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

Fleetio provides equal employment opportunities to all employees and applicants and prohibits discrimination and harassment. We celebrate diversity and are committed to creating an inclusive environment for all. All employment is decided on the basis of qualifications, merit, and business need.

This application is not intended to and does not create a contract or offer of employment. Employment with Fleetio is at will.

If you have a disability or a special need that requires accommodation to fill out the online application, please let us know by calling (205) 718-7500 or emailing recruiting@fleetio.com.