Site Reliability Engineer / Azure / Chicago / Remote

A rapidly growing, U.S.-based SaaS company in the legal tech space is seeking a Senior Site Reliability Engineer to join their fully remote team. This is a full-time, direct-hire opportunity with a company recognized nationally for innovation and growth. You'll be joining a well-funded tech organization building cloud-native solutions at scale, with a strong focus on reliability, automation, and developer experience.

This isn't just an ops role—it's a chance to engineer intelligent, autonomous systems that keep high-scale software reliable, performant, and secure. This company is modernizing the way professionals work and is building a best-in-class reliability team to support that mission. You’ll work on greenfield automation, shape engineering standards, and collaborate closely with development teams. If you're passionate about observability, automation, and infrastructure as code, this is a fantastic opportunity to own mission-critical systems and grow your personal brand as a top-tier engineer—all while enjoying full remote flexibility and a healthy work-life balance.
Required Skills & Experience

• 8+ years in technical roles, with at least 2+ years of SRE experience
• Strong scripting with Python, Bash, or Powershell
• Proven experience building autonomous systems for software reliability
• Experience with CI/CD pipelines and infrastructure automation
• Strong understanding of observability, monitoring, and alerting systems
• Bachelor’s degree in Computer Science or related field—or equivalent experience

Desired Skills & Experience

• 2–6 years of focused SRE experience
• Experience with highly available, internet-scale systems
• Exposure to AI/ML integration in production environments
• Master’s degree or relevant certifications

What You Will Be Doing
Tech Breakdown

• 40% – Scripting & automation (Python, Bash, Powershell)
• 30% – CI/CD pipeline tooling & infrastructure (GitHub Actions, Terraform, etc.)
• 30% – Monitoring, alerting, observability systems (Datadog, Grafana, etc.)

Daily Responsibilities

• 30% – Building autonomous systems to manage deployments and scaling
• 30% – Partnering with product and engineering teams on reliability improvements
• 20% – Developing internal tooling and improving operational workflows
• 20% – Participating in on-call rotation, incident response, and mentoring

The Offer

• Bonus eligible

You will receive the following benefits:

• Medical, Dental, and Vision Insurance
• Vacation Time
• Stock Options