Lead Software Engineer, AI Driven Reliability & Support

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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&ProductInfluence

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 long- and short-termdisabilityinsurance

  • Emotional Health

    • Trust-Based Time Off

    • 6-week Paid Sabbatical Program

    • 6-Week Paid Family Caregiving Leave

    • Competitive 8-24 Week Paid Parental Leave

    • Adoption Assistance

    • Leadership Coaching & FormalMentorshipOpportunities

    • Annual Flex Stipend – $1000 annually to cover personal education & well-being expenses

    • Tuition Reimbursement

  • Social Health

    • Charitable Matching Gifts program

    • Dollars for Doers volunteer program

    • Paid volunteering days

    • 15+ Employee Resource & Affinity Groups

Total Cash Compensation Range

$114,100.00 – 193,975.00 USD Annual

Inclusive of annual base salary and target incentive

Morningstar’s hybrid work environment gives you the opportunity to collaborate in-person each week as we’ve found that we’re at our best when we’re purposely together on a regular basis. In most of our locations, our hybrid work model is four days in-office each week. A range of other benefits are also available to enhance flexibility as needs change. No matter where you are, you’ll have tools and resources to engage meaningfully with your global colleagues.

001_MstarInc Morningstar Inc. Legal Entity
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.

 

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