VP, Engineering

About HopSkipDrive

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 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.

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 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.

Our Investment In You

• We want you to be an owner in our company and share in executing our vision, so every full-time employee has equity.
• In addition, 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 in a hugely attractive space with significant upside potential.
• HopSkipDrive is proud to operate as a drug-free workplace. HopSkipDrive is also committed to fair and equitable compensation practices. The salary range for this role is $240,000 - $270,000 + bonus. This position is remote and, as such, compensation will ultimately be in line with the location in which the position is filled. Final compensation for this role will be determined by several factors such as a candidate’s relevant work experience, skill set, certifications, and specific work location.
• The total compensation package for this role also includes equity stock options.

Equal Opportunity Employer

We are proud to be an equal opportunity employer. All qualified applicants will receive consideration for employment without regard to race, color, religion, gender, gender identity or expression, sexual orientation, national origin, genetics, disability, age, veteran status, or any other protected class.