Head of GTM Enablement, Fleetio
+ Incentive Stock Options
Fleet management platform
Open for applications
Fleet management platform
201-500 employees
Open for applications
+ Incentive Stock Options
201-500 employees
Company mission
To help organizations track, analyze and improve their fleet operations.
Role
Who you are
- 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
- 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
What the job involves
- 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
- 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)
- 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
Our take
Fleetio offers software that helps organizations track, analyze, and improve their fleet operations. Fleet management is known to be an often complex and difficult task, so Fleetio's services unburden organizations of this, enabling them to focus time and energy on their own mission.
The company makes it easier for businesses to lease a fleet of vehicles with an app with which managers, drivers and mechanics can access and update information, relieving users of outdated fleet software and complicated spreadsheets. This simple solution has proven effective with the start-up seeing nearly 400% growth in a three year margin.
The company's had a successful 20215 too, having raised over $450M early in the year which also came with the acquisition of Auto Integrate. With moves like this, Fleetio can certainly expect to continue its growth, especially given its stable position in a market estimated to be worth $52.4 billion by 2027.
Kirsty
Company Specialist at Welcome to the Jungle
Insights
18% employee growth in 12 months
Company
Funding (last 2 of 5 rounds)
Mar 2025
$450m
SERIES D
May 2023
$144.7m
SERIES C
Total funding: $620m
Company benefits
- Health & Wellness: Taking care of you and your family is important to us. Our healthcare plans deliver choice and value so you can prioritize your health
- 401k Match: Plan for your future. We match your retirement contributions up to 4% of your salary each pay period
- PTO/Holidays: Four weeks of paid time off (PTO), two floating holidays, as well as 12 company holidays
- Parental Leave: We provide all our team members (birthing & non-birthday parents) time off to care for and bond with their newborn or newly adopted children
- Stock Options: At Fleetio, we grant all our team members options to acquire an ownership stake in Fleetio
- Professional Development: Team members get an annual professional development allowance to invest in their own professional growth
Company HQ
Central City, Birmingham, AL
Leadership
Jon Meachin
(CEO)Jon initially joined Fleetio as COO in 2022, becoming CEO in 2023. Prior to this, they were COO at A Cloud Guru and held VP roles at Campaign Monitor and McKissock.
Matthew Mandel
(CFO/COO)Prior to joining Fleetio in 023, Matthew was the COO and Co-CEO at Cometeer. They also spent 3 years at Wayfair in various General Manager roles.
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