Director of Engineering

Job Description

Summary: K12 Tutoring is an exciting startup within Stride, Inc.'s portfolio of companies, focused on building and scaling an innovative educational platform and service offering. Our aim is to enable students in grades K-12 to achieve their educational goals through receiving high-quality, personalized online tutoring from expert, certified teachers. We currently serve families directly, in addition to partnering with school districts and similar organizations to serve their student populations. Over time we plan to expand the product and business further to support a broader set of educational needs for a wider range of customers. 

The Director of Engineering leads K12 Tutoring's platform engineering organization, overseeing multiple cross-functional Agile teams responsible for building secure, scalable, accessible, and high-performing software solutions across our customer segments—including schools, districts, and families. This leader partners closely with Product, Data, AI, Information Security, DevOps, Enterprise Architecture, and Business stakeholders to translate strategy into execution, delivering high-quality customer experiences while building a strong engineering culture rooted in technical excellence, continuous improvement, and operational rigor.

The Director is accountable for technical architecture, delivery velocity, system reliability, team development, and long-term platform evolution, including the integration of AI-powered learning tools into the K12 Tutoring ecosystem. This role reports to the General Manager, K12 Tutoring.

Essential Functions, Duties and Responsibilities: Reasonable accommodations may be made to enable individuals with disabilities to perform the essential duties.

• 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.

Supervisory Responsibilities: Directly supervises 6-8 full-time equivalent (FTE) regular employees, plus up to 30 contractors as needed.  Carries out supervisory responsibilities in accordance with the organization's policies and applicable laws. Responsibilities include interviewing, hiring, and training employees; planning, assigning, and directing work; appraising performance; rewarding and disciplining employees; addressing complaints and resolving problems.

Minimum Required Qualifications:   

• 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.
   

Certificates and Licenses: None required.
 

COMPENSATION & BENEFITS: Stride, Inc. considers a person's education, experience, and qualifications, as well as the position's work location, expected quality and quantity of work, required travel (if any), external market and internal value when determining a new employee's salary level.  Salaries will differ based on these factors, the position's level and expected contribution, and the employee's benefits elections.  Offers will typically be in the bottom half of the range. 
 

We anticipate the salary range to be $132,000-$199,000.  Eligible employees may receive a bonus. This salary is not guaranteed, as an individual's compensation can vary based on several factors.  These factors include, but are not limited to, geographic location, experience, training, education, and local market conditions. Stride offers a robust benefits package for eligible employees that can include health benefits, retirement contributions, and paid time off. 

Work Environment: The work environment characteristics described here are representative of those an employee encounters while performing the essential functions of this job. Reasonable accommodations may be made to enable individuals with disabilities to perform the essential functions.

• This position is remote and open to residents of the 50 states, D.C.

The above job is not intended to be an all-inclusive list of duties and standards of the position. Incumbents will follow any other instructions, and perform any other related duties, as assigned by their supervisor.  All employment is "at-will" as governed by the law of the state where the employee works.  It is further understood that the "at-will" nature of employment is one aspect of employment that cannot be changed except in writing and signed by an authorized officer. 

Job Type

Regular

The above job is not intended to be an all-inclusive list of duties and standards of the position. Incumbents will follow any other instructions, and perform any other related duties, as assigned by their supervisor. All employment is "at-will" as governed by the law of the state where the employee works.  It is further understood that the "at-will" nature of employment is one aspect of employment that cannot be changed except in writing and signed by an authorized officer.

If you are a job seeker with a disability and require a reasonable accommodation to apply for one of our jobs, you can request the appropriate accommodation by contacting stridecareers@k12.com.

Equal Opportunity Employer/Protected Veterans/Individuals with Disabilities

Stride, Inc. is an equal opportunity employer. Applicants receive consideration for employment based on merit without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, disability or protected veteran status, or any other basis prohibited by federal, state, or local law. Stride, Inc. complies with all legally required affirmative action obligations. Applicants will not be discriminated against because they have inquired about, discussed, or disclosed their own pay or the pay of another employee or applicant.