Onboarding Specialist - Fleetio

Position Overview

As an Onboarding Specialist for Fleetio's Onboarding Services team, your primary responsibility is to ensure our customers achieve full adoption of our fleet management and maintenance software platform. This involves building strong relationships with key stakeholders and delivering a structured, process-driven onboarding experience. You will work directly with customers to:

• Document their desired outcomes.
• Provide product training.
• Configure their Fleetio account.
• Import their data.
• Facilitate the product rollout to their users.

In this role, you will manage a portfolio of onboarding projects across diverse customer industries and geographies. You will collaborate with and be supported by various Fleetio teams and integration partners to guide customers through their onboarding journey. We are seeking a highly organized, detail-oriented, and tech-savvy individual who excels at optimizing processes to help customers adopt new technology and develop successful habits.

About Fleetio

Fleetio is a modern software platform empowering thousands of organizations worldwide to manage their fleet operations. We are a leader in the transportation technology sector, experiencing significant growth with a strong customer base. In March 2025, we successfully closed our Series D funding round, securing $450 million, and are on an exciting growth trajectory. Fleetio is also a proud founding member of the Rails Foundation.

• Culture Videos: https://fleet.io/culture
• Fleetio Overview: https://www.youtube.com/watch?v=IlvIbwZT3oU
• Careers Page: https://www.fleetio.com/careers

Your Impact

• Collaborate closely with customers to assess their goals and existing business practices, ensuring onboarding alignment, proper account setup, and implementation support.
• Track tasks against project schedules, execute onboarding efforts, and coordinate with internal staff to meet milestones in a timely manner.
• Measure and track customer onboarding outcomes.
• Act as the voice of the customer, partnering with Engineering, Marketing, Product, and Sales teams to deliver a best-in-class customer experience.
• Become a trusted resource for software and productivity trends within the fleet management domain.

Your Experience

• A minimum of 3 years of experience in a customer-facing role within a SaaS environment, with a preference for experience in customer success or support with a focus on training or implementation.
• Familiarity with tools such as:
  • Project Management (e.g., Gainsight)
  • CRM systems (e.g., Salesforce)
  • Online Project Management tools (e.g., Asana)
  • Internal Communication tools (e.g., Slack)
• Strong proficiency in Excel, with the ability to manipulate and import large datasets.
• Impeccable written and verbal communication skills, with the ability to interact effectively with all levels of customers and build trust quickly.
• Meticulous and precise in task execution, demonstrating painstaking accuracy and thoroughness in details while managing time effectively.
• A strong team player with the ability to work autonomously as a self-starter.
• Empathetic and driven to help customers become natural Fleetio evangelists.
• Passionate about organization, with the ability to adhere to and improve organizational systems, identifying opportunities to reduce redundant work.
• Comfortable with change, experimentation, and adopting new ideas.

Benefits

• 100% dental and health coverage (50% for family).
• Vision insurance.
• Incentive stock options.
• 401(k) with a 4% match.
• 4 weeks of Paid Time Off (PTO).
• 12 company holidays plus 2 floating holidays.
• Parental leave: 16 weeks paid for birthing parents, 4 weeks for non-birthing parents.
• Flexible Spending Account (FSA) & Health Savings Account (HSA) options.
• Short-term and long-term disability insurance (short-term is 100% paid).
• Community service funds.
• Professional development funds.
• Wellbeing fund: $150 quarterly.
• Business expense stipend: $125 quarterly.
• Mac laptop and new hire equipment stipend.
• Monthly catered lunches.
• Fully stocked kitchen with a wide variety of drinks and snacks.
• Remote working friendly since 2012.