Lead Software Engineer, AI Driven Reliability & Su

at Morningstar, Inc. in Chicago, Illinois, United States Job Description TheMission Financial advisorsrely heavily onMorningstar's Direct AdvisorySuiteand when software breaks, theyneed instant resolution.

OurDelight team transforms support from cost center into competitiveadvantageby combininghardcoreproductionengineeringwithAI-enhanceddiagnosisto deliver service excellence competitorscan'treplicate.

You'llwork on the hardest engineering problems (brownfield legacy systems at scale) while building AI tools thatdramatically accelerateproblemsolving.

You'llshape product strategy, not just fix bugs, proving that service excellencedrives revenue andsustainablecompetitive advantage. This position requires working from the Chicago office Monday through Thursday.

ThisRoleIsIdealIf You:

Excel duringproduction chaos and love being the "fixer" when systemsstart tofail ViewAI as a force multiplier for engineering work, not a replacement for deep technical knowledge Wantyour work to directly protecthundreds of millions in revenue Areenergized by brownfield complexity that greenfield developers avoid Understandsservice excellencecan be a durable competitive moat WhatYou'llDo 40-50%:

ProductionFirefighting&DeepTroubleshooting Debug urgent production issues across 20+ years of legacy systems (C#, .NET, Python, SQL)withlimited documentation and tightly coupled dependencies. Manually reproduce customer issues, isolate root causes, and deploy fixes under time pressurewhile partneringwith L1/L2 support teams to resolve high-priority advisor tickets. Maintainuptime for mission-critical financial systemsis nonnegotiable, requiring careful fixes that avoid downstream risk. 30-40%:

BuildtheDiagnosticFlywheel You will design and deploy AIagentsthat continuously improve detection, diagnosis, and resolution.

This includes:

Agentic andMCP poweredtools that mine historical RCA toidentifypatterns. Systems that simulate issues, recommend fixes, automate workflows, and reduce dependency on manual troubleshooting. Evolving support from reactive (human drivenfixes) to proactive (preventing issues before advisors notice). Your work will create compounding efficiency gains as the diagnostic flywheel learns and adapts. 10-20%:

StrategicEngineering⪻oductInfluence You will convert recurring support insights into product intelligence, shaping roadmap priorities based on advisor pain points.

You'llcontributePRs across thecodebase, reinforcing a culture of shared ownership.

You'llalso mentor teammates on AI adoption while upholdingproduction gradeengineering standards.

RequiredSkills:

ProductionEngineering(Critical) 7+ years debuggingenterpriseproduction systems under pressure Expert troubleshooting across full stack: backend (C#, .NET Core), databases (SQL/NoSQL), AWS infrastructure Strong SQL skills for data investigation and manual fixes RESTful APIs, microservices, and distributed systems debugging AI/AgenticWorkflows(GrowingImportance) Hands-on experience building LLM-powered tools (notcopy pasting fromChatGPT) Understanding ofContext engineering,prompt engineering, andotherAInuances Experience with agentic frameworks or MCP servers is a plus Python for automation and AI tooling

Cloud&DevOps AWSproficiency:

ECS, Lambda, RDS, DynamoDB, CloudWatch, S3 Infrastructure-as-code (Terraform, CloudFormation) CI/CD pipelines and modern deployment practices APM tools (DataDog, New Relic, etc.) How the work gets done Empathy for advisors and support teams

• you'resolvingreal humanpain, not abstract engineering problems

Communication:

explain technical issues to non-technical stakeholders

Collaboration:

work with L1/L2 support, product teams, and other engineering teams via shared ownership model Bias for action: ship fixes fast, learn fast, iterate Compensation and Benefits At Morningstar we believe people are at their best when they are at their healthiest. That's why we champion your wellness through a wide range of programs that support all stages of your personal and professional life. Here are some examples of the offerings we provide: Financial Health 100% 401k match up to 6% of salary Stock Ownership Potential Company provided life insurance

• 1x salary + commission Physical Health Comprehensive health benefits(medical/dental/vision)including potential premium discounts and company-provided HSA contributions (up to $500
• 2,000 annually) for specific plansand coverages Additional medical Wellness Incentives
• up to $300
• 600 annual Company-provided.

.. For full info follow application link. Morningstar and its subsidiaries are an equal opportunity/affirmative action employer. All qualified applicants will receive consideration for employment without regard to race, color, ancestry, religion, sex, national origin, age, disability, protected veteran status, marital status, sexual orientation, genetic information, citizenship, gender identity, parental status, or other legally protected characteristics or conduct. To view full details and how to apply, please login or create a Job Seeker account