Fleetio

Director, GTM Technology – Operations

Fleetio

full-time

Posted on:

Location Type: Remote

Location: United States

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Job Level

Lead

About the role

  • 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.

Requirements

  • 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
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)
Applicant Tracking System Keywords

Tip: use these terms in your resume and cover letter to boost ATS matches.

Hard Skills & Tools
program managementtechnology operationsGTM systemslead-to-cash lifecycleCRMmarketing automationbilling systemsdata systemsmetrics managementoperational frameworks
Soft Skills
strategic partnershipdecision-makingcommunicationinfluencecross-functional collaborationchange managementteam leadershipownershipclaritymeasurable outcomes