Head of GTM Enablement, Fleetio
+ Incentive Stock Options
Fleet management platform
Be an early applicant
Fleet management platform
201-500 employees
Be an early applicant
+ 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, analyse, 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 start-up 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 planned to invest its funding towards expanding operations and venturing into new markets globally, as well as developing new services. In 2023, it integrated with FleetIT and Toll Management Solutions to offer nationwide coverage for fleets at reduced rates. 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
- 100% health/dental coverage (50% family)
- Vision insurance
- Incentive stock options
- 401(k) match of 4%
- PTO - 4 weeks
- Parental and bonding leave
- 8 company holidays + 2 floating holidays
- Dependent care and medical FSA
- Community service funds
- Short and long term disability
- Mac laptop + new hire equipment stipend
- Professional development funds
- Health and wellness initiatives
- Remote working friendly
- Monthly catered lunches
- Office snacks
Company HQ
Central City, Birmingham, AL
Leadership
Tony Summerville
(CEO)Previously served as Product Manager for Daxko and as a Software Engineer for Regions Financial Corporation. Currently acts as a Board Member for TechBirmingham and Venture for America.
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