Senior Observability Engineer – Cloud & Dynatrace

Chamberlain Advisors; Deerfield (IL); Remote; Full time

Job summary

Chamberlain Advisors is seeking a Senior Observability Engineer to define and standardize observability practices across a complex cloud ecosystem. This role focuses on developing scalable monitoring solutions using Dynatrace and guiding various teams on observability strategy. Ideal candidates will have deep cloud infrastructure expertise and software engineering fluency, driving operational visibility in a cross-functional environment.

Benefits

Healthcare Insurance

Dental Insurance

Qualifications

• 8+ years of experience in observability, DevOps, or cloud engineering roles.
• Advanced hands-on expertise with Dynatrace, including certification preferred.

Responsibilities

• Design and implement enterprise-wide observability frameworks leveraging Dynatrace.
• Guide internal teams on observability onboarding and conduct workshops.

Skills

Performance Engineering

Telemetry Instrumentation

Monitoring-as-Code

Problem-Solving

Education

Bachelor’s degree in Computer Science

Tools

Dynatrace

Azure

Terraform

Jenkins

GitHub Actions

Azure DevOps

Job description

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Title: Senior Observability Engineer – Cloud & Dynatrace

Location: Open to Remote (Preference for candidates local to Deerfield, Chicago, IL if converted to FTE)

Duration & Type: 6-Month Contract (Potential Contract-to-Hire)

Compensation: Competitive W2 Hourly Rate ($76-$78), Access to Healthcare and Dental Insurance Plan of Choice. (Benefit Plans can be requested at time of submission to client)

Summary

Chamberlain Advisors is seeking a Senior Observability Engineer (Cloud) to define, implement, and standardize enterprise-wide observability practices across a complex cloud ecosystem. This high-impact role is responsible for developing scalable, full-stack monitoring solutions using Dynatrace, guiding the observability strategy across DevOps, product, platform, and security teams. The ideal candidate combines deep cloud infrastructure expertise with software engineering fluency and a strong understanding of monitoring and performance optimization principles. As part of a strategic transformation initiative, this role will own the design and onboarding process for observability frameworks, lead internal reviews, and establish governance for performance metrics, alerting, and telemetry standards across the enterprise. This is an exciting opportunity for a candidate who thrives in a cross-functional environment and is passionate about driving best-in-class operational visibility. Click Apply Now to join the Chamberlain experience.

What You’ll Be Accountable For

• Design and implement enterprise-wide observability frameworks and standards leveraging Dynatrace
• Serve as subject matter expert on performance engineering, telemetry instrumentation, and monitoring-as-code
• Guide internal teams on observability onboarding, conducting workshops, engineering reviews, and mentoring sessions
• Define architecture standards for cloud observability within Azure, partnering with engineering, cloud ops, and security
• Collaborate with platform, product, and compliance teams to align monitoring strategy with business and regulatory requirements
• Identify performance, availability, and reliability risks and propose proactive observability solutions
• Support proof-of-concept development and the evaluation of new observability solutions or enhancements
• Ensure adoption of observability-as-code principles via IaC tools and modern CI/CD pipelines
• Facilitate data-driven decision-making by ensuring effective telemetry, alerting, and dashboard design
• Lead the transformation from traditional monitoring to proactive, predictive observability models
  
  

What Qualifications You Need

• Bachelor’s degree in Computer Science, Engineering, or a related technical field
• 8+ years of experience in observability, DevOps, or cloud engineering roles
• Advanced hands-on expertise with Dynatrace, including certification preferred
• Strong experience with Azure cloud environments, including Azure observability tooling
• Expertise in Infrastructure-as-Code (IaC) and CI/CD tooling such as Terraform, Bicep, Jenkins, GitHub Actions, or Azure DevOps
• Proven success designing and operationalizing full-stack observability strategies for large-scale environments
• Familiarity with SRE principles, logging/metrics/tracing frameworks, and telemetry standards (OpenTelemetry, Prometheus, etc.)
• Ability to communicate and collaborate with engineers, product owners, executives, and compliance teams
• Experience building observability solutions for both distributed microservices and legacy monolith applications
• Strong problem-solving skills and the ability to operate independently in a highly matrixed organization
• Demonstrated ability to plan and lead observability reviews, workshops, and engineering onboarding sessions
• Familiarity with governance and compliance frameworks that influence monitoring strategies
  
  

About The Client

Our fortune 20 client is seeking innovative and intelligent individuals to join their team. Here is your opportunity to join one of the largest healthcare and retail pharmacy companies in the U.S, with more than 10 million customers, over 8,000 retail stores, and a presence in multiple countries. Our client is constantly creating groundbreaking ways to meet customer needs, improve their health, and be a force for good in the world. This is your chance to work in a truly supportive environment and be a part of a progressive organization dedicated to the well-being of their customers, team members, and communities.

Why Work with Chamberlain?

Chamberlain Advisors is a veteran-owned business that provides human capital solutions through contract, contract-to-hire, direct-hire, and retained-search opportunities. Chamberlain candidates benefit from our unique hiring and interviewing process which has been designed to increase the likelihood that they will be successful in their job searches. This is achieved through our 5-step recruitment process, ensuring a top-of-the-line candidate experience. Find out what makes us different; apply to Chamberlain today.

Equal Employment Opportunity

Chamberlain Advisors provides equal employment opportunities (EEO) to all employees and applicants for employment without regard to race, color, religion, sex, national origin, age, disability, or genetics. In addition to federal law requirements, Chamberlain Advisors complies with applicable state and local laws governing nondiscrimination in employment in every location in which the company has facilities. This policy applies to all terms and conditions of employment, including recruiting, hiring, placement, promotion, termination, layoff, recall, transfer, leaves of absence, compensation, and training.

Chamberlain Advisors expressly prohibits any form of workplace harassment based on race, color, religion, gender, sexual orientation, gender identity or expression, national origin, age, genetic information, disability, or veteran status. Improper interference with the ability of Chamberlain Advisors' employees to perform their job duties may result in discipline up to and including discharge.

Seniority level

• Seniority level

  Mid-Senior level

Employment type

• Employment type

  Contract

Job function

• Job function

  General Business, Information Technology, and Consulting

• Industries

  Staffing and Recruiting

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