Lead and scale a high-performing engineering organization by building trust and establishing career growth paths.
Engage in system design and architecture discussions across Ruby on Rails, React, iOS/Android, and modern infrastructure.
Pioneer the integration of AI and agentic capabilities into the software development lifecycle.
Own engineering department delivery, operational excellence, reliability, and technical health.
Partner with CPTO and product leadership to align vision with technical strategy.
Manage engineering department budgets including headcount, contractors, software, and infrastructure.
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About HopSkipDrive
HopSkipDrive is pioneering safe, dependable transportation solutions for schools and families, creating opportunity through mobility. We connect students, including those with special needs or in foster care, to highly-vetted CareDrivers. Our platform supplements traditional transportation, partnering with over 400 school districts and 16,000 schools across 21 markets in 12 states. We have facilitated over 5 million rides, driving more than 95 million miles to ensure safe passage for every child.
How We Work
You will join a remote-first, mission-driven team dedicated to making a difference. We embrace an AI-forward approach, integrating AI tools into our daily workflows for drafting, analyzing, and building. Training, shared best practices, and thoughtful AI governance ensure you can use these powerful tools effectively. We foster connection through bi-weekly Town Halls, a hub program for local meetups, and virtual events. You will work with colleagues who value high standards and meaningful impact.
Engineering at HopSkipDrive
We craft robust, scalable solutions to complex transportation challenges. Our technology underpins a dynamic marketplace, processing millions of requests and optimizing routes for efficiency and safety. We leverage a modern data stack including SQL, dbt, and Snowflake for accurate data modeling and analysis. You will work with Salesforce CRM data models and integrate advanced AI capabilities to enhance operations and drive intelligent automation. We build tools that make a real difference in people's lives.
Why Join Us
Make a tangible social impact by solving critical transportation challenges for children.
Work in an AI-forward environment, with training and support to integrate cutting-edge tools into your daily work.
Contribute to a rapidly growing Series D company that has facilitated over 5 million safe rides.
Collaborate with a remote-first team that values high standards, operational rigor, and cross-functional partnership.
Own significant projects with autonomy, influencing outcomes with data and innovative solutions.
Benefits & Perks
Company equity for all full-time employees
Flexible vacation and time off policy
Medical, dental, vision, and life insurance
401(k) plan and Flexible Spending Account (FSA)
Mental health support and Employee Assistance Program (EAP)
11 paid holidays and a week-long company closure at year-end
Provided work-from-home office equipment and internet reimbursement