[Hiring] Director of Customer Support at Fleetio

We’re seeking a forward-thinking, data-driven Director of Support to lead our global support function and deliver truly proactive, customer-inspired support experiences. You’ll collaborate closely with the GTM Systems team to evolve our support tooling strategy and play a key role in shaping how our customers engage with us.

In this role, you’ll champion the voice of the customer and use support trends to influence product innovation and business decisions, working cross-functionally with Package, Engineering, Customer Education, Customer Success, and GTM Systems to ensure that support insights are translated into action—enhancing both customer satisfaction and our ability to scale.

A little about us… Fleetio is a modern software platform that helps thousands of organizations around the world 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 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:

• Watch our culture videos: https://fleet.io/culture
• Fleetio overview video: https://www.youtube.com/watch?v=IlvIbwZT3oU
• Our careers page: https://www.fleetio.com/careers

Your Impact

• Lead and scale a high-performing, globally distributed support team that aligns with our values of empathy, curiosity, and continuous improvement.
• Develop and own a support tooling strategy that enables scalable, proactive, and personalized support experiences—leveraging AI, automation, and integrations.
• Use support trend data and voice-of-customer insights to influence product development, identify gaps, and co-create enhancements with Package and Engineering.
• Drive initiatives to improve self-service adoption, including knowledge base development, in-app guidance, and customer education resources.
• Define and monitor key support KPIs (e.g. CSAT, FRT, resolution time, ticket deflection), using them to guide strategy and resource allocation.
• Own the hiring strategy, enabling us to grow and scale a diverse team of fleet software experts aligned to our company’s growth
• Foster a culture of continuous feedback and coaching, enabling team growth and high performance in a dynamic, fast-paced environment.
• Own the selection, implementation, and optimization of support technologies and platforms (e.g., Zendesk, Intercom, Salesforce).
• Ensure exceptional support during major releases, product changes, and incident response situations.
• Partner with Enablement to ensure our Support team members are the experts on our latest product enhancements and fleet trends.
• Collaborate with Onboarding, Customer Success, Customer Education, Partnerships, Package & Engineering, and Enablement to deliver a seamless customer experience across all touchpoints.

Your Experience

• 7+ years of experience in SaaS support roles, with 3+ years in a senior leadership position.
• Proven track record of designing and executing support strategies that scale with high-growth SaaS companies.
• Experience in managing support teams across multiple time zones or regions.
• Proven experience managing and communicating effectively with a diverse customer base, understanding the unique needs and expectations of each customer type.
• Demonstrated experience in turning support insights into product innovations that enhance the customer experience and drive growth.
• Deep knowledge of support tooling, CRM systems, and automation platforms—with a strategic mindset toward tool selection and integration.
• Strong data analysis skills—comfortable leveraging support metrics to drive decisions and improvements.
• Excellent communication, coaching, and cross-functional collaboration skills.
• Passion for delivering customer-inspired experiences that reflect Fleetio’s values of Intelligence, Intensity, Integrity, and Ownership.

Bonus Points

• Experience in the fleet industry.
• Familiarity with tools like Salesforce Service Cloud and Heap.
• Experience in customer experience operations as an analyst or system admin for support tooling.

Benefits

• Multiple health/dental coverage options (100% employee cost coverage; 50% cost coverage for family)
• Vision insurance
• Incentive stock options
• 401(k) match of 4%
• PTO – 4 weeks
• 12 company holidays + 2 floating holidays
• Parental leave- birthing parent (16 weeks paid) non-birthing (4 weeks)
• 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
• 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.