GTM Enablement

Summary

Join Fleetio as a strategic and innovative GTM Enablement Leader to build and scale a modern enablement function. You will be responsible for driving cross-functional alignment and improving seller performance across Sales, Customer Success, Account Management, and Channel teams. The role involves designing and executing an integrated enablement strategy, developing onboarding and continuous learning frameworks, and partnering with cross-functional teams. You will also use data to identify skill gaps and deploy coaching programs. This position requires a proven track record of success in sales enablement and a passion for coaching and data-driven learning. Fleetio offers a remote-first environment and a high-performance culture.

Requirements

• 7+ years of progressive experience in Sales Enablement, Revenue Enablement, or GTM Strategy roles in SaaS
• Proven success leading high-impact enablement programs tied to business outcomes (pipeline creation, conversion rates, ACV growth)
• Experience supporting outbound sales teams with prospecting playbooks, buyer-centric messaging, and account prioritization frameworks
• Strong business acumen with an understanding of how enablement connects to GTM motions, RevOps systems, and commercial strategy
• Excellent cross-functional collaboration skills with experience influencing without authority and partnering with Product Marketing, Sales Leadership, and Revenue Operations
• Experience with enablement tools and systems (e.g. Workramp, Gong, etc.)
• Passionate about coaching, data-driven learning, and creating field-ready reps, not just trained ones

Responsibilities

• Lead the development and execution of an integrated enablement strategy that drives performance across Sales, Customer Success, and Channel teams — tightly aligned with Revenue Operations and GTM priorities
• Design programs that support outbound rigor, territory & account prioritization, and effective use of our scoring models, enabling reps to work smarter and target with precision
• Deliver a scalable onboarding and continuous learning framework focused on core competencies, ramp acceleration, and role-based productivity milestones
• Partner cross-functionally (RevOps, Product Marketing, Sales Leadership, Channel) to build enablement programs that support new product launches, competitive positioning, and messaging adherence
• Develop and operationalize certification programs and deal-stage reinforcement aligned to our sales methodology (e.g. MEDDPICC or SPICED), using live deals to drive application
• Use data to identify skill and behavior gaps, and work closely with Sales Managers to deploy coaching programs that reinforce desired behaviors in live selling environments
• Own and evolve an Enablement Scorecard that tracks adoption, performance lift, and enablement ROI across funnel stages
• Scale a high-performing enablement team, with clear charters across onboarding, field readiness, content, and tooling
• Lead high-impact enablement events (e.g. Revenue Kickoff, Product Launch Playbooks, Quarterly Readiness Sprints)

Benefits

• 100% health/dental coverage (50% coverage for family)
• Vision insurance
• Incentive stock options
• 401(k) match of 4%
• PTO - 4 weeks
• 8 company holidays + 2 floating holidays
• Parental and bonding leave
• Dependent care and medical FSA
• Short and long-term disability
• Community service funds
• Professional development funds
• Health and wellness initiatives
• Mac laptop + new hire equipment stipend
• Monthly catered lunches
• Fully stocked kitchen with tons of drinks & snacks
• Remote working friendly since 2012 #LI-REMOTE