VP, Engineering

HopSkipDrive

Lead HopSkipDrive's engineering organization, driving AI integration and team performance for growth. Collaborate with product leaders to enhance technology in student transportation.

Posted 5/30/2026full-timeRemote • Arizona, California, Colorado, District of Columbia, Florida, Illinois, Kansas, Maryland, Massachusetts, Minnesota, Missouri, Montana, Nevada, New Jersey, New Mexico, New York, North Carolina, Oklahoma, Oregon, South Carolina, Tennessee, Texas, Utah, Virginia, Washington, Wisconsin • 🇺🇸 United StatesLead💰 $240,000 - $270,000 per yearWebsite

Tech Stack

Tools & technologies

AndroidAWSCloudGoogle Cloud PlatformiOSReactRubyRuby on Rails

About the role

Key responsibilities & impact

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.

Requirements

What you’ll need

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.

Benefits

Comp & perks

flexible vacation
medical insurance
dental insurance
vision insurance
life insurance
401(k)
FSA
equity

ATS Keywords

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Applicant Tracking System Keywords

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Hard Skills & Tools

Ruby on RailsReactiOSAndroidAWSGCPautomationAI integrationsystem designarchitecture

Soft Skills

leadershipcollaborationchange managementcommunicationempathyorganizational designresiliencedocumentationdelegationteam health