Head of GTM Enablement

GTM Enablement Leader

Position Overview

Fleetio is seeking a strategic and innovative GTM Enablement Leader with a proven track record of driving cross-functional alignment and measurable impact on seller performance. You will be accountable for building and scaling a modern enablement function that fuels productivity across Sales, Customer Success, Account Management, and Channel teams—from onboarding to outbound to expansion. At Fleetio, enablement is viewed as more than just content and training; it's about fostering a culture of excellence, embedding rigor into our go-to-market motions, and leveraging data to drive behavior change.

Fleetio is a leading modern software platform for fleet operations, operating in a dynamic transportation technology market. We are experiencing significant growth, evidenced by our Series D funding round of $450M in March 2025, and are on an exciting trajectory.

Responsibilities

• Lead Enablement Strategy: Develop and execute an integrated enablement strategy aligned with Revenue Operations and GTM priorities to drive performance across Sales, Customer Success, and Channel teams.
• Design Performance Programs: Create programs that enhance outbound rigor, territory and account prioritization, and effective use of scoring models to enable reps to work smarter and target with precision.
• Develop Learning Frameworks: Deliver a scalable onboarding and continuous learning framework focused on core competencies, ramp acceleration, and role-based productivity milestones.
• Cross-Functional Partnerships: Collaborate with RevOps, Product Marketing, Sales Leadership, and Channel teams to build enablement programs supporting new product launches, competitive positioning, and messaging adherence.
• Operationalize Certification & Reinforcement: Develop and operationalize certification programs and deal-stage reinforcement aligned with sales methodologies (e.g., MEDDPICC, SPICED), utilizing live deals for practical application.
• Data-Driven Coaching: Utilize data to identify skill and behavior gaps, working closely with Sales Managers to deploy coaching programs that reinforce desired behaviors in live selling environments.
• Enablement Scorecard Ownership: Own and evolve an Enablement Scorecard to track adoption, performance lift, and enablement ROI across funnel stages.
• Scale Enablement Team: Scale a high-performing enablement team with clear charters for onboarding, field readiness, content, and tooling.
• Lead Enablement Events: Lead high-impact enablement events, such as Revenue Kickoff, Product Launch Playbooks, and Quarterly Readiness Sprints.

What's in it for You

• Strategic Impact: Be part of a high-performance culture where Enablement is a strategic lever, not merely a support function.
• Empowerment: You will be empowered to implement a data-informed, behavior-focused approach to seller development.
• Collaboration: Collaborate with peers in GTM Systems and Revenue Operations to build a unified revenue engine.
• Remote-First: Work in a remote-first environment with a leadership team that values execution and autonomy.

Requirements

• Experience: 7+ years of progressive experience in Sales Enablement, Revenue Enablement, or GTM Strategy roles within the SaaS industry.
• Program Success: Proven success in leading high-impact enablement programs tied to business outcomes such as pipeline creation, conversion rates, and ACV growth.
• Outbound Support: Experience supporting outbound sales teams with prospecting playbooks, buyer-centric messaging, and account prioritization frameworks.
• Business Acumen: Strong business acumen with an understanding of how enablement connects to GTM motions, RevOps systems, and commercial strategy.
• Collaboration Skills: Excellent cross-functional collaboration skills, with experience in influencing without authority and partnering effectively with Product Marketing, Sales Leadership, and Revenue Operations.
• Enablement Tools: Experience with enablement tools and systems (e.g., Workramp, Gong, etc.).
• Passion: A passion for coaching, data-driven learning, and developing field-ready representatives.

Company Information

• About Fleetio: Fleetio is a modern software platform that helps thousands of organizations worldwide manage their fleet operations.
• Culture Videos: https://fleet.io/culture
• Fleetio Overview: https://www.youtube.com/watch?v=IlvIbwZT3oU
• Platform Features: https://www.fleetio.com/features
• Careers Page: https://www.fleetio.com/careers

Application Instructions

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