Senior Software Engineer - AI & Audit Automation

Caribou Systems, Inc. is building next-generation AI-supported audit automation in a secure, closed-platform environment, with strong controls and human verification at every step. In this role, you will help harden and expand production systems that transform audit documents into structured, auditable outputs, while maintaining traceability from source to final result.

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 pre-loaded with curated content.
• Create human-in-the-loop review workflows so automated outputs are verified by an auditor before use, with full traceability back to the source document.
• Maintain and strengthen a secure closed platform including role-based access control, encryption in transit and at rest, audit logging, and least-privilege access for a need-to-know user base.
• Improve extraction and template output quality through accuracy measurement, regression testing, and quality benchmarks.
• 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 that connect 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 the 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, plus experience with data pipelines and document processing such as parsing, OCR, and structured extraction.
• Hands-on experience integrating LLM or NLP capabilities into production workflows, including prompt design, output validation, and evaluation.
• Security-minded engineering practices: 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 collaborating directly with non-engineering stakeholders such as auditors and compliance teams.

Technologies you’ll work with

• 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
• LLM, NLP, OCR

Preferred experience

• Experience in healthcare, employee benefits, claims administration, or audit/compliance domains.
• Familiarity with compliance and security frameworks (for example, 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.

Benefits

• 401(k) and 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, and paid time off
• Prescription drug insurance
• Vision insurance
• Work from home