VP, Engineering
About the role
Who We Are
HopSkipDrive's Product & Technology organization is the heart of our competitive advantage, building the technologies that have and continue to transform student transportation. Our applications span web and mobile, B2B and B2C, operational and transformational. We embrace the power of AI to allow us to deliver more value to our customers faster, while keeping humans at the center of our work. Our teams operate through shared ownership and close collaboration rather than functional handoffs. We value leaders who can navigate complex tradeoffs across customer experience, operational realities, technical scalability, and long-term platform health.
As the VP of Engineering, you will lead our engineering organization through its next phase of scale and development. Partnering closely with the Chief Product & Technology Officer (CPTO) and the SVP of Product, you will drive execution, foster a high-performance culture, and lead our transition toward an AI-accelerated engineering environment.
Key Responsibilities
- Lead and scale a high-performing engineering organization by building deep trust, diagnosing organizational strengths, and establishing the career growth paths and structural changes required to elevate performance.
- Engage deeply and credibly in system design and architecture discussions, helping senior engineers navigate complex technical trade-offs across our platform (Ruby on Rails, React, iOS/Android), service boundaries, and modern infrastructure investments.
- Pioneer the integration of AI and agentic capabilities into our software development lifecycle, spanning the evaluation of new technical infrastructure, coaching teams through change management, and establishing the workflows, testing methodologies, and QA guardrails required to safely accelerate shipping velocity.
- Own the Engineering department's delivery and operational excellence, ensuring predictable, high-quality execution, world-class reliability, and continuous improvement of technical health and process discipline.
- Partner closely with the CPTO, SVP of Product, Design, Data, and Operations to align product vision with technical strategy and drive unified customer and business outcomes.
- Manage the engineering department's fiscal health, including headcount, contractors, software, and infrastructure budgets.