Senior Software Engineer - AI & Audit Automation

Caribou Systems, Inc. is building next-generation AI-supported audit automation in a secure, closed-platform environment. This role owns production-grade workflows end to end, from document intake to verified outputs and audit-ready traceability, with a strong focus on measurable AI behavior, controlled integrations, and human-in-the-loop review by auditors.

What you’ll build

• 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 that are pre-loaded with curated content.
• Create human-in-the-loop review workflows so every automated result is verified by an auditor before use, with full traceability from output back to source documents.
• Harden and evolve the secure, closed platform including role-based access control, encryption in transit and at rest, audit logging, and least-privilege access for need-to-know users.
• Improve accuracy measurement through regression testing, quality benchmarks, and evaluation tooling for extraction and template outputs.
• Extend automation across additional stages of the audit lifecycle, from intake through findings documentation.
• Design evaluation and monitoring tooling to keep model behavior measurable, explainable, and controlled as capabilities expand.
• Build integrations and internal APIs connecting the platform to adjacent audit tooling while preserving the closed-platform security model.
• Contribute to architecture decisions, technical standards, and documentation to support scaling beyond a current pilot scope.

What you bring

• 5+ years of professional software engineering experience, including end-to-end ownership of production systems.
• 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/NLP capabilities into production workflows, including prompt design, output validation, and evaluation.
• Security-minded engineering habits: access control, secrets management, encryption, and experience working within closed or restricted environments.
• Pragmatic judgment on where AI adds value versus where deterministic logic and human review are the right approach.
• Clear written communication and comfort working directly with auditors and compliance stakeholders.

Technology focus

C#, .NET, Java, Microsoft Azure, Azure AI services, Azure OpenAI, SQL Server, Azure SQL, T-SQL, Git-based source control, CI/CD pipelines (Azure DevOps, GitHub Actions), plus LLM, NLP, OCR.

Preferred background

• Experience in healthcare, employee benefits, claims administration, or audit/compliance domains.
• Familiarity with compliance and security frameworks (for example SOC 2, HIPAA) and handling 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 inheriting it.

Benefits

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