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Role overview

Fleetio is hiring a Head of GTM Enablement to design and lead scalable enablement programs across Sales, Marketing and Customer Success. In this senior leadership role you will partner with Revenue, Product and Operations to translate the company’s GTM strategy into practical enablement assets, processes, and tools. You will own onboarding programs, create training content, playbooks, and certification programs, and establish metrics to measure impact and continuously improve effectiveness. This remote-friendly role requires strategic thinking, instructional design expertise, and a track record of driving adoption of enablement initiatives in a fast-growing SaaS environment.

What you’ll do

Define and execute the GTM enablement strategy across Sales, Marketing, and Customer Success.
Build onboarding curriculums, product trainings, battle cards, content libraries, and certification programs.
Partner with Sales Leadership to design coaching programs, field enablement, and cadence planning.
Develop enablement content for product launches, marketing campaigns, and revenue initiatives; manage the enablement tech stack (CRM, LMS, knowledge base).
Measure impact using ramp time, win rate, quota attainment, time-to-productivity, and other metrics; continuously improve programs with data-driven experiments.
Collaborate with Product, Marketing and Revenue Operations to ensure timely and effective go-to-market content.
Scale enablement across regions as Fleetio grows globally.

What you’ll bring

8+ years of go-to-market enablement or sales enablement in SaaS.
Proven experience leading and scaling an enablement team in a fast-growing organization.
Strong instructional design, storytelling, and facilitation skills; experience with LMS and enablement tools.
Data-driven mindset with expertise in analytics and dashboards; ability to translate data into actionable insights.
Excellent cross-functional collaboration and communication skills; able to influence stakeholders without formal authority.
Remote-first mindset and willingness to work across multiple time zones.

Why Fleetio

Fleetio offers a remote-friendly culture, competitive compensation, comprehensive benefits, and significant opportunities to impact a growing SaaS company focused on modern fleet management.

Location

Remote

How to apply

Apply through the listing: https://job-boards.greenhouse.io/fleetio/jobs/4785305007

Fleetio