Senior Content Specialist, Customer Education

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:
Our careers page: 
We're looking for a Senior Content Specialist who will play an important role in ensuring Fleetio’s customers have a comprehensive understanding of our product. We believe education is key to our customers’ success. We are looking for a passionate and dedicated individual to join our team to help ensure our customers are well-equipped to succeed using Fleetio.
Your Impact
Create and maintain clear, approachable documentation and product walkthroughs that empower customers to learn and solve problems on their own
Own and evolve our knowledge management platform, keeping our internal and external knowledge bases polished, easy to navigate, and up-to-date
Partner with the Manager, Customer Education to ensure content aligns with our broader education strategy
Run documentation sprints, making sure the right work is prioritized, assigned, and shipped on time
Work closely with Customer Support to reduce case volume through better knowledge, smarter content, and AI-powered solutions
Collaborate with Customer Education and CX teams to shape our internal documentation strategy, including roadmap planning and scalable review processes
Keep a pulse on what’s working (and what’s not) by tracking trends, sharing insights, and driving continuous improvement
Proactively identify knowledge gaps by analyzing support trends, product changes, and customer feedback
Support larger education initiatives like webinars, community programming, and LMS content
Use data to understand how customers engage with our content and where we can improve
Bring forward ideas and recommendations to make our Customer Education programs even better
Your Experience
5+ years of experience creating and managing customer-facing content in a SaaS environment, especially technical product documentation
A knack for turning complex ideas into simple, helpful content that works for a variety of audiences
Strong writing and editing skills with a sharp eye for clarity and detail
Clear, effective communication, both written and verbal
Comfort using AI tools and automation to work smarter and move faster
A deeply customer-first mindset—you care about getting people the right information at the right time
Strong project management skills, with the ability to juggle priorities and collaborate across teams in a fast-moving environment
Considered a plus
Previous Fleet or Fleet Software Experience
Past experience using Helpjuice or other technical documentation tools
Video production & editing experience
Community or customer webinar experience
Experience with Camtasia, Arcade, Wistia or similar systems
Past experience using Asana or similar project management tool
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.