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, and our software solves the biggest transportation challenges facing schools and school districts across the country.
Founded by three moms, we've facilitated over five million rides across 20+ states. We are a Series D company, have raised $100M to date, and are consistently recognized as a fast-growing technology leader.
How We Work
We're an AI-forward company. We use AI tools to draft, analyze, build, and ship faster, and we invest in training and governance. We don't expect you to be an expert, but we do expect curiosity and a readiness to use the best tools available.
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. We embrace the power of AI to deliver value faster while keeping humans at the center. Our teams operate through shared ownership and close collaboration. 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 technical credibility rooted in the ability to engage constructively in architecture, system design, and engineering quality discussions.
- Breadth across modern web, mobile, cloud, and marketplace-oriented environments (Ruby on Rails, React, native iOS/Android, AWS/GCP).
- Experience evolving developer workflows to leverage automation and AI agents.
- Proven leadership at scale, including experience managing engineering managers and designing organizational structures for teams of 30-60 engineers.
- Thoughtful change leadership and the resilience to drive organizational or cultural shifts.
- Business and product centricity, with a history of balancing technical hygiene, reliability, and business needs.
- Excellent asynchronous communication skills.
Our Investment In You
We want you to be an owner in our company, so every full-time employee has equity. We offer flexible vacation, medical, dental, vision and life insurance, 401(k), FSA, and an opportunity to work for a uniquely positioned, VC-backed company.
- Salary Range: $240,000 - $270,000 + bonus (based on location).
- Location: Fully remote in AZ, CA, CO, DC, FL, GA, IL, IN, KS, MA, MD, MI, MN, MO, NC, NJ, NM, NV, NY, OK, OR, SC, TN, TX, UT, VA, WA, WI.
HopSkipDrive is an equal opportunity employer.