GTM Onboarding Manager

A little about us…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 every day. We raised $450M in our Series D funding round in March of 2025 and are on an exciting trajectory as a company. Fleetio is also a proud founding member of the Rails Foundation!

More about our team and company:

• Fleetio overview video: https://www.youtube.com/watch?v=YoXyXTFWbkg
• Our careers page: https://www.fleetio.com/careers

About the role

The GTM Onboarding Manager sits on the GTM Enablement team and owns the end-to-end onboarding experience for our Go-To-Market organization, with equal focus on Sales and Client Experience (CX). You will design and run a virtual-first, tech-forward onboarding program that ramps new hires quickly and builds confidence in-role through structured learning, practice, and manager coaching.

This role is ideal for someone who has been customer-facing (especially in Sales or CX) or has supported customer-facing teams closely, and can translate “what it takes to win” into repeatable onboarding and ongoing development. You’ll also use AI and automation to make onboarding scalable, consistent, and easy for new hires and managers to navigate especially for early-career learners.

What you’ll do

Build and run a best-in-class onboarding program for Sales + CX

• Own the 30/60/90 onboarding journeys for key GTM roles (e.g., AEs/AMs/SDRs/SCs and CX roles such as Implementation, CSM, Support, and leaders).
• Create role-based readiness gates (knowledge + skill) with clear “graduation” standards for both Sales and CX.
• Partner with Sales and CX leaders to define what “good” looks like in the first 90 days, including manager coaching responsibilities and inspection rhythms.
• Design onboarding for an early-career demographic, meeting learners where they are with structured paths, confidence-building practice, and clear expectations.

Deliver virtual-first enablement using technology

• Facilitate live and on-demand onboarding sessions, workshops, and practice sessions (role plays, scenarios, labs) in a virtual environment.
  Use technology to create an engaging learning experience and build reusable assets for learning and reinforcement.
• Build role-based learning paths that are easy to find, easy to follow, and continuously reinforced.

Scale onboarding with AI and automation

• Build a scalable onboarding engine by automating repeatable workflows (preboarding checklists, scheduling, reminders, nudges, completion tracking, manager tasks, and readiness sign-offs).
• Create an AI-enabled “on-demand” onboarding experience that supports new hires and managers with just-in-time guidance (e.g., where to find resources, how to execute key workflows, how to prepare for calls/customer moments).
• Use AI to accelerate content creation and maintenance (e.g., roleplay scenarios, call/ticket practice prompts, knowledge checks), while ensuring quality and alignment to approved source material.

Measure and improve outcomes

• Track onboarding performance across Sales and CX
• Partner with RevOps / Analytics to connect onboarding to outcomes (pipeline/productivity signals for Sales; adoption/health signals for CX)
• Iterate programs using data, leader feedback, and learner input.

What success looks like

• New hires in Sales and CX ramp faster and hit role milestones sooner.
• Managers in both orgs consistently coach onboarding expectations with clear tools and cadence.
• Onboarding is a smooth, repeatable, virtual-first experience with high satisfaction.
• AI and automation reduce manual effort and improve consistency (e.g., higher self-serve resolution, faster updates, fewer “where do I find/how do I do” questions, measurable adoption of on-demand support).
• Everboarding improves execution consistency and keeps teams aligned as the business evolves.

What we’re looking for

Required

• 5+ years either in a customer-facing role (Sales or CX strongly preferred) or supporting a customer-facing organization (sales enablement, CX enablement, revenue operations, GTM programs) with demonstrated practical acumen.
• 2+ years owning or delivering onboarding/enablement programs (virtual-first) for Sales and/or CX.
• Proven ability to facilitate live sessions, run practice sessions, and coach skills.
• Strong program management: planning, stakeholder alignment, and delivery.
• Comfort using technology to run programs (LMS, content hubs, enablement tools, Zoom-style facilitation).
• Demonstrated ability to leverage AI and automation to scale enablement/onboarding (e.g., workflow automation, self-serve support, AI-assisted content development, or AI-enabled practice/reinforcement).

Nice to have

• Experience building readiness gates/certifications and competency frameworks.
• Experience with GTM operating cadences (Sales: forecasting, deal reviews, territory planning, QBRs; CX: health/risk inspection, escalation rhythms, adoption planning).
• Experience coaching leaders or managers (coach-the-coach programs, inspection cadences, call/deal coaching frameworks).
• Experience in B2B SaaS and supporting a scaled GTM org.
• AI-assisted knowledge support (strong governance and source-of-truth discipline).
• Career pathing, role scoping, and proficiency expectations (competencies and levels) development.

Key skills

• Facilitation, coaching, and presence (virtual and live).
• Strong customer-facing acumen.
• Learning design familiarity.
• Stakeholder management and influence without authority.
• Data-driven mindset and continuous improvement.
• AI + automation fluency (practical use to scale onboarding, not just experimentation).
• Systems thinking (designing repeatable processes that work as the business changes).

Benefits 

• Multiple health/dental coverage options (100% coverage for employee, 50% for family)
• Vision insurance
• Incentive stock options
• 401(k) match of 4%
• PTO - 4 weeks (increases at year two!)
• 12 company holidays + 2 floating holidays
• Parental leave - birthing parent (16 weeks paid) non-birthing (4 weeks paid)
• FSA & HSA options
• Short and long term disability (short term 100% paid)
• Community service funds
• Professional development funds
• Wellbeing fund - $150 quarterly
• Business expense stipend - $125 quarterly
• Mac laptop + new hire equipment stipend
• Fully stocked kitchen with tons of drinks & snacks (BHM only)
• 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 an accommodation to fill out the online application, please let us know by calling (205) 718-7500.