VP of Engineering

About the Company

At HopSkipDrive, our mission is to create opportunity for all through mobility. We're the leader in safe, fast, and simple supplemental student transportation, connecting kids to highly-vetted caregivers through our marketplace and software.

Responsibilities

• Lead and scale a high-performing engineering organization by establishing career growth paths and structural changes
• Engage in system design and architecture discussions across Ruby on Rails, React, and iOS/Android platforms
• Pioneer the integration of AI and agentic capabilities into the software development lifecycle
• Own engineering department delivery, operational excellence, and reliability
• Partner with CPTO and SVP of Product to align technical strategy with product vision
• Manage department fiscal health, including headcount and infrastructure budgets

Requirements

• Proven leadership managing engineering managers and teams of 30-60 engineers
• Deep technical credibility in architecture and system design
• Experience with Ruby on Rails, React, native iOS, Android, and cloud infrastructure (AWS or GCP)
• Experience evolving developer workflows using automation and AI agents
• Strong asynchronous communication and documentation skills for remote environments
• Ability to balance technical hygiene with business and product needs

Benefits

• Equity stock options
• Flexible vacation
• Medical, dental, vision, and life insurance
• 401(k) and FSA