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!

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.

• 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.

• 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.

• 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.

• Lead and develop a team of program managers and operations professionals. Create a culture focused on ownership, clarity, and delivering measurable business outcomes.

• 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…