Director of Engineering (Product)

Remote (United States)

Job Details

Location: United States

Workplace: Remote

Employment Type: Full-time

Core Areas: Engineering Leadership, Product Engineering, Software Architecture, Engineering Team Management, Technical Strategy, Production Reliability, Software Quality & Security, Engineering Process Improvement

Compensation: $210,000-$240,000 annually, plus equity

About the Role

The Director of Engineering (Product) will lead multiple product engineering squads, taking ownership of technical execution, engineering delivery, team performance, and organizational development. This leadership position is responsible for ensuring engineering teams achieve product and business objectives while maintaining high standards for software quality, scalability, security, and operational efficiency. Key priorities include guiding architecture decisions, aligning engineering investments with product strategy, and building effective teams capable of delivering sustainable results.

The role combines strategic technical leadership with hands-on engineering judgment, people management, and cross-functional execution. Responsibilities include overseeing teams developing technology-driven educational scheduling products, partnering with Product and other stakeholders, and guiding engineering decisions across software systems and technology platforms. The technology environment includes React, Python, AWS, and MongoDB, with an emphasis on scalable architecture, reliable production systems, and continuous engineering improvement.

What You'll Do

• Lead multiple product engineering squads, maintaining direct accountability for engineering delivery, team performance, and achievement of squad goals.
• Partner with Product and cross-functional stakeholders to establish squad objectives and align engineering priorities with product and business goals.
• Develop engineering staffing strategies that balance organizational priorities, squad requirements, available resources, and business constraints.
• Guide critical technical and architectural decisions to improve engineering efficiency, software quality, and the ability of teams to deliver against product objectives.
• Oversee engineering development priorities and ensure technical decisions support broader product strategy and business outcomes.
• Increase the effectiveness and impact of engineering squads through improvements in engineering culture, development processes, tooling, and technology.
• Manage critical relationships with internal and external stakeholders whose work enables or depends on engineering delivery.
• Empower engineering teams to execute independently while maintaining final responsibility for technical and operational results.

• Establish and improve engineering practices that integrate software quality throughout the development lifecycle, both within individual squads and across the engineering organization.
• Promote continuous learning from production incidents, software failures, and operational errors to strengthen engineering practices and system reliability.
• Advance security, software testing, and application scaling practices to maintain high standards for production systems.
• Serve as the escalation point for major production issues requiring senior engineering leadership and technical judgment.
• Implement processes and technology improvements that reduce production risks, prevent recurring incidents, and minimize the need for senior-level escalations.

• Directly recruit, hire, and manage engineering team members across multiple product squads.
• Guide strategic and tactical engineering execution primarily through team leadership, delegation, and employee empowerment.
• Take responsibility for employee retention, professional development, and team growth while aligning individual contributions with business needs and role expectations.
• Manage individual performance through regular feedback, coaching, and clear guidance on responsibilities and expected outcomes.
• Support engineers in meeting and exceeding performance expectations while maintaining accountability for team results.
• Build healthy, effective engineering teams capable of delivering business value sustainably, efficiently, and at a consistently high level of quality.

• Maintain high engineering delivery velocity while ensuring squads understand their objectives, priorities, and expected outcomes.
• Identify and remove obstacles involving multiple engineering squads, departments, or cross-functional stakeholders that interfere with product delivery.
• Ensure engineering team members collaborate effectively with other squads and business functions.
• Review sprint retrospectives, project progress, and team feedback to identify opportunities for operational and process improvements.
• Translate lessons from team performance and delivery challenges into practical improvements in engineering execution.

• Take hands-on ownership of challenging or business-critical engineering needs when direct involvement is necessary, while prioritizing team empowerment whenever possible.
• Proactively identify opportunities to improve the effectiveness, technical capabilities, and operating practices of the broader engineering organization.
• Accelerate team members' technical judgment and decision-making through pairing, technical reviews, coaching, and direct support.
• Represent engineering teams and the organization in internal and external discussions, including important technical and business conversations.

Qualifications

Required Experience

• Previous experience in technical leadership positions with responsibility for engineering execution and measurable business, product, and technical outcomes, such as technical lead, engineering manager, or engineering director.
• Demonstrated success managing and scaling multiple engineering teams while balancing direct individual contributions with leadership responsibilities.
• Hands-on software development and system design experience involving complex architectures with demanding scalability, security, and product requirements.
• Experience guiding engineering organizations through major technical decisions, changes in system scale, and the maturation of technology platforms supporting mission-critical products.
• Experience representing engineering organizations and companies in high-stakes internal and external discussions.

Required Skills

• Ability to lead multiple engineering squads, establish technical priorities, manage engineering performance, and drive product development toward defined business outcomes.
• Strong technical judgment in software architecture, system design, engineering trade-offs, and the development of scalable, secure software platforms.
• Ability to evaluate technical challenges and guide engineering decisions involving software quality, security, testing, scaling, and production reliability.
• Capability to adapt quickly to unfamiliar technology stacks and become effective across different software development environments. The current technology stack includes React, Python, AWS, and MongoDB; direct experience with every technology is not required.
• Ability to establish engineering staffing strategies, support employee development, manage performance, and improve retention across multiple teams.
• Experience improving engineering processes, development workflows, technical tooling, and organizational practices to increase team effectiveness.
• Ability to coordinate engineering work with Product and cross-functional stakeholders while resolving dependencies and delivery obstacles.
• Strong problem-solving skills and a proactive, solutions-oriented approach to ambiguous, fast-moving environments, particularly startup settings.
• Ability to take ownership of critical technical and organizational challenges while empowering engineering teams to make effective decisions.
• Commitment to delivering exceptional results for customers through reliable engineering execution and continuous improvement.

Preferred Qualifications

• Previous experience with or demonstrated interest in educational technology products.

Benefits

• Comprehensive health insurance.
• Parental leave.
• 401(k) retirement benefits.
• Unlimited paid time off (PTO).
• Access to coworking spaces.
• Equity participation in a growing startup.