Director of Data

The Company

Outschool's mission is to inspire kids to love learning by reimagining the traditional educational system with flexible, engaging online learning experiences. Since launching in 2017, Outschool has grown significantly, serving over 1.5M learners and facilitating over $100M in annual bookings. The company fosters a culture of challenge, risk-taking, and growth, seeking individuals driven by curiosity and a desire to make an impact in pursuit of their mission.

The Role

We are hiring a Director of Data to lead Outschool’s Data team, responsible for developing data infrastructure, pipelines, and tools, and providing analytics and insights for data-informed decision-making. This is a critical leadership role requiring a blend of data strategy, people leadership, and hands-on technical contribution. The ideal candidate will shape Outschool’s data foundations, enhance self-serve analytics, and build applied AI/ML capabilities while collaborating across the business to maximize data impact.

Core Responsibilities:

• Lead, mentor, and grow a data team while remaining hands-on with data architecture, modeling, technical direction, and analytics.
• Contribute as an individual contributor in data engineering, data infrastructure, and analytics engineering, setting high standards for data quality, reliability, and usability.
• Lead data strategy and execution across core data systems (Redshift, dbt, Opensearch) and self-serve tools (Omni, Amplitude, Statsig).
• Partner cross-functionally with Product, Engineering, Marketing, Operations, Finance, and other teams to deliver trusted data resources and analytics.
• Collaborate with senior leadership on strategy, priorities, metrics, experimentation, and roadmap planning.
• Foster a culture of data quality, ownership, documentation, self-service, experimentation, and continuous improvement.
• Lead the adoption of self-serve data practices across the organization.
• Define and implement modern data practices to improve speed, trust, discoverability, and leverage in analytics, experimentation, and applied AI/ML.

Desired Experience & Skills:

• 10+ years of experience in data engineering, analytics engineering, analytics, data science, ML, software engineering, or related technical roles.
• 5+ years of management experience leading data, analytics, engineering, or ML teams.
• Strong experience with modern data infrastructure and analytics engineering (SQL, dbt, data modeling, pipeline reliability, warehouse architecture) and self-serve analytics systems (Omni, Looker, Amplitude, Statsig, Mode, Hex, or similar).
• Experience with deep analytics/data science, influencing stakeholders with data-informed decisions.
• Proven ability to balance leadership with hands-on technical contribution, especially in data engineering, infrastructure, or analytics engineering.
• Ability to lead multiple complex data initiatives from planning through execution and adoption.
• Deep experience leveraging experimentation, A/B testing, analytics, and metrics.
• Ability to align data strategy with business, product, and engineering priorities.
• Experience guiding ML Engineering work (search, recommendations, personalization, automation).
• Excellent communication and stakeholder management skills across technical, non-technical, and executive audiences.

Other Considerations:

• Experience in EdTech or building products for learners, educators, or families.
• Familiarity with search, discovery, recommendations, or marketplace systems.
• Experience with Redshift, dbt, Opensearch, Omni, Amplitude, or Statsig.
• Experience at a fast-paced startup or high-growth company.

Compensation:

• Canada: $220,000 - $275,000 CAD annually.
• US Tier 1 (San Francisco Bay Area, NYC): $260,000 - $357,500
• US Tier 2 (Rest of CA, Seattle, Boston, Chicago, Denver, Austin, Portland Metro): $221,000 - $303,875
• US Tier 3 (All other US locations): $195,000 - $268,125

Benefits & Culture:

• Shared Financial Success: Competitive salaries, stock options, retirement plans.
• Health: Comprehensive medical, dental, vision, disability, and life insurance.
• Wellness: Annual wellness stipend, access to coaching & therapy, pet wellness plans.
• PTO & Family Benefits: Generous PTO and family leave policies.
• Hybrid & Remote-Friendly: Distributed team across the U.S. and Canada, with a San Francisco office. Support for home office setup and internet for remote employees.
• Lifelong Learners: Annual budgets for professional development, DEI learning, and Outschool classes for children.
• Community Impact: Employee donation matching and support for Outschool.org's nonprofit programs.

Outschool is an equal opportunity employer committed to diversity. Reasonable accommodations are available upon request.