Fleetio

Head of GTM Enablement

Remote

Not SpecifiedCompensation
Expert & Leadership (9+ years)Experience Level
Full TimeJob Type
UnknownVisa
Transportation Technology, SoftwareIndustries

Requirements

The ideal candidate will have over 7 years of progressive experience in Sales Enablement, Revenue Enablement, or GTM Strategy roles within the SaaS industry. Proven success in leading high-impact enablement programs tied to business outcomes such as pipeline creation, conversion rates, and ACV growth is essential. Experience supporting outbound sales teams with prospecting playbooks, buyer-centric messaging, and account prioritization frameworks is required, along with strong business acumen and an understanding of how enablement connects to GTM motions, RevOps systems, and commercial strategy. Excellent cross-functional collaboration skills, including influencing without authority and partnering with Product Marketing, Sales Leadership, and Revenue Operations, are necessary. Familiarity with enablement tools and systems like Workramp and Gong is expected, and a passion for coaching, data-driven learning, and creating field-ready representatives is highly valued.

Responsibilities

The Head of GTM Enablement will lead the development and execution of an integrated enablement strategy to drive performance across Sales, Customer Success, and Channel teams, ensuring alignment with Revenue Operations and GTM priorities. This role involves designing programs that support outbound rigor, territory and account prioritization, and effective use of scoring models to enhance rep efficiency and targeting precision. Responsibilities include delivering a scalable onboarding and continuous learning framework focused on core competencies, ramp acceleration, and role-based productivity milestones. The Head of GTM Enablement will partner cross-functionally with RevOps, Product Marketing, Sales Leadership, and Channel teams to build enablement programs for new product launches, competitive positioning, and messaging adherence. They will develop and operationalize certification programs and deal-stage reinforcement aligned with sales methodologies, utilizing live deals for application. Utilizing data to identify skill and behavior gaps and collaborating with Sales Managers to deploy coaching programs that reinforce desired behaviors in live selling environments is key. The role includes owning and evolving an Enablement Scorecard to track adoption, performance lift, and enablement ROI across funnel stages, as well as scaling a high-performing enablement team with clear charters for onboarding, field readiness, content, and tooling. Leading high-impact enablement events such as Revenue Kickoff, Product Launch Playbooks, and Quarterly Readiness Sprints is also a core responsibility.

Skills

Go-to-Market Strategy
Sales Enablement
Customer Success Enablement
Channel Enablement
Onboarding
Continuous Learning
Revenue Operations
Product Marketing
Cross-functional Alignment
Data-driven Decision Making
Performance Management
Program Development
Strategic Planning

Fleetio

Fleet management software for tracking operations

About Fleetio

Fleetio provides fleet management software that helps organizations track, analyze, and improve their fleet operations. The software allows users to manage vehicles, equipment, parts, and operators in a streamlined manner. It operates on a subscription-based model, generating revenue through software licenses. Fleetio's platform is designed to be user-friendly and collaborative, making it easier for clients to manage their assets effectively. Unlike many competitors, Fleetio focuses on continuous enhancements to meet the changing needs of its users. The goal of Fleetio is to help businesses of all sizes improve their operational efficiency and manage their fleets more effectively.

Birmingham, AlabamaHeadquarters
2012Year Founded
$165.3MTotal Funding
SERIES_CCompany Stage
Automotive & Transportation, Enterprise SoftwareIndustries
201-500Employees

Risks

Emerging competition from Nayax's EasyFuelPlus could challenge Fleetio's market share.
Integration issues with Razor Tracking may affect customer satisfaction and retention.
Reliance on partnerships for new features poses risks if partners face difficulties.

Differentiation

Fleetio offers a comprehensive fleet management system with global reach and diverse clientele.
The platform integrates with FuelCloud and Fill-Rite for enhanced on-site fuel management.
Fleetio's mobile app now supports Spanish, broadening its accessibility to Spanish-speaking users.

Upsides

Fleetio's partnership with Razor Tracking enhances its vehicle and asset management capabilities.
The rise of electric vehicles presents opportunities for specialized EV fleet management tools.
Fleetio's focus on sustainability aligns with growing trends in eco-friendly fleet operations.

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