Senior Site Reliability Engineer

Wwshemi; Northern (KY); Remote; USD 120,000 - 180,000; Full time

Benefits offered by this job

Health insurance

Dental coverage

Vision insurance

401(k) match

PTO - 4 weeks

Generous holidays

Remote-friendly culture

Professional development funds

Job summary

Fleetio is seeking a Senior Site Reliability Engineer to scale our Ruby on Rails stack and infrastructure. You will improve performance, observability, and reliability while integrating AI-driven workflows.

This remote role is open to candidates in the United States and involves on-call duties and collaboration with a fast-paced Platform Engineering team. You will mentor teams, lead database capacity and DR planning, and help build AI agents to reduce toil across incident response and

Qualifications

• 5+ years of Ruby/Rails experience.
• 3+ years of AWS experience.
• Kubernetes familiarity and observability tooling.
• Experience with Datadog or similar APM tools.
• Strong problem solving and communication skills.

Responsibilities

• Identify and resolve performance issues.
• Improve observability across Rails, Ruby and databases.
• Build AI agents and automations to reduce toil.
• Lead capacity planning and DR planning.
• Collaborate with SREs and engineers on reliability.

Skills

Ruby/Rails

AWS

Kubernetes

profiling

Datadog/APM

Code review

AI/automation

Observability

Tools

Kafka

Redis

Elasticsearch

TimescaleDB

Terraform

Job description

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 (https://rubyonrails.org/foundation)!

More about our team and company:

• Fleetio overview video: https://www.youtube.com/watch?v=YoXyXTFWbkg (https://www.youtube.com/watch?v=YoXyXTFWbkg)

• Our careers page: https://www.fleetio.com/careers (https://www.fleetio.com/careers)

Description

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.

More About Our Team and Company

• Watch our culture videos: https://fleet.io/culture (https://fleet.io/culture)

• Engineering culture, interview process and videos: https://www.fleetio.com/careers/engineering (https://www.fleetio.com/careers/engineering)

• Fleetio Go overview video: https://www.fleetio.com/go (https://www.fleetio.com/go)

• More about the Fleetio platform: https://www.fleetio.com/features (https://www.fleetio.com/features)

• API docs: developer.fleetio.com (https://developer.fleetio.com/)

• Test drive Fleetio to get an even better feel for what we're building: https://www.fleetio.com/register (https://www.fleetio.com/register)

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

• 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 [phone].