Senior Software Engineer - AI & Audit Automation

Caribou Systems, Inc. is building AI-supported automation that makes complex audit work faster, more consistent, and more reliable. Our platform ingests healthcare contracts and plan documents and helps generate the auditor templates our teams use to verify that claims are administered according to plan terms. We are looking for a Senior Software Engineer to take a leading role in hardening the current platform and building out its next generation. This is a hands-on role with broad ownership: you will work across document ingestion, AI-assisted extraction and template generation, and the secure infrastructure the platform runs on.

What you’ll work on

Current platform:

• Design, build, and maintain ingestion pipelines that convert contracts and plan documents (PDF, Word, scanned images) into clean, structured, auditable data.
• Develop and refine AI-assisted extraction and auditor template generation, using controlled, non-learning model configurations pre-loaded with curated content.
• Build human-in-the-loop review workflows so every automated output is verified by an auditor before use, with full traceability from output back to source document.
• Maintain and strengthen the secure, closed platform environment: role-based access control, encryption in transit and at rest, audit logging, and least-privilege access for a need-to-know user base.
• Improve accuracy measurement, regression testing, and quality benchmarks for extraction and template outputs.

Future architecture:

• Extend automation across additional stages of the audit lifecycle, from intake through findings documentation.
• Design evaluation and monitoring tooling that keeps model behavior measurable, explainable, and controlled as capabilities expand.
• Build integrations and internal APIs that connect the platform to adjacent audit tooling while preserving the closed-platform security model.
• Contribute to architecture decisions, technical standards, and documentation that allow the platform to scale beyond its current pilot scope.

• 5+ years of professional software engineering experience, including ownership of production systems end to end.
• Strong backend engineering skills in .NET (C#) and/or Java, with experience in data pipelines and document processing (parsing, OCR, structured extraction).
• Hands-on experience integrating LLM or NLP capabilities into production workflows, including prompt design, output validation, and evaluation.
• Security-minded engineering habits: access control, secrets management, encryption, and working within closed or restricted environments.
• Pragmatic judgment about where AI adds value and where deterministic logic and human review are the right tool.
• Clear written communication and comfort working directly with non-engineering stakeholders such as auditors and compliance teams.

Technical environment:

• Languages and frameworks: C#/.NET and Java; comfort working across both is a plus.
• Cloud: Microsoft Azure, including compute, storage, identity/access management, and Azure AI services.
• Data: SQL Server / Azure SQL, T-SQL, and sound relational data modeling for document-derived data.
• AI integration: LLM services (e.g., Azure OpenAI) with controlled configurations, output validation, and evaluation.
• Tooling: Git-based source control and CI/CD pipelines (e.g., Azure DevOps or GitHub Actions).

Preferred experience:

• Experience in healthcare, employee benefits, claims administration, or audit/compliance domains.
• Familiarity with compliance and security frameworks (e.g., SOC 2, HIPAA) and handling of sensitive client documents.
• Experience building internal tools with human-in-the-loop review UX.
• Prior work in small teams or early-stage products where you shaped architecture rather than inherited it.

Pulled from the full job description Prescription drug insurance AD&D insurance 401(k) Health insurance 401(k) matching Paid time off Vision insurance, * 401(k)

• 401(k) matching
• AD&D insurance
• Dental insurance
• Dependent health insurance coverage
• Disability insurance
• Employee assistance program
• Flexible spending account
• Health insurance
• Life insurance
• Paid holidays
• Paid sick time
• Paid time off
• Prescription drug insurance
• Vision insurance
• Work from home