Director, GTM Technology & Operations

A little about us…Fleetio is a modern software platform that helps thousands of organizations worldwide 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 our Series D funding round 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: Fleetio overview video: https://www.youtube.com/watch?v=YoXyXTFWbkg Our careers page: https://www.fleetio.com/careers At Fleetio, we’re on a mission to make fleet operations easier and more efficient. As we grow, we’re investing in how our go-to-market teams operate, scale, and deliver value to customers. We’re looking for a Director of GTM Technology & Operations to lead the execution engine behind our GTM systems, programs, and processes. This role will own how our GTM technology and operations evolve to support the next phase of growth, ensuring our systems are scalable, our data is trusted, and our teams operate efficiently. You’ll partner closely with Sales, Marketing, Customer Experience, Finance, and Product to identify and eliminate friction across the full GTM funnel, from pipeline generation through deal close and expansion and drive measurable improvements in pipeline velocity, forecasting accuracy, and revenue efficiency. What you’ll be doing Drive alignment across teams and systems: Act as a strategic partner across GTM and technology teams to align priorities, resolve competing demands, and ensure execution stays focused on the highest-impact work. Connect systems, people, and goals so delivery is coordinated, transparent, and outcome-driven. Own GTM program portfolio and prioritization: Lead the GTM PMO function, ensuring the highest-impact initiatives are prioritized, resourced, and executed. Drive clear decision-making across competing priorities and ensure alignment between business goals and technology investments. Partner with leadership: Work closely with senior stakeholders to drive clarity and decision-making. Translate system and program progress into clear business impact and actionable insights. Act as a GTM operator, not just a systems leader: Develop a deep understanding of Fleetio’s funnel, from pipeline generation through deal close and expansion. Identify where friction exists across the GTM motion and partner with business leaders to improve conversion, velocity, and overall revenue efficiency. Own the business of GTM technology Build operational rigor: Establish PMO governance and operating rhythms: Build the frameworks that guide how work gets planned, prioritized, and tracked across GTM. Drive executive visibility through clear reporting, QBRs, and portfolio reviews. Support budget and resource planning: Partner on GTM technology budgeting and resource planning. Help prioritize investments, manage tradeoffs, and ensure resources are aligned to the highest-impact initiatives. Define and track what matters: Build and track metrics that connect system performance to business outcomes, including pipeline velocity, conversion rates, forecast accuracy, and rep productivity. Improve how we work Scale systems and processes: Evolve the systems and workflows that power our lead-to-cash operations to reduce friction, improve reliability, and support scale. Lead cross-functional delivery: Oversee execution across GTM systems, ensuring strong data integrity, consistent processes, and seamless collaboration across teams. Support change management: Drive adoption of new systems and processes, ensuring changes are well-communicated, well-supported, and lead to meaningful improvements in how teams operate. Build and lead a strong team Lead and develop a team of program managers and operations professionals. Create a culture focused on ownership, clarity, and delivering measurable business outcomes. What we’re looking for 12 to 15+ years of experience in technology operations, program management, or business operations Strong understanding of GTM systems and the lead-to-cash lifecycle (CRM, marketing automation, billing, and data systems) Experience defining system or program strategy and leading complex, cross-functional initiatives Proven ability to drive measurable business outcomes through systems and process improvements Demonstrated GTM fluency, with experience improving pipeline generation, conversion, forecasting, or revenue efficiency in a B2B SaaS environment Ability to balance strategy and execution in a fast-moving environment Strong communicator who can influence across technical and business stakeholders Experience managing metrics, planning processes, and operational frameworks Why this role matters You’ll play a critical role in helping Fleetio scale how we operate. Your work will directly impact how efficiently we generate revenue, how confidently we forecast, and how effectively our teams operate every day. Benefits Multiple health/dental coverage options (100% coverage for employee, 50% for family) Vision insurance Incentive stock options 401(k) match of 4% PTO - 4 weeks (increases at year two!) 12 company holidays + 2 floating holidays Parental leave - birthing parent (16 weeks paid) non-birthing (4 weeks paid) 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 Fully stocked kitchen with tons of drinks & snacks (BHM only) 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.