Senior AI Software Engineer

CNA • Chicago, IL

4d • Hybrid

About The Position

Senior individual contributor on the Developer Experience (DevX) platform team, responsible for designing, building, and operating an AI-native software delivery platform across five capability domains: FeedBack (AI intelligence, observability, DORA metrics), Enterprise Enablement (Internal Developer Portal, golden-path onboarding), Build & Delivery (CI/CD/CT, GitHub Actions, ArgoCD, Harness), Safety / Application Security (Veracode, SonarCloud, JFrog Xray, supply-chain security), and App Accelerator (container base images, dev containers, starter app templates). Leads the development of AI agentic SDLC workflows — autonomous and human-in-the-loop agents that accelerate code generation, PR review, test authoring, vulnerability remediation, and deployment across engineering teams — in direct support of the platform's north-star goal of taking a developer from template selection to a running pre-production application in 10 minutes or less. Acts as a force multiplier for DevX, partnering with platform, security, container, and product engineering to embed AI assistance into every stage of the SDLC.

Requirements

• 7+ years in platform engineering with deep CI/CD pipeline ownership in a regulated, enterprise-scale environment (insurance, financial services, or equivalent).
• Hands-on with GitHub Actions, ArgoCD , Harness, or comparable CD platforms — able to design and operate end-to-end, not just configure.
• Proficient using AI coding tools (Claude Code, Cursor, GitHub Copilot, or equivalent) in an AI-native SDLC workflow; experience building guardrails and adoption patterns for these tools at team or enterprise scale.
• Direct experience building or operating an Internal Developer Platform (Harness IDP, Backstage, Port) with a self-service catalog, golden-path scaffolding, and measurable time-to-value metrics (e.g., time to first deployment).
• Feature flags and progressive-delivery experience ( LaunchDarkly , Unleash, GCP-native, or equivalent) including kill-switch design and canary rollout patterns.
• SBOM and supply-chain integration experience ( JFrog Xray, Syft , Anchore ) inside a delivery pipeline, including Binary Authorization or equivalent container image hardening and policy-gate design.
• Hands-on with observability platforms (Datadog, Dynatrace, Elastic, or equivalent); able to instrument DORA metrics, define SLOs, and build actionable engineering-performance dashboards.
• Familiarity with SAST/DAST tooling (Veracode, SonarCloud , or equivalent) in an enterprise pipeline context — ideally including automated triage or remediation workflows.
• Experience designing and building event-driven AI agents that autonomously complete SDLC tasks, and building evals for agentic systems using Arize , Phoenix, or equivalent.
• Strong analytical and problem-solving skills; excellent communication and interpersonal skills; able to work effectively with engineers, IT leadership, security, and business stakeholders.
• Demonstrated ability to lead platform initiatives, drive cross-team adoption, and mentor engineers.
• Bachelor's degree in Computer Science or related discipline, or equivalent work experience.
• Minimum of 7 years of platform and software engineering experience, including direct ownership of enterprise CI/CD pipelines in a regulated industry.
• Previous technical leadership experience on platform, developer-tooling, or AI-engineering initiatives.

Nice To Haves

• Insurance or financial-services industry background; familiarity with regulatory and compliance requirements for software delivery.
• Experience with security-as-code, OPA/Rego policy authoring, or compliance-automation pipelines (e.g., GitHub governance at scale, branch protection policy-as-code).
• Hands-on with container base image pipelines, dev container standards, or starter app template frameworks.
• Open-source contributions to platform engineering, developer tooling, or AI-agent projects.
• Applicable certifications preferred (e.g., GitHub Actions, Kubernetes, cloud provider, or Harness certifications).

Responsibilities

• Own and evolve the Internal Developer Platform (Harness IDP) — self-service catalog, scaffolding templates, and golden-path workflows targeting the platform's north-star goal: developer selects a template and has an application deployed to pre-production in 10 minutes or less.
• Architect and own CI/CD/CT pipelines on GitHub Actions, ArgoCD , and Harness across the Build & Delivery domain ; design for reliability, security, and progressive delivery — able to design and operate end-to-end, not just configure.
• Design and build AI agentic SDLC workflows: event-driven agents that autonomously perform code generation, PR review, test authoring, Veracode vulnerability auto-remediation, SonarCloud gate enforcement, and release orchestration across the delivery pipeline.
• Implement evaluation frameworks for agentic systems ( Arize , Phoenix, or equivalent) — define ground truth datasets, regression suites, guardrails, and online/offline evals to ensure AI agents operating inside the SDLC remain safe, accurate , and auditable.
• Drive supply-chain security inside the Application Security domain: integrate SBOM generation ( JFrog Xray, Syft , or Anchore ) into delivery pipelines, contribute to the Binary Authorization and container image hardening initiative for Kubernetes workloads, and design automated policy gates and remediation flows.
• Contribute to the App Accelerator domain — maintain and evolve container base images, dev container definitions, and starter app templates so that golden-path scaffolded applications are current, secure, and ready for AI-assisted development from day one.
• Operate feature flag and progressive-delivery platforms ( LaunchDarkly , Unleash, GCP-native, or equivalent); design kill-switches, canary patterns, and safe rollout strategies that protect production while enabling continuous delivery.
• Embed observability (Datadog, Dynatrace, Elastic, or equivalent) into platform services and delivery pipelines across the FeedBack domain; own DORA metric instrumentation (deployment frequency, lead time, change failure rate, MTTR) and Application Health dashboards used to measure engineering performance.
• Champion adoption of AI coding assistants (Claude Code, Cursor, GitHub Copilot) in an AI-native SDLC; build the guardrails, prompt patterns, and developer workflows that make AI-assisted development repeatable and safe at enterprise scale; contribute to the Code Quality as a Service offering alongside Veracode and SonarCloud .
• Mentor engineers across the DevX and App Accelerator teams; act as a technical consultant for platform adoption, agentic AI patterns, and delivery best practices.
• Partner with security, infrastructure, architecture, and product engineering counterparts on platform direction, roadmap, and architectural standards; represent DevX in cross-team initiatives spanning container governance, GitHub security controls, and CI/CD policy.
• May perform additional duties as assigned.

Benefits

• CNA offers a comprehensive and competitive benefits package to help our employees – and their family members – achieve their physical, financial, emotional and social wellbeing goals. For a detailed look at CNA’s benefits, please visit cnabenefits.com.

What This Job Offers

• Job Type: Full-time
• Career Level: Senior