VP, Engineering

HopSkipDrive

18h•$240,000 - $270,000•Remote

About The Position

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.

Requirements

Deep technical credibility rooted in the ability to engage constructively in architecture, system design, and engineering quality discussions as a collaborative peer to senior engineers and technical leaders.
Breadth across modern web, mobile, cloud, and marketplace-oriented environments, with the ability to reason across Ruby on Rails, React, native iOS and Android clients, and modern cloud infrastructure (AWS or GCP).
Experience evolving developer workflows to leverage automation and AI agents, with a fluent understanding of how these tools impact code quality, security, and velocity, and a proven track record of successfully driving developer adoption.
Proven leadership at scale, including experience managing engineering managers, designing organizational structures for teams of 30-60 engineers, and making deliberate talent decisions to optimize team health.
Thoughtful change leadership and the resilience to drive organizational or cultural shifts with empathy, clarity, and a proven ability to bring skeptical teams along.
Business and product centricity, with a history of balancing technical hygiene, reliability, architecture investments, operational realities, and near-term customer and business needs.
Excellent asynchronous communication skills, emphasizing clear written documentation and structured delegation that empowers remote engineering teams to operate with high autonomy.

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.