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Remote Observability Engineer Jobs in Chicago, IL

CFS

AI Engineer

Chicago, IL · Remote

$200K/yr

Remote * PTO: Unlimited * Retirement: 401K w/ a match * Medical: Health, vision, and dental plans ... Build comprehensive testing frameworks, observability tooling, and diagnostic systems for agent ...

CFS

AI Engineer

Chicago, IL · Remote

$200K/yr

Remote * PTO: Unlimited * Retirement: 401K w/ a match * Medical: Health, vision, and dental plans ... Build comprehensive testing frameworks, observability tooling, and diagnostic systems for agent ...

CFS

AI Engineer

Chicago, IL · Remote

$200K/yr

Remote * PTO: Unlimited * Retirement: 401K w/ a match * Medical: Health, vision, and dental plans ... Build comprehensive testing frameworks, observability tooling, and diagnostic systems for agent ...

CFS

AI Engineer

Chicago, IL · Remote

$200K/yr

Remote * PTO: Unlimited * Retirement: 401K w/ a match * Medical: Health, vision, and dental plans ... Build comprehensive testing frameworks, observability tooling, and diagnostic systems for agent ...

iManage

DevOps Engineer

Chicago, IL · On-site +1

$54.50 - $74.50/hr

Mondays and Fridays are reserved for (remote-friendly) focus time to get things done. Have the best ... You'll be a key voice in observability, change management, and service scalability. iManage is ...

G2i Inc.

DevOps Engineer

Chicago, IL · Remote

$54.50 - $74.50/hr

Remote (US based, US citizens only) Type: Full-Time What You'll Do: * Infrastructure: Own and ... Monitoring & Observability: Set up alerting, log aggregation, and performance dashboards (e.g ...

CFS

AI Engineer

Chicago, IL · Remote

$200K/yr

Remote * PTO: Unlimited * Retirement: 401K w/ a match * Medical: Health, vision, and dental plans ... Build comprehensive testing frameworks, observability tooling, and diagnostic systems for agent ...

CFS

AI Engineer

Chicago, IL · Remote

$200K/yr

Remote * PTO: Unlimited * Retirement: 401K w/ a match * Medical: Health, vision, and dental plans ... Build comprehensive testing frameworks, observability tooling, and diagnostic systems for agent ...

CFS

AI Engineer

Chicago, IL · Remote

$200K/yr

Remote * PTO: Unlimited * Retirement: 401K w/ a match * Medical: Health, vision, and dental plans ... Build comprehensive testing frameworks, observability tooling, and diagnostic systems for agent ...

Origami Risk LLC

Site Reliability Engineer

Chicago, IL · On-site +1

$100K - $120K/yr

Maintains and configures core observability tools to ensure optimum performance and key metrics ... All full-time positions are hybrid, with many eligible to be completely remote * Fully Paid by ...

Relativity

Senior Software Engineer

Chicago, IL · On-site +1

$126.30K - $166.50K/yr

Posting Type Hybrid/Remote Job Overview WHO WE ARE Relativity is a leading legal data intelligence ... Champion security, quality, observability, and DevOps workflows to ensure performance and ...

Relativity

Senior Software Engineer

Chicago, IL · On-site +1

$126.30K - $166.50K/yr

Posting Type Hybrid/Remote Job Overview WHO WE ARE Relativity is a leading legal data intelligence ... Troubleshoot and resolve complex production issues using modern observability and debugging ...

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All JobsRemote Observability Engineer JobsRemote Observability Engineer Jobs in Chicago, IL

Remote Observability Engineer information

See Chicago, IL salary details

$39.1K

$119.4K

$197.3K

How much do remote observability engineer jobs pay per year?

As of May 28, 2026, the average yearly pay for remote observability engineer in Chicago, IL is $119,357.00, according to ZipRecruiter salary data. Most workers in this role earn between $85,500.00 and $156,100.00 per year, depending on experience, location, and employer.

What are the key skills and qualifications needed to thrive as a Remote Observability Engineer, and why are they important?

To thrive as a Remote Observability Engineer, you need strong expertise in monitoring, logging, and tracing systems, along with a background in computer science or related technical fields. Familiarity with tools like Prometheus, Grafana, ELK Stack, Datadog, and cloud platforms is typically required, as well as relevant certifications such as AWS Certified Cloud Practitioner or Google Cloud Professional DevOps Engineer. Excellent problem-solving abilities, communication skills, and a proactive mindset help you detect and resolve issues before they impact users. These competencies ensure system reliability, enable rapid incident response, and support seamless collaboration in distributed environments.

What are the typical collaboration patterns for a Remote Observability Engineer working with distributed teams?

Remote Observability Engineers frequently collaborate with software developers, DevOps teams, and IT operations to ensure systems are monitored effectively and issues are detected early. Working remotely, you'll often use communication tools like Slack, Jira, and video conferencing to coordinate incident response, discuss monitoring strategies, and review system health dashboards. Regular sync meetings and asynchronous updates are common, and you'll likely contribute to documentation and knowledge sharing to keep all stakeholders informed. Building strong communication habits is important, as much of the troubleshooting and improvement work hinges on clear coordination with multiple teams.

What is a Remote Observability Engineer?

A Remote Observability Engineer is a professional responsible for designing, implementing, and maintaining systems that monitor the health, performance, and reliability of software applications and infrastructure from a remote location. They use observability tools to collect and analyze logs, metrics, and traces, helping organizations quickly detect and resolve issues. Their work ensures that distributed systems are transparent, reliable, and efficient, often collaborating with development, operations, and security teams. Remote Observability Engineers often work from anywhere, leveraging cloud-based tools and platforms to manage complex IT environments.

What is the difference between Remote Observability Engineer vs Site Reliability Engineer?

AspectRemote Observability EngineerSite Reliability Engineer
CredentialsKnowledge of monitoring tools, scripting, cloud platformsSame as Observability Engineer, plus SRE certifications often preferred
Work EnvironmentFocus on monitoring, logging, and tracing systems remotelyBroader scope including system reliability, incident response, and automation
Industry UsagePrimarily in tech, SaaS, cloud servicesWidely in tech, finance, and large-scale online services

The Remote Observability Engineer specializes in monitoring and analyzing system performance remotely, focusing on tools like logs and metrics. In contrast, the Site Reliability Engineer has a broader role, ensuring overall system reliability, automation, and incident management. While both roles require similar technical skills, SREs often have additional responsibilities related to system resilience and scalability.

What are the most commonly searched types of Observability Engineer jobs in Chicago, IL? The most popular types of Observability Engineer jobs in Chicago, IL are:
What are popular job titles related to Remote Observability Engineer jobs in Chicago, IL? For Remote Observability Engineer jobs in Chicago, IL, the most frequently searched job titles are:
What job categories do people searching Remote Observability Engineer jobs in Chicago, IL look for? The top searched job categories for Remote Observability Engineer jobs in Chicago, IL are:
What cities near Chicago, IL are hiring for Remote Observability Engineer jobs? Cities near Chicago, IL with the most Remote Observability Engineer job openings:
Remote Observability Engineer jobs near you
Infographic showing various Remote Observability Engineer job openings in Chicago, IL as of May 2026, with employment types broken down into 91% Full Time, 6% Part Time, and 3% Contract. Highlights an 87% Physical, 1% Hybrid, and 12% Remote job distribution, with an average salary of $119,357 per year, or $57.4 per hour.

AI Engineer

CFS

Chicago, IL • Remote

$200K/yr

Full-time

Medical, Dental, Vision, Retirement, PTO

Posted 27 days ago

Job description

AI Engineer | Permanent | No Sponsorship Available | Remote

BENEFITS & COMPENSATION

  • Compensation: Up to $200,000 per year + 8% annual bonus target
  • Work Environment: Remote
  • PTO: Unlimited
  • Retirement: 401K w/ a match
  • Medical: Health, vision, and dental plans available for individuals and families

AI ENGINEER
JOB RESPONSIBILITIES

  • Partner with stakeholders to identify high-impact opportunities where AI can drive efficiency, growth, and competitive advantage
  • Design and deploy sophisticated LLM-based agent systems, reasoning workflows, and tool-integrated pipelines (RAG, chain-of-thought, planning-execution patterns)
  • Architect and maintain production-grade APIs supporting real-time and asynchronous agent operations, including Model Context Protocol (MCP) integration
  • Develop robust prompt strategies, vector database implementations, and knowledge graph architectures ensuring reliable model behavior
  • Build comprehensive testing frameworks, observability tooling, and diagnostic systems for agent execution and performance monitoring
  • Manage the complete AI model lifecycle—integration, deployment, fine-tuning, and production monitoring with logging and recovery mechanisms
  • Establish AI governance standards addressing compliance, security, responsible AI, and ethical considerations
  • Champion AI adoption across the organization; define success metrics, track progress, and drive organizational alignment
  • Collaborate with frontend teams to build intuitive user interfaces and seamless AI system integration using React and TypeScript

AI ENGINEER
QUALIFICATIONS

  • 10+ years of software development and systems architecture experience
  • 3+ years of hands-on experience designing and implementing AI-driven solutions with production AI tools
  • 3+ years of specialized expertise with Large Language Models, Generative AI, NLP, and machine learning fundamentals
  • Practical experience with deep learning frameworks, RAG architectures, vector databases, and agent-based frameworks
  • Working knowledge of cloud-native AI services and deployment patterns

Build a rewarding long-term career with us at CFS—when we knock, doors open.
Timing is everything. Whether you are aggressively in a job search or simply passive and looking for the ideal position, we would like to have the chance to share our opportunities with you. We specialize in placement of IT professionals. Please contact me for more information about this role as well as other opportunities.

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