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VP, Engineering

Remote - USA, CAN, MEX

Description

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!

A little about us… 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

This is a remote opportunity and is only open to candidates in the United States.

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, then build consensus to deliver against it.
  • Passion for coaching, mentoring, and growing engineering talent at all levels.
  • Strong business acumen and ability to partner cross-functionally at the executive level.
  • Experience empowering technical leaders and building an outstanding and inclusive engineering culture.
  • Excellent communication, collaboration, and stakeholder management skills.

Benefits

  • Multiple health/dental coverage options
  • Vision insurance
  • Incentive stock options
  • 401(k) match of 4%
  • PTO - 4 weeks
  • 12 company holidays + 2 floating holidays
  • Parental leave- birthing parent (16 weeks paid) non-birthing (4 weeks)
  • FSA & HSA options
  • Short and long term disability (short term 100% paid)
  • Community service funds
  • Professional development funds
  • Wellbeing fund - $150 quarterly
  • Business expense stipend- $125 quarterly
  • Mac laptop + new hire equipment stipend
  • Monthly catered lunches
  • Fully stocked kitchen with tons of drinks & snacks
  • Remote working friendly since 2012 #LI-REMOTE

Fleetio provides equal employment opportunities to all employees and applicants and prohibits discrimination and harassment. We celebrate diversity and are committed to creating an inclusive environment for all. All employment is decided on the basis of qualifications, merit and business need.

This application is not intended to and does not create a contract or offer of employment. Employment with Fleetio is at will.

If you have a disability or a special need that requires an accommodation to fill out the online application, please let us know by calling (205) 718-7500.

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