Student Success Agency
Director of Student Services
🇺🇸
Remote - US
🕑
Full-Time
💰
TBD
💻
Academic Advising
🗓️
April 28th, 2026
Edtech
9-12
Edtech.com's Summary
Student Success Agency is hiring a Director of Student Services. The role involves diagnosing and improving student engagement with the Winbox platform through designing and running experiments, building engagement strategies, and leading cross-functional teams to increase sign-ups, activation, and sustained usage throughout the academic year.
Highlights
- Lead efforts to understand and improve student engagement with the Winbox platform at multiple stages: sign-up, activation, early use, sustained engagement, and re-engagement.
- Design and oversee execution of strategies and experiments aimed at increasing student actions and session completion rates.
- Collaborate cross-functionally with product, customer success, data analytics, and operations teams.
- Manage engagement strategies that cover initial 24-72 hours, first 60 days, and reactivation campaigns at 30, 60, and 90 days of inactivity.
- Utilize behavioral data and analytics to drive insights and operational improvements.
- Require 7+ years of experience in product engagement, growth, or student success strategy, with strong analytical skills and experience running experiments.
- Ideal candidates have backgrounds in EdTech growth, product lifecycle marketing, consumer engagement platforms, behavioral science, or marketplace/platform engagement.
- Accountable for increasing metrics such as sign-ups, actions taken by students, and session rates across partner school districts.
- Will develop an experimentation roadmap and launch engagement initiatives within the first 90 days.
- Passion for improving student outcomes by ensuring active and meaningful use of mentoring, tutoring, and guidance services.
Director of Student Services Full Description
Director of Student Services
Student Success Agency (SSA) - Remote-First, US-Based - Full-Time
About Student Success Agency
Student Success Agency (SSA) is the first agency dedicated to representing middle and high school students as they prepare for life after graduation. We believe that if LeBron James has an Agent and Taylor Swift has an Agent, every teenager deserves someone advocating for their future as well.
SSA partners with school districts to give secondary school students on-demand access to personalized support through one platform, The Winbox. Through the app, students can connect with a dedicated 1:1 mentor (their Agent), academic tutors, college and career readiness guidance, and licensed social workers.
SSA was founded in 2012 and has been featured in TEDx, Forbes 30 Under 30: Education, Inc. 5,000, and the White House's Datapalooza.
The Role
We are hiring a Director of Student Services to own one of the most important problems in our company:
"How do we get more students to sign up, activate, and consistently use the Winbox platform?"
You will design and run experiments, build systems, and lead cross-functional teams to dramatically improve how students engage with SSA.
Key Responsibilities
Diagnose Why Students Engage
- Diagnose why students engage or do not engage with The Winbox 24-hours after initial sign-upIf students DO engage, diagnose why they stay engaged for a full academic yearIf students DO engage, diagnose why students do NOT stay engaged for a full academic year
Create a Strategy for Closing the Engagement Gap
- Create a strategy to test SSA's initial first 60-day engagement tactics after sign-up, focusing on the first 48-72 hoursCreate a strategy to test SSA's engagement tactics after the first 60 daysCreate a strategy to test SSA's re-engagement tactics after students stop engaging
Oversee Execution of Engagement Strategies
- Oversee execution of SSA's engagement strategy after immediate student sign-upOversee execution if students take action (become active) 24-hours after initial sign-upOversee re-engagement strategy if students go inactive for 90+ days
Success Metrics
The Director of Student Services will be responsible for designing and executing strategies that increase:
Sign Ups
% of eligible students who sign up and onboard to the Winbox
Students with 1+ Action
% of students with 1+ actions on the Winbox 24-hours or more after initial sign up
Students with 5+ Actions
% of students with 5+ actions on the Winbox 24-hours or more after initial sign up
Students with 50+ Actions
% of students with 50+ actions on the Winbox 24-hours or more after initial sign up
Session Rate
% of unique students at each account who complete a session in The Winbox
Student Engagement Journey
1 Sign-Up (0-24 hours)
Student completes registration and account creation.
2 Activation (24 Hours - 14 Days)
Student takes their first meaningful action (message, session booking, etc.).
3 Early Engagement (14 days - 60 Days)
Student develops repeat usage habits with the platform.
4 Sustained Engagement (60+ Days)
Student continues engaging throughout the academic year.
5 Re-Engagement
Student returns to the platform after becoming inactive.
What You'll Own
Student Activation
• Improve sign-up rates for The Winbox
- Drive first meaningful actions
- Improve engagement within the first 24-72 hours
Engagement and Habit Formation
- Improve the first 14-60 day engagement experience
- Increase repeat student actions on the platform
- Help students develop habits of engagement with mentors
Re-Engagement
- Design 30-day reactivation campaigns
- Design 60-day reactivation campaigns
- Design 90-day reactivation campaigns
Cross-Functional Leadership
- Partner with Product
- Partner with Customer Success
- Partner with Data and Analytics
Qualifications
⚠️ This role requires 7+ years of experience. Please do not apply if you are early in your career — we will not be able to respond to applications that do not meet this threshold.
- 7+ years of experience in product engagement, growth, or student success strategy
- Strong analytical mindset and experience working with behavioral data
- Experience designing and running engagement experiments
- Ability to translate insights into operational systems and playbooks
- Experience working cross-functionally with product, operations, and customer teams
- Passion for improving outcomes for students
Ideal Background
We are looking for someone who thrives at the intersection of data, product strategy, and behavioral engagement. Ideal candidates may come from:
- EdTech growth or engagement leadership
- Product growth / lifecycle marketing
- Consumer engagement platforms
- Behavioral science / student success strategy
- Marketplace or platform engagement teams
Your First 90 Days
1 Diagnose Engagement
Analyze student behavior across the Winbox platform to identify the biggest engagement gaps.
Analyze student behavior across the Winbox platform to identify the biggest engagement gaps.
2 Build an Experimentation Roadmap
Design a prioritized roadmap of engagement experiments across student activation, early engagement, and re-engagement.
3 Launch Engagement Experiments
Run your first set of experiments focused on improving 24-hour activation, first 14-day engagement, and session completion.
Why This Role Matters
Student Success Agency serves thousands of students across the country through partnerships with school districts. But our mission is bigger than sign-ups.
Our mission is engagement that changes student outcomes.
The Director of Student Services will play a critical role in ensuring students do not just sign up for The Winbox. They will actively use it to access mentors, tutoring, and guidance that changes the trajectory of their lives.
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