SCHOLARSHIP SYSTEM
We help families pay for college with as little student debt as possible. Jocelyn Pearson (Founder/CEO) graduated debt-free on six figures in scholarships, wrote The Scholarship System in 2014, and has run the company full-time since 2015. TSS families have now won over $17.7 million in scholarships. We're a small, remote, seven-figure education business: a membership, a cohort bootcamp, live webinars and an evergreen funnel. Our values are impact, innovation, resourcefulness and compassion.

The systems are built. Notion, Asana, Circle and Claude run the business. What we need is the leader who runs the team on them, and keeps them current as we grow, so launches ship on time and the founder isn't the one checking.

WHY YOU'LL LOVE IT HERE
- You're the #2, not three layers down. You work directly with the founder, Jocelyn, and what you build gets seen and used right away.
- Real authority. You get written decision limits, you break ties, and the founder commits not to go around you.
- When the company wins, you win. You share in company profit above an annual baseline, on top of your salary.
- The systems are mostly built. You get to run something good, fine-tune it to be better, not rescue a mess.
- We practice what we teach. We help families work smarter, and we run the company that way: light Fridays, a paid winter break, and no rewards for burnout.
- Work you can feel good about. Every launch you run helps a family pay for college with less debt.

WHAT YOU'LL OWN
You are in the business so Jocelyn can work on the business. You protect the founder's time as the Business "Integrator" per the EOS methodology. You'll lead a remote team of 6–8: marketing tech, customer success, community, content and video, plus partners for paid ads, web and a fractional CMO.

- Team rhythm and accountability. Run the weekly team meeting and quarterly planning (EOS/Traction). Know where every person's goals and tasks stand, follow up until loops close, and have the direct conversation when something slips.
- Launches and live webinars. Own the calendar and the plan for every launch, and run them from templates. You own the quality bar before anything goes live: you make sure every page, form, email and automation is tested against our QA checklist, and you give the final sign-off that the work is on brand.
- 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, and send her a short written report every Monday, so she never has to ask for status.
- People. Hire, onboard and coach the team, with clear roles, owners and backups. Your first hire will likely be our social media lead. You're the go-to when a teammate is stuck: you unblock them quickly and coach them to solve it on their own next time.
- Systems and AI. Keep Asana, Notion, our SOPs and our AI tools current. Lead our AI innovation by pulling only the most immediate levers that make the biggest difference, so the team stays focused. You maintain and prioritize, and you spot the gaps that need filling or the updates that need to be made.

HOW WE'LL WORK TOGETHER
- You run the meetings; Jocelyn gets the report.
- You work from the annual calendar and look 3–5 months around the corner. You plan the team's capacity, so everyone knows what they own for the next 90 days. You prevent scramble.
- Make the decisions inside your limits without escalating. On the rest, bring "here's the plan," not "what do you think?", and hold the team to the same standard to reduce distractions. On day-to-day calls, you break ties.
- New ideas go to a holding pen, not straight into the plan. If something is added, something comes off.
- In return, Jocelyn commits to a weekly 1:1, a monthly planning session with just the two of you, answers within 24 hours, and no going around you with the team.

A TYPICAL WEEK
Every week changes, especially in launch season, but here's the rhythm. Every day starts with the numbers and the team's status. This role context-switches all day; it isn't heads-down solo work.
- Monday: Send the CEO report. Run the team meeting and any department breakouts. Turn decisions into owned, dated tasks.
- Tuesday: Launch and project work: plans, kickoffs, checking what's due this week. Follow up on anything at risk.
- Wednesday: 1:1 with Jocelyn: dashboard first, then decisions. 1:1s or check-ins with team members.
- Thursday: Review the week's status and numbers. Have any accountability conversations. Clear red tasks.
- Friday: A lighter day with no standing meetings: look 3–5 months ahead on the annual calendar, update the dashboard and prep next week.
- Launch weeks: Daily numbers check, reallocating coverage, and final checks before anything goes live.

YOUR FIRST 90 DAYS
We care most about three things: launches that ship on time without Jocelyn, how many members we keep, and profit. Specific baselines and targets are shared during the offer process.

By early March, Jocelyn delivers the bootcamp's live trainings and nothing else, and the launch still runs on time and meets its goals. You'll also know it's working when:
- A Monday report arrives every week, and Jocelyn hasn't had to ask anyone for status in a month.
- There are no overdue tasks across the team.
- You've run quarterly planning and owned a launch end to end.

- 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.

Nice to have: experience with Circle, ActiveCampaign, WebinarJam/Everwebinar, SamCart.

This probably isn't the role for you if you'd rather be the visionary or build your own brand on the side, or if conflict and hard feedback drain you.

- 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). Expect some evenings and weekends around launches and live webinars.
- This role does not include health insurance.
- 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. Time off is planned around our launch calendar: no PTO during the two weeks before and during our bootcamps or Black Friday week.
- Flexible hours, but reachable and responsive during the workday, roughly 9am–5pm Eastern.

Final bonus structure and targets are confirmed at the offer stage.

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 hidden]. Employment is at will, subject to applicable law.