Director of Student Success

Full-Time | Remote | Reports to Director of Student Success

We're scaling three programs simultaneously — SuperHuman, A2A, and our Uncommon Leaders Community — and the growth is real. This role exists to make sure our student success infrastructure grows with it. You're not here to manage support tickets or watch dashboards passively — you're here to build the systems that make them actionable, architect the strategy and the infrastructure that carry thousands of students from enrollment to transformation, and back again. You'll anticipate what's coming before it arrives and bring leadership the strategy to stay ahead of it. If you've scaled student success in online education, cohort-based learning, or professional development at scale, and you think in intelligent systems, this is your seat.

Profile insights

Here’s how the job qualifications align with your profile.

Skills

Do you have experience in Workforce management?

Location

Remote

Who We Are

The Uncommon Business is the world's fastest-growing AI-first education company, teaching business leaders to architect intelligent systems, not just prompt tools. We don't do busywork, legacy thinking, or 80-hour founder weeks. We build companies where AI handles the repeatable, humans drive the irreplaceable, and leaders scale without burning out. We're profitable, EOS-driven, and operate in championship-level surge cycles. You'll be promoted on impact and ownership — not tenure. High performers thrive here. Passengers don't last.

If You Worked Here Last Week

You might have:

  • Spotted a bottleneck in the student engagement process, scoped the fix, and handed it to the team to execute — response time improved within a week

  • Designed a UCL retention strategy for the next growth phase that preserves the community's intimacy as membership doubles

  • Identified a 12% drop in Superhuman completion rates, traced it to a specific module, and had a fix in front of the curriculum team within 48 hours

  • Mapped the full student lifecycle across all three programs and identified the top three drop-off points driving re-enrollment gaps — with a 90-day fix plan

  • Created a quarterly student success report for leadership that connects outcomes data to revenue — completion rates to re-enrollment to LTV

Your Core Responsibilities

We value ownership over task lists. Here's where you'll lead:

Cross-Program Student Success Strategy: Own the strategic success roadmap across A2A, Superhuman, and Uncommon Leaders Community — each with distinct volume, intensity, and success definitions. Own and optimize the full student journey from purchase to first win, ensuring every student has a clear path from enrollment to measurable transformation.

AI-First Infrastructure for Scale: Build the CS infrastructure before we need it — intelligent onboarding flows, automated engagement triggers, predictive churn signals, and feedback loops that scale to thousands of students without proportional headcount growth.

Risk Intelligence & Leadership Reporting: Own all leading indicators — NPS, activation rates, completion rates, community engagement — and surface risks with proposed solutions before they escalate, never after.

Team Leadership: Directly manage Student Success team, set the strategic direction the team executes against, and scale the team as volume demands.

UCL Community Experience at Scale: Own the strategy for how Uncommon Leaders maintains its premium, high-touch feel as the community grows — defining what a thriving member looks like at every stage and building the systems to get them there.

The Traits We’re Calling In

We hire humans, not checklists, but success here requires:

  • You've led student success at an education company or learning institution serving thousands of students simultaneously — you know what breaks at scale before it breaks

  • You default to AI-first solutions, architecting intelligent workflows and automations rather than adding headcount, and you have a clear point of view on where AI should and shouldn't replace the human touch

  • You think in systems and bring data to every conversation — NPS drops, completion gaps, and engagement trends are puzzles you solve, not metrics you report

  • You're proactive by default — you don't wait to be asked, you come to leadership with the problem and the solution already framed

  • You thrive in fast-moving, still-being-built environments where your fingerprints end up on the infrastructure everyone else relies on

What Success Looks Like

You own these key metrics:

  • NPS: 70+ maintained across all three programs at all times

  • Completion & Activation: 80%+ of enrolled students activate and complete core curriculum milestones

  • Community Engagement (UCL): 60%+ member participation on weekly touchpoints

  • Infrastructure Readiness: SS systems fully built and documented for 5,000+ student scale before we hit that number

  • Risk Management: Zero leadership surprises on student success — all risks surfaced proactively with proposed solutions

📋 Launch Season Expectations

Our launch seasons are intentionally high-intensity and fast-paced to drive transformation for our clients and our team. Twice per year (10–12 weeks total), team members in launch-critical roles are expected to be available from 7 AM to 7 PM, with additional hours often required for preparation, execution, live event support, and post-launch debriefs.

This pace is not for everyone — and that's okay. We set this expectation clearly so that only those who thrive in high-accountability, high-impact environments choose to be here. Outside launch seasons, workload is sustainable and strategic — focused on building the systems that make the next launch even stronger.

💰 COMPENSATION & BENEFITS

  • Base Salary: $95,000–$125,000

  • Performance Bonus: Tied to NPS, completion, and retention KPIs

  • Structure: Direct W-2 hire

We Invest in Your Performance, Not Just Perks

  • Health & Wellness: Monthly wellness stipend + access to personalized and group wellness coaching to sustain high performance

  • Professional Growth: $1,500–$3,000 annual development budget for courses, conferences, certifications, and tools that sharpen your edge

  • Work Your Way: Coworking membership allowance OR home office setup budget — you choose what maximizes your focus

  • Unlimited PTO: Real flexibility with clear boundaries — we operate in championship seasons (launch intensity) and strategic recovery periods

  • Full Remote Setup: MacBook, external monitor, desk equipment — we equip you to do your best work

  • True Downtime: Company-wide closure December 25–January 1 so you can fully disconnect

Apply Now

The Uncommon Business

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