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Lead Product Engineer Agentic AI Observability - Remote

Remote / Online - Candidates ideally in
Chicago, Cook County, Illinois, 60290, USA
Listing for: Allstate Insurance Company
Remote/Work from Home position
Listed on 2026-07-20
Job specializations:
  • Software Development
    AI Engineer (Applied/Software), DevOps, Software Architect, Cloud Engineer - Software
Salary/Wage Range or Industry Benchmark: 100000 - 170500 USD Yearly USD 100000.00 170500.00 YEAR
Job Description & How to Apply Below
Position: Lead Product Engineer – (Agentic AI for Observability) - Remote

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 a forward‑thinking Lead Product Engineer to drive innovation in its AI‑powered Observability platform. This role sits at the intersection of AI engineering, observability, and software development, with a strong focus on automation, intelligent insights, and self‑healing systems across hybrid and multi‑cloud environments.

You will lead the design and development of next‑generation observability solutions powered by agentic AI, enabling proactive detection, diagnosis, and remediation of issues.

This role emphasizes building scalable platforms, intelligent automation, and developer‑centric tooling that enhance reliability, performance, and operational efficiency.

As a technical leader, you will shape product strategy, drive engineering excellence, and deliver AI‑driven monitoring and automation capabilities that transform how applications and platforms are operated across the enterprise.

Key Responsibilities
  • Design and build agentic AI solutions for observability, including autonomous agents capable of anomaly detection, root cause analysis, and automated remediation.
  • Embed AI/ML capabilities into observability platforms to enable predictive insights, anomaly detection, and intelligent alerting
    .
  • Develop AIOps frameworks that reduce noise, automate workflows, and improve incident response times.
  • Leverage LLMs and AI orchestration frameworks to create self‑service diagnostics and operational assistants
    .
  • Architect and implement end‑to‑end observability solutions across logs, metrics, traces, and events.
  • Enhance observability platforms (Datadog, Dynatrace, New Relic, App Dynamics, OTEL) with custom integrations, automation, and AI enhancements
    .
  • Build real‑time insights and health analytics to ensure system reliability, scalability, and performance.
  • Lead development of scalable, reusable platform components and APIs for observability and automation.
  • Build developer‑first tools and frameworks that simplify instrumentation, monitoring, and diagnostics.
  • Apply modern software engineering practices including TDD, CI/CD, microservices, and cloud‑native design
    .
  • Develop full‑stack solutions (backend services, dashboards, automation tooling) using Java/Spring Boot, Python, Node.js, and React
    .
  • Drive automation‑first strategies to eliminate manual operations and improve efficiency.
  • Build self‑healing systems that automatically detect and remediate issues.
  • Lead initiatives in infrastructure‑as‑code, Observability‑as‑code and automated deployment pipelines
    .
  • Engineer highly resilient systems by focusing on performance, scalability, and fault tolerance
    .
  • Define and evolve enterprise observability architecture
    , incorporating AI and automation as core principles.
  • Collaborate with architecture, platform, and security teams to align solutions with enterprise standards.
  • Champion standardization, reusable patterns, and platform scalability across the organization.
  • Act as a technical leader and mentor
    , guiding teams in AI, observability, and engineering best practices.
  • Partner with cross‑functional teams to deliver integrated, high‑impact platform solutions
    .
  • Communicate technical concepts and strategies effectively to both technical and executive audiences.
  • Foster a culture of innovation, automation, and continuous improvement
    .
Essential Skills
  • 5+ years of engineering experience building software, platforms, or automation solutions
    , with a strong emphasis on observability and distributed systems.
  • 4+ years of hands‑on experience with observability platforms (Datadog, Dynatrace, OTEL).
  • 3+ years of software development experience using Java (Spring Boot), Python, Node.js, or React.
  • 2+ years of hands‑on experience building agentic AI systems (autonomous agents, AI workflows, or AI‑native…
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