Job · Chicago, IL · Full time

Principal AI Engineer

Cna Employees' Health Plan Trust · $85.6M budget · Since 1988

Why Cna Employees' Health Plan Trust

FY2024 · Form 990Its mission and biggest programs, as filed

Offers health, welfare, and unemployment benefits to VEBA members.

  • The primary purpose of this tax exempt irc section 501(c)(9) voluntary Employees' beneficiary association ("veba") is to provide permissible welfare benefits to the veba members. The veba Trust provided benefits for 5,328 active participants and 457 retired or separated participants…$90M spent in FY2024

Before you apply

FY2024 · Form 990Independent: from IRS data, not the org
Budget
$90.0M
spent in FY2024
Fine: from the org's Form 990.
Pt I · Ln 18
Spent on programs
100%
of spending
Looks good: 100% of spending went to programs; 75% or more.
Pt IX · Ln 25 · col B
Surplus or deficit
−5%
of revenue, FY2024
Concern: revenue was below expenses in the latest filing.
Pt I · Ln 19
Cash reserves
<1 mo
of spending, in cash and securities
Concern: 0.3 months of spending in cash; under 2 weeks.
Pt X · Ln 1–2 · Pt I · Ln 18
Latest return
FY2024
latest Form 990
Looks good: the latest return is for FY2024, 2 tax years back; within 2 tax years.
IRS e-file
IRS status
501(c)(9)
tax-exempt since 1988
Looks good: listed by the IRS.
IRS BMF
Looks goodFineWorth a lookConcernTap a box for the reason.

About the role

The org's own posting, as written

You have a clear vision of where your career can go. And we have the leadership to help you get there. At CNA, we strive to create a culture in which people know they matter and are part of something important, ensuring the abilities of all employees are used to their fullest potential. Individual contributor providing the highest level of technical leadership in the design, development, and scaling of CNA's AI-native agentic engineering platform.

This role operates at the intersection of AI systems engineering, developer experience, and software delivery — building the foundational platform capabilities that enable the broad engineering organization to build, ship, and run high-quality, secure AI-native systems at the speed of AI. The focus is on designing and delivering agentic workflows, AI-augmented CI/CD pipelines, reusable skills and agent frameworks, and quality/security guardrails that make AI-accelerated delivery safe and scalable across the enterprise.

JOB DESCRIPTION

Essential Duties & Responsibilities Performs a combination of duties in accordance with departmental guidelines: Acts as one of principal engineers for CNA's AI-native engineering platform, designing the end-to-end system spanning agentic coding workflows, skills and agent marketplaces, AI-augmented CI/CD pipelines, automated quality gates, and rapid environment provisioning. Leads integration of AI tooling (Claude Code, Cursor, GitHub Copilot) into the software delivery lifecycle, ensuring these capabilities compose into a coherent, governed platform.

Designs and builds the agentic infrastructure layer — including multi-agent orchestration patterns, sub-agent frameworks, skill authoring standards, and context engineering best practices — that enables engineering teams to operate at AI-native speed without sacrificing architectural integrity or security posture. Provides expert technical consultation to engineering leadership, portfolio teams, and architecture on how to adopt AI-native development practices, evaluate AI-generated code quality, and integrate agentic tooling into existing workflows.

Advises on trade-offs between speed and quality, human-in-the-loop requirements, and appropriate levels of AI autonomy for different risk profiles (e.g., Sox-classified systems vs. rapid prototyping). Leads the technical strategy and implementation for engineering metrics platform . Consult with senior tech leadership stakeholders to provide insights in data-driven decision making.

Acts as the senior technical resource mentoring engineers across the organization in AI-native engineering practices — including agentic coding patterns, context engineering, prompt-to-code workflows, and AI-assisted testing — raising the floor of capability so teams become self-sustaining without ongoing coaching dependency. Researches , evaluates, and recommends AI engineering tools, frameworks, and infrastructure (e.g., eval platforms, agent orchestration systems, environment provisioning…

Read the full posting

About Cna Employees' Health Plan Trust

From its Form 990

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