Head of GTM Enablement

We are looking for a strategic and innovative GTM Enablement Leader with a proven track record of driving cross-functional alignment and measurable impact on seller performance. You’ll 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, we believe Enablement is not just about content and training — it’s about building a culture of excellence, embedding rigor into our go-to-market motions, and using data to drive behavior change.

Fleetio is a modern software platform that helps thousands of organizations worldwide manage their fleet operations. Transportation technology is a hot market, and we’re leading the charge, with raving fans and new customers signing up daily. We raised $450M in our Series D funding round in March of 2025 and are on an exciting trajectory as a company.

More about our team and company:

• Watch our culture videos: https://fleet.io/culture
• Fleetio overview video: https://www.youtube.com/watch?v=IlvIbwZT3oU
• More about the Fleetio platform: https://www.fleetio.com/features
• Our careers page: https://www.fleetio.com/careers

What you’ll be doing

• 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)

What’s in it for you

• Be part of a high-performance culture that sees Enablement as a strategic lever – not a support function
• You’ll be empowered to bring a data-informed, behavior-focused approach to seller development
• Collaborate with peers in GTM Systems and Revenue Operations to create a unified revenue engine
• Work in a remote-first environment with a leadership team that values execution and autonomy

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.

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