Director of Data

Outschool•Canada, KY

5d•$195,000 - $357,500•Hybrid

About The Position

Outschool is seeking a Director of Data to lead its Data team. This role is responsible for developing data infrastructure, pipelines, and tools, as well as providing analytics and insights to support data-informed decision-making. The Director of Data will shape the company's data foundations, enhance self-serve analytics tools, and build applied AI/ML capabilities. This critical leadership position requires a blend of data strategy, people leadership, and hands-on technical expertise. The ideal candidate will collaborate across business units to maximize the impact of data.

Requirements

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, with demonstrated proficiency in performance management, career development, and people logistics.
Strong experience with modern data infrastructure and analytics engineering, including SQL, dbt, data modeling, pipeline reliability, and warehouse architecture, as well building as self-serve analytics systems and practices using tools such as Omni, Looker, Amplitude, Statsig, Mode, Hex, or similar platforms.
Experience with deep analytics / data science, including influencing stakeholders with data-informed decisions and strategies.
Experience balancing data leadership responsibilities with hands-on technical contribution, especially in data engineering, data infrastructure, or analytics engineering.
Proven ability to lead multiple complex data initiatives from planning through execution and adoption.
Deep experience leveraging experimentation, A/B testing, analytics, and metrics to inform decisions.
Ability to align data strategy and execution with broader business, product, and engineering priorities.
Ability to guide ML Engineering work in areas such as search, recommendations, personalization, or applied automation, even if not personally the deepest ML practitioner.
Excellent communication and stakeholder management skills across technical, non-technical, and executive audiences.

Nice To Haves

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.

Responsibilities

Lead, mentor, and grow a small but mighty data team while remaining hands-on with data architecture, modeling, technical direction, and analytics.
Contribute directly as an individual contributor, particularly in data engineering, data infrastructure, and analytics engineering, helping establish high standards for data quality, reliability, and usability.
Lead data strategy and execution across Outschool’s core data systems, including Redshift, dbt, and Opensearch, and self-serve tools such as Omni, Amplitude, and Statsig.
Partner cross-functionally with Product, Engineering, Marketing, Operations, Finance, and other teams to deliver trusted, decision-ready data resources and analytics.
Collaborate with senior leadership to align on strategy, priorities, metrics, experimentation practices, and long-term roadmap planning.
Foster a culture of data quality, ownership, documentation, self-service, experimentation, and continuous improvement through mentorship and feedback.
Lead adoption of self-serve data practices across the organization, ensuring teams can access and use data effectively without requiring significant centralized support.
Help define and implement modern data practices that improve speed, trust, discoverability, and leverage across analytics, experimentation, and applied AI / ML.