Director of Engineering

Stride, Inc. is an exciting startup focused on building and scaling an innovative educational platform for K-12 tutoring. The Director of Engineering will lead the platform engineering organization, overseeing Agile teams to deliver high-quality software solutions while fostering a strong engineering culture.

Responsibilities:

• Lead and scale a distributed organization of Software Engineers, QA professionals, and Scrum Masters, fostering a culture of accountability, learning, and high performance
• Own delivery execution across multiple Agile teams, ensuring predictable outcomes aligned to business priorities, customer commitments, and regulatory requirements
• Partner with Product, Business, Data Engineering, AI, Information Security, and Operations leaders to shape roadmaps, scope initiatives, and deliver differentiated platform capabilities
• Set and evolve engineering operating rhythms, including sprint planning, release management, dependency coordination, and continuous improvement practices
• Drive architectural standards and technical strategy across the platform, ensuring solutions are secure, compliant, performant, accessible, and scalable
• Make strategic trade-offs between short-term feature delivery and long-term technical investments, including identifying, prioritizing, and addressing technical debt to reduce risk and ensure sustainable scalability and efficiency
• Promote adoption of engineering best practices while maintaining agility and avoiding over-engineering
• Thrive in fast-paced, high-growth startup environments, balancing hands-on technical guidance with team leadership and execution
• Establish and track engineering metrics such as delivery throughput, quality, reliability, security posture, and team health; use data to improve outcomes
• Ensure strong DevOps and cloud practices, including CI/CD pipelines, observability, cost optimization, resiliency, and incident response
• Champion reliability engineering, disaster recovery planning, and business continuity processes aligned with uptime targets, RPO/RTO requirements, and customer SLAs
• Guide the development and deployment of AI-enabled features, collaborating with internal experts and vendors to integrate machine learning models, analytics, and intelligent automation into production systems
• Build strong cross-functional relationships with senior leaders and external partners; communicate complex technical concepts clearly to non-technical audiences
• Influence strategic technology decisions, including build vs. buy analyses, vendor partnerships, and long-term platform investments
• Develop organizational structures, career paths, hiring plans, and succession strategies to support growth
• Create an inclusive, feedback-rich environment that attracts and retains top talent while continuously raising the technical bar
• Represent Engineering in executive forums, providing visibility into progress, risks, capacity, and investment tradeoffs

Requirements:

• Bachelor's degree in computer science, engineering, or related field, or equivalent practical experience
• 10+ years of progressive experience in software engineering roles, including senior leadership of multi-team organizations
• Proven experience leading engineering teams at scale (20+ staff and contractors) delivering complex, customer-facing platforms
• Demonstrated success driving Agile delivery in high-growth or transformation environments
• Strong background in modern cloud-based architectures, DevOps practices, and distributed systems
• Experience building secure, compliant systems in regulated environments (e.g., education, healthcare, fintech, or government)
• Track record of shipping new product capabilities—including data-driven or AI-enabled features—into production
• Excellent people leadership skills, including coaching managers, building performance cultures, and developing technical leaders
• Experience establishing engineering metrics and operating models that improve velocity, quality, and predictability
• Strong strategic thinking paired with hands-on execution orientation
• Outstanding written and verbal communication skills with the ability to influence at the executive level
• Exceptional organizational skills and ability to manage competing priorities across a complex portfolio
• Ability to pass required background checks