Senior Site Reliability Engineer - Fleetio

About Fleetio

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!

About the Role

Our Platform Engineering team is looking for a Senior Site Reliability Engineer to help run, maintain, and improve the performance of our Ruby on Rails Stack and Infrastructure. You will help scale our application using best in class architecture and software design. This includes training, software engineering, system design, and operational practices that support the needs of our engineers and customers while accounting for future growth. You will be entrusted with proactively identifying and owning initiatives that will help improve the performance, reliability, and scalability of our application stack and databases.

Our team treats AI as a core part of how we engineer. We build and use AI agents, skills, and automated workflows to handle toil, speed up investigation and remediation, and give our engineers more time for high-leverage work.

This is a remote opportunity and is open to candidates in the United States.

Who You Are

Our ideal candidate is an Infrastructure Engineer experienced in scaling Ruby on Rails applications, with a passion for optimization and performance improvements. You bring a strong background in Site Reliability and Infrastructure Engineering for Rails applications. You follow Agile and DevOps principles, can effectively influence teams to achieve goals, and demonstrate excellent problem-solving skills in our fast-paced environment.

You're curious about how AI is changing infrastructure and reliability work, and you're eager to shape how a platform team puts it to use.

Your Impact

As a Senior Site Reliability Engineer on Fleetio's Platform Engineering team, you will:

• Proactively identify, triage, and resolve performance issues
• Enhance system observability by monitoring performance metrics across Ruby, Rails, and database systems, including SLOs and SLIs
• Build and maintain AI agents, skills, and automations that reduce operational toil across incident response, triage, and routine maintenance
• Use AI-assisted tooling to accelerate performance analysis, root-cause investigation, and code review
• Collaborate with other SREs to proactively identify and address performance bottlenecks
• Help product engineers adopt AI-driven workflows for performance and reliability best practices
• Lead database capacity planning and upgrade initiatives
• Manage the database-specific components of disaster recovery planning and execution
• Oversee backup systems and pre-production databases
• Create and maintain infrastructure and operations documentation, including runbooks and context that both engineers and AI agents can act on
• Participate in the on-call rotation

Your Experience

• 5+ years of Ruby/Rails Experience
• 3+ years of AWS Experience
• Kubernetes experience
• Experience with profiling and benchmarking source code
• Effective at code review and identifying potential performance problems before they reach production
• Experience with Datadog or other APM tools
• Excellent written and verbal communication skills

Considered a Plus

• Experience building AI agents, LLM-powered automations, or integrations (e.g., using tool/function calling or MCP) for engineering or operations workflows
• Infrastructure as Code tools (Terraform)
• Deep understanding of cloud network fundamentals (routing, firewalls, load balancers, CDNs, VPCs, etc.)
• Experience with distributed event and data stores, such as Kafka, Redis, Elasticsearch, Memcached, and TimescaleDB
• You know a thing or two about the fleet management industry

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
• Remote working friendly since 2012