Help us get more students from sign-up to success.
Student Success Agency is looking for a data-obsessed, mission-driven leader to own student engagement across the Winbox platform — the tool thousands of students use to access mentors, tutors, and guidance that changes their lives.
As Seen In & Recognized By
The Mission
Engagement that changes student outcomes.
Student Success Agency serves thousands of students across the country through partnerships with school districts. But our mission is bigger than sign-ups.
We built the Winbox — a platform that connects students with mentors, tutors, and college guidance. The hard part isn't getting students to sign up. It's getting them to come back, take action, and build the habits that change their trajectory.
That's where you come in.
Students Served
Thousands across the US
Platform
The Winbox — mentors, tutors, guidance
Your Impact
Student engagement & retention metrics
Team You'll Lead
Agent Success, Specialist Services, Student Safety
See Us in Action
Hear our story
Get a feel for who we are, what we're building, and why it matters.
The Role
What you'll own
This is a builder role. You'll set strategy, run experiments, and own the outcomes — with full support from Product, Engineering, and Data.
Drive Student Engagement at Scale
Own the full engagement funnel — from the moment a student signs up to their 50th action on the Winbox platform. You'll set the strategy, run the experiments, and move the metrics that matter.
Build an Experimentation Engine
Design and launch a prioritized roadmap of A/B tests across activation, engagement, and re-engagement. You'll be the person who figures out what actually works — and scales it.
Turn Data Into Student Outcomes
Diagnose why students engage (or don't) using behavioral data, then build strategies that close the gap. Your decisions will be grounded in evidence and measured in real student impact.
Lead a Mission-Aligned Team
You'll manage Heads of Agent Success, Specialist Services, and Student Safety — a team already doing incredible work that needs a leader to bring it all together.
Your First 90 Days
Analyze student behavior across the Winbox to identify the biggest engagement gaps.
Design a prioritized experiment roadmap across activation, engagement, and re-engagement.
Run your first experiments on 24-hour activation, 14-day engagement, and session completion.
The Candidate
You might be the one if…
You've built or owned engagement, lifecycle, or growth programs at a consumer app or tech company
You love data — not just reading dashboards, but designing experiments and acting on what you find
You've worked cross-functionally with Product, Engineering, and Data teams and know how to get things done
You're entrepreneurial — you don't wait for permission, you build the playbook
You care deeply about students and believe access to mentorship and tutoring can change lives
You're comfortable with ambiguity and energized by building something that doesn't fully exist yet
Must-have: A background in data analysis and management. Experience in education is a plus, but not required — we care more about your ability to use data and experimentation to drive engagement.
What we offer
We take care of our people so they can take care of students.
Ready to make an impact?
This role is invite-only. Express your interest below and if you're a strong fit, we'll reach out personally with an invitation to apply.