VP, Engineering

At HopSkipDrive , our mission is to create opportunity for all through mobility. We're the leader in safe, fast, and simple supplemental student transportation through our marketplace, we connect kids to highly-vetted caregivers on wheels. Through our software, we solve the biggest transportation challenges facing schools and school districts across the country. Founded by three moms as a solution to their own transportation challenges, we've now facilitated more than five million rides across over over 20 states. We continue to grow rapidly — earning a spot on the Inc. 5000 list numerous times and the Deloitte 500 Fast-Growing Technology list. HopSkipDrive is a Series D company and has raised $100M to date. How we work We're an AI-forward company, and we expect every person on our team to be too. We use AI tools to do our best work — drafting, analyzing, building, and shipping faster than we could without them — and we invest in training, share what works, and govern AI use thoughtfully. We don't expect you to be an expert when you start. We do expect you to be curious, willing to learn, and ready to use the best tools available to move our mission forward. We're remote-first, mission-driven, and built for people who want to do work that matters with people who hold a high bar. 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. Who You Are You are a seasoned engineering leader who has stayed close to the technology and understands how to navigate organizational growth with empathy and clarity. You possess the strategic vision to lead an engineering department into its next phase of maturity while maintaining a deep, credible connection to the architecture and tech stack. What You Bring: Deep