[Hiring] Senior Content Specialist, Customer Education @Fleetio

Role Description

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.

• 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.

Qualifications

• 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.

Requirements

• 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.