VP of Engineering

Salary: Not Specified Location Type: Remote (United States Only) Employment Type: Not Specified

Position Overview

Fleetio is seeking an innovative and experienced VP of Engineering to lead and scale our growing engineering organization. As a key member of Fleetio’s executive leadership team, you will be instrumental in shaping our technical strategy, fostering a culture of excellence, and ensuring the delivery of customer-focused solutions that empower thousands of organizations to manage their fleet operations worldwide. You will provide strategic direction to our Engineering teams across Product, Platform, Mobile, and Quality Engineering, championing an inclusive and high-performing culture, and driving the evolution of our SaaS platform. If you are passionate about technology, people, and solving tough real-world problems, we’d love to connect with you!

About Fleetio

Fleetio is a modern software platform that helps thousands of organizations around the world manage their fleet operations. Transportation technology is a hot market and we’re leading the charge, with raving fans and new customers signing up every day. We raised $450M in Series D in March of 2025 and are on an exciting trajectory as a company. Fleetio is also a proud founding member of the Rails Foundation!

More About Our Team and Company

• Culture Videos: https://fleet.io/culture
• Engineering Culture, Interview Process, and Videos: https://www.fleetio.com/careers/engineering
• Fleetio Overview Video: https://www.youtube.com/watch?v=IlvIbwZT3oU
• Fleetio Go Overview Video: https://www.fleetio.com/go
• Fleetio Platform Features: https://www.fleetio.com/features
• API Docs: developer.fleetio.com
• Test Drive Fleetio: https://www.fleetio.com/register

Who You Are

The ideal candidate for this role possesses a blend of leadership skills, technical expertise, business acumen, and strategic vision. You have a proven background in building products and driving innovation in a SaaS environment. Your leadership experience includes successfully managing and inspiring high-performing engineering teams, driving innovation, and fostering a highly collaborative work culture. You exhibit strategic problem-solving skills, adaptability to a fast-paced environment, and a commitment to delivering high-quality, user-centric solutions. This role is part of the Executive Leadership team and will report directly to the CTO.

Your Impact

• Develop and execute the engineering vision and strategy in alignment with Fleetio's company objectives and product roadmap.
• Lead, inspire, and grow a distributed engineering organization spanning Product, Mobile, Quality, and Platform teams.
• Foster a culture of high performance, innovation, continuous improvement, and psychological safety within engineering.
• Partner closely with Product, Design, and other business leaders to define product roadmaps, prioritize initiatives, and deliver scalable, high-quality solutions.
• Champion technical excellence, code quality, and engineering best practices to ensure reliable, secure, and performant systems.
• Own headcount planning, organizational design, and talent development to support rapid growth and business needs.
• Represent Fleetio as a technology thought leader internally and externally, including at industry events and conferences.
• Oversee budgets, vendor relationships, and compliance initiatives for engineering domains.

Your Experience

• Proven experience in leading and scaling high-performing engineering organizations (ideally 5+ years in executive or senior engineering leadership roles at high-growth SaaS companies and leading engineering teams larger than 50 people).
• Track record of overseeing multiple engineering teams and director+ leaders across different engineering disciplines.
• Deep knowledge of modern SaaS products.
• Ability to define and articulate a technical and organizational vision.