[Hiring] Director, GTM Technology Operations & PMO @Fleetio

Role Description

We’re looking for a Director of GTM Technology Operations & PMO 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.
• Own GTM program portfolio and prioritization: Lead the GTM PMO function, ensuring the highest-impact initiatives are prioritized, resourced, and executed.
• Partner with leadership: Work closely with senior stakeholders to drive clarity and decision-making.
• Act as a GTM operator: Develop a deep understanding of Fleetio’s funnel, from pipeline generation through deal close and expansion.
• Own the business of GTM technology: Build operational rigor and establish PMO governance and operating rhythms.
• Support budget and resource planning: Partner on GTM technology budgeting and resource planning.
• Define and track what matters: Build and track metrics that connect system performance to business outcomes.
• Scale systems and processes: Evolve the systems and workflows that power our lead-to-cash operations.
• Lead cross-functional delivery: Oversee execution across GTM systems, ensuring strong data integrity and consistent processes.
• Support change management: Drive adoption of new systems and processes.
• Build and lead a strong team: Lead and develop a team of program managers and operations professionals.

Qualifications

• 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).
• Remote working friendly since 2012.