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Lessen LLC

Senior DevOps Engineer I

Sorry, this job was removed at 04:20 a.m. (CST) on Wednesday, Oct 29, 2025
Hybrid
Chicago, IL, USA
Hybrid
Chicago, IL, USA

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Lessen is the tech-enabled, end-to-end property service provider that is transforming how commercial and residential real estate services are delivered and managed at scale. Lessen’s technology platform provides data-driven insights that unlock key growth opportunities for the entire real estate ecosystem—including investors, owners, managers, and service providers. The company leverages a network of over 30,000 vetted, qualified vendors (Lessen Affiliates) serving clients with over 1 million properties and completing more than 3.5 million work orders annually across an expanding range of services. Lessen, LLC is a venture-backed, privately held company with offices in Scottsdale and Chicago. 

Summary
The Senior DevOps Engineer I supports the Product and Technology Department by developing and building IT solutions, installing and configuring solutions, and implementing reusable components. They will also translate technical requirements, assist with all stages of test data, develop interface stubs and simulators, and perform script maintenance and updates.

Responsibilities
· Recommend alternate choices and trade-offs for various design decisions; investigate performance and process failures and work to improve them.
· Developing and build IT solutions, install and configure solutions, implement reusable components, translate technical requirements, and assist in all stages of the software development cycle.
· Stay apprised of new developments in both Azure and AWS cloud operations and help in determining architectural solutions to enhance the stability and performance of the infrastructure.
· Gain a deep application-level knowledge of the systems as well as contributing to their overall design.
· Work closely with other internal teams to build security, reliability, and scalability into the development lifecycle.
· Dive deep into the software stack to troubleshoot as needed and in resolving Windows and Linux operating system issues.
· Be on call as a part of rotating support schedule and respond to production issues and incidents in a timely manner.
· Build engineering automation and productivity tools to streamline and scale applications in the production environment.
· Build from the ground up reliable infrastructure services in AWS and Azure to deliver highly scalable services.
· Automate cloud operations using Infrastructure as Code tools and Configuration management tools.
· Ensures the confidentiality of internal and external data
· Performs ad-hoc projects and other duties as assigned
Role Specific Skills
· Experience in AWS or Azure Cloud and container technologies like Docker, Kubernetes, etc.
· DB solutions: MySQL, SQL Server, PostgreSQL, MongoDB
· Cache: Redis and Memcached
· CI/CD: Jenkins CI, Git, Gitlab CI, Helm for Kubernetes
· Tools: JIRA, Confluence, Git, Ansible, Terraform, Helm, Prometheus, Grafana
· On Call Support: Pagerduty

Minimum Qualifications
· Bachelor’s Degree in Computer Science, Computer Engineering or equivalent professional experience
· 4+ years of prior experience in DevOps, Site Reliability or Platform Engineering
· Highly proficient in one of programming languages such as Python, Go or Java
· Strong Scripting Skills in Bash or PowerShell
· Strong background in Public clouds like AWS or Azure along with infrastructure as a code(Terraform, CDK)
· Strong Experience with continuous integration and related tools such as Jenkins Pipelines, GitHub Actions, ArgoCD, Gitlab CI, SonarQube
· Experience in managing Kubernetes Clusters
· Experience with Scrum and Agile workflow methodologies

Other Relevant Qualifications
· Certified AWS Solutions Architect- Associate or higher
· Azure Fundamentals or higher
· Any Kubernetes Certifications (KCNA, KCSA, CKAD, CKA, CKS)
· HashiCorp Certified: Terraform Associate

Pay is determined by several compensable factors, such as qualifications, skill level, competencies, and work location.  
- $90,000.00 - 120,000.00 annually

Why Lessen:
·        Competitive compensation
·        Health, Dental, Vision, Life, Disability options
·        401K retirement savings plan
·        Paid vacation, federal and floating holidays
·        Maternity/Paternity Pay
·        Career advancement opportunities
·        All the tools you'll need to be successful

Lessen is intentional about attracting, developing, and retaining amazing talent from diverse backgrounds. We’re looking for teammates that are enthusiastic, empathetic, curious, motivated, reliable, and will help us amplify the positive & inclusive culture we’ve been building.  Lessen is an Equal Opportunity Employer.  All qualified applicants will receive consideration for employment without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, age, protected veteran or disabled status, or genetic information. 

Lessen LLC Chicago, Illinois, USA Office

Lessen LLC Chicago, IL Office

203 N. LaSalle St., Suite 2200, Chicago, IL, United States, 60601

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