Remote Observability Engineer Jobs in Chicago, IL

At Allstate, great things happen when our people work together to protect families and their belongings from life’s uncertainties. And for more than 90 years, our innovative drive has kept us a step ahead of our customers’ evolving needs. From advocating for seat belts, air bags and graduated driving laws, to being an industry leader in pricing sophistication, telematics, and, more recently, device and identity protection. 

Job Description

Allstate is seeking an experienced Lead Product Engineer to join its enterprise application monitoring product within the observability group. This role focuses on configuring, implementing, and supporting end-to-end monitoring for applications and platforms across on-prem, private, and public cloud environments. The engineer leads the design, architecture, and engineering of digital products, applying advanced software development principles to ensure successful delivery, testing, maintenance, and documentation. They manage production applications, meet KPIs, and foster a culture of prompt issue identification and availability. The role promotes reliability by collaborating with security, platform engineering, and services teams, while aligning software engineering efforts with the organization's vision for Enterprise Monitoring and Observability.
The Lead Product Engineer supports the product lifecycle from inception through implementation and daily operations. They interpret technical requirements to design optimal monitoring and IT system solutions, leveraging knowledge of business processes, systems architecture, and modern monitoring technologies. Additionally, the engineer plans, directs, and executes complex IT-related activities and programs, ensuring robust and scalable observability systems across the enterprise.

Key Responsibilities

• Understand Allstate’s core business drivers, articulate business objectives, align with strategic direction, prepare long-range plans, prioritize objectives, and practice policies.

• Apply advanced engineering excellence practices by enforcing technical standards, promoting test-driven development (TDD), and recommending scalable, system-aligned solutions that support both business growth and technology strategy.

• Promote system thinking by influencing stakeholders to prioritize enterprise-wide benefits and risk mitigation. Champion the adoption of standardized patterns, reusable components, and architectural roadmaps.

• Shape platform strategy by collaborating with platform consultants to design forward-looking standards and patterns that reflect emerging technology trends and evolving business models.

• Facilitate alignment across strategic domains by engaging with the appropriate Areas of Responsibility, business architects, and senior leaders to deliver integrated, high-impact solutions. Act as a connector between application and infrastructure domains to ensure cohesive system design.

• Apply reference architecture and enterprise technology strategy to guide solution design. Serve as a subject matter expert with contextual understanding of business operations and technology ecosystems.

• Engineer for resilience and performance by partnering with architecture and engineering teams to define infrastructure solutions that meet stringent performance, availability, capacity, and resiliency goals.

• Develop and maintain infrastructure roadmaps that align business direction with technology evolution. Regularly review these roadmaps with product management to ensure strategic alignment.

• Design, develop, analyze, and report on critical metrics to provide insights into overall health and ensure effective communication.

• Coach and consult on environment sizing, deployment strategies, disaster recovery planning, and architectural best practices for application portfolios and support teams.

• Lead inception and D&F of complex application solutions. Ensure thorough documentation and clear communication of designs to stakeholders.

• Serves as an expert on multiple business domain and a distinguished advocate of multiple technology stacks and shares that knowledge across organizations

Essential Skills

• 5+ years of overall engineering experience, including designing or building software, tools, or automation that enable observability for distributed platforms and infrastructure. (Preferred)

• 4 years of hands-on experience supporting at least one major observability platform (Datadog, Dynatrace, New Relic, AppDynamics, or OTEL), including configuration, dashboards, alerting, and integrations. (Preferred)

• 3 years working in Agile environments with applied understanding of Site Reliability Engineering (SRE) principles such as SLIs/SLOs, error budgets, and operational readiness.

• 3 years of development experience using one or more programming languages (Spring Boot/Java, Python, ReactJS, NodeJS), contributing to monitoring tools, automation, or integrations.

• Proven hands-on experience with Kubernetes, plus practical experience on both Windows and Linux systems in enterprise or cloud environments.

• Demonstrated interest and emerging experience applying new technologies, including Agentic AI–based solutions that improve observability, automation, or operational efficiency.

• Strong written and verbal communication skills of engineering or technical delivery work, including documentation and presentations to technical and executive stakeholders.

 

Supervisory Responsibilities

• This job does not have supervisory duties.

(#LI-NJ1)

Skills

Agile Methodology, Agile Methodology, AppDynamics, Application Monitoring, Building Architecture, Business, Business Direction, Business Objectives, Business Operations, Business Processes, Business Software, C (Programming Language), Cloud Infrastructure, Collaborating, Collaborative Development, Computer Science, Compuware dynaTrace, Core Business, Datadog, Design, Disaster Recovery (DR), Disaster Recovery Planning, Emerging Technologies, Emerging Technology Trends, End-to-End Testing {+ 38 more}

Compensation

Compensation offered for this role is 100,000.00 - 170,500.00 annually and is based on experience and qualifications.

The candidate(s) offered this position will be required to submit to a background investigation.

Joining our team isn’t just a job — it’s an opportunity. One that takes your skills and pushes them to the next level. One that encourages you to challenge the status quo. One where you can shape the future of protection while supporting causes that mean the most to you. Joining our team means being part of something bigger – a winning team making a meaningful impact.

Allstate generally does not sponsor individuals for employment-based visas for this position.

Effective July 1, 2014, under Indiana House Enrolled Act (HEA) 1242, it is against public policy of the State of Indiana and a discriminatory practice for an employer to discriminate against a prospective employee on the basis of status as a veteran by refusing to employ an applicant on the basis that they are a veteran of the armed forces of the United States, a member of the Indiana National Guard or a member of a reserve component.

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It is the Company’s policy to employ the best qualified individuals available for all jobs. Therefore, any discriminatory action taken on account of an employee’s ancestry, age, color, disability, genetic information, gender, gender identity, gender expression, sexual and reproductive health decision, marital status, medical condition, military or veteran status, national origin, race (include traits historically associated with race, including, but not limited to, hair texture and protective hairstyles), religion (including religious dress), sex, or sexual orientation that adversely affects an employee's terms or conditions of employment is prohibited. This policy applies to all aspects of the employment relationship, including, but not limited to, hiring, training, salary administration, promotion, job assignment, benefits, discipline, and separation of employment.