AI Engineer, Tax Document Intelligence & Workflows

Stealth Startup YC backed; Chicago (IL); On-site; USD 150,000 - 200,000; Full time

Job summary

Stealth Startup YC backed in Chicago seeks an AI engineer to own the intelligence layer across the document-to-return workflow. You will design production AI systems that convert messy documents into machine-readable tax data and support tax professionals with confidence signals and source citations.

Join a small, high-ownership team building the core tax engine and interfaces, collaborating with tax professionals and engineers to improve accuracy, speed, and auditability in real-world filings.

Qualifications

• Experience building robust OCR and extraction for PDFs, forms, and scanned docs.
• Design scalable evaluation frameworks with ground-truth labels and metrics.
• Strong judgment on observability, reproducibility, and AI-in-the-loop workflows.
• Bias toward shipping real-world document AI with auditability and reliability.

Responsibilities

• Build systems that classify client documents and extract reliable tax data.
• Design end-to-end workflows to extract fields and resolve ambiguity.
• Develop agents to compare a completed return with source documents and suggest corrections.
• Define confidence signals, citations, and review workflows.
• Establish observability and feedback to measure QA and outcomes.

Skills

Document OCR

LLM‑based Document Understanding

Structured Data Extraction

Evaluation Framework Design

Ground-Truth Labeling

Statistical Analysis

Agentic Systems

Human-in-the-Loop Workflows

Observability

Reproducibility

Production AI Systems

Python

Job description

Stealth Startup YC backed in Chicago seeks an AI engineer to own the intelligence layer across the document-to-return workflow. You will design production AI systems that convert messy documents into machine-readable tax data and support tax professionals with confidence signals and source citations.

Join a small, high-ownership team building the core tax engine and interfaces, collaborating with tax professionals and engineers to improve accuracy, speed, and auditability in real-world filings.