VP, Engineering

🕒 May 30

🌵 Arizona, California, +24 more states – Remote

🌵 Arizona – Remote 🏄 California – Remote ⛰️ Colorado – Remote 🏛️ District of Columbia – Remote 🐊 Florida – Remote 🌽 Illinois – Remote 🌪️ Kansas – Remote 🎰 Nevada – Remote 🏖️ New Jersey – Remote 🌶️ New Mexico – Remote 🗽 New York – Remote 🌲 North Carolina – Remote 🌪️ Oklahoma – Remote 🌲 Oregon – Remote 🦀 Maryland – Remote 🍂 Massachusetts – Remote 🚗 Michigan – Remote ❄️ Minnesota – Remote 🏰 Missouri – Remote 🌴 South Carolina – Remote 🎸 Tennessee – Remote 🤠 Texas – Remote ⛷️ Utah – Remote ⚔️ Virginia – Remote ☕ Washington – Remote 🧀 Wisconsin – Remote

💵 $240k - $270k / year

⏰ Full Time

🔴 Lead

🖥 Software Engineer

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HopSkipDrive

WebsiteLinkedInAll Job Openings

51 - 200 employees

Founded 2014

🚗 Transport

📚 Education

🏢 Enterprise

💰 $37M Series D on 2022-09

Transport • Education • Enterprise

HopSkipDrive is a leading provider of innovative and scalable school transportation solutions, partnering with schools, districts, and counties to provide safe, reliable transportation for youth. They specialize in providing alternatives to traditional school bus routes, catering to students' non-routine needs, those in foster care, and students with special transportation requirements. HopSkipDrive also supports personalized and small group transportation solutions, and uses RouteWise AI technology for transportation optimization. Their service is known for being 40% more affordable than traditional underutilized bus routes. They also address challenges such as bus driver shortages and provide a flexible network of CareDrivers, ensuring safety and reliability.

📋 Description

• 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

• 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

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