{"id":1299733,"url":"https://alion.io/job/weekday-ai-engineer-5","title":"AI Engineer","company":{"id":7097,"name":"Weekday","domain":"weekday.works","url":"https://alion.io/company/weekday","size_band":"51-200","is_staffing_agency":true,"employer_type":"agency","is_intermediary":false,"listed_via":null,"ats_vendor":"Workable","truth_index":{"grade":"B","score":81,"open_postings":86,"ghost_share":0,"stale_share":0.977,"repost_share":0,"time_to_fill_p50_days":5,"computed_at":"2026-09-26T05:45:00Z"}},"role":"AI/ML","role_family":"AI/ML","seniority":null,"employment_type":"full_time","work_mode":"on_site","remote_scope":null,"remote_scope_basis":null,"remote_working_hours":null,"hiring_geo_confidence":"explicit","locations":["Chicago, United States"],"countries":["US"],"hiring_countries":[],"hiring_countries_total":0,"salary":null,"salary_estimate":{"min_usd":147000,"max_usd":317000,"period":"year","method":"role_country_seniority_unknown","sample_n":2391},"experience_years_min":null,"visa_sponsorship":false,"relocation_package":false,"has_equity":false,"technologies":[{"name":"AI Agents","optional":false},{"name":"Human-in-the-Loop","optional":false},{"name":"LLM","optional":false},{"name":"Machine Learning","optional":false},{"name":"OCR","optional":false},{"name":"Python","optional":false}],"status":"live","first_seen_at":"2026-09-26T11:01:47Z","employer_posted_date":"2026-09-26","last_verified_at":"2026-09-27T04:11:48Z","board_verified":true,"closed_at":null,"days_open":0,"trust":{"level":"ok","repost_count":null,"flags":[],"days_open":0},"description":"'\n: - ( - )\nExperience: 3+ yrs\nLocation: Chicago, Illinois, United States\nJob Type: Full-time\nWe are looking for an experienced AI Engineer to design and build the intelligence layer across a document-to-return workflow. The role focuses on developing production-grade AI systems that transform complex financial and tax documents into reliable, structured data and support tax professionals in identifying missing information, inconsistencies, and potential errors.\nThis is a hands-on engineering role focused on document intelligence, LLMs, extraction, agentic systems, evaluation, and human-in-the-loop workflows. The ideal candidate combines strong technical skills with a high bar for accuracy, traceability, observability, and production reliability.\nRequirements\nKey Responsibilities\nBuild production systems for document classification, OCR, parsing, and structured data extraction.\nProcess PDFs, scanned documents, tax forms, financial statements, receipts, and other unstructured financial information.\nDesign extraction workflows that preserve source context, handle ambiguity, and route low-confidence results for human review.\nDevelop LLM-powered document understanding and intelligent extraction capabilities.\nBuild AI agents that analyze completed returns against source documents and relevant tax context.\nIdentify missing information, inconsistencies, potential errors, and other issues and present findings clearly for professional review.\nDesign human-in-the-loop workflows that provide appropriate confidence signals, source citations, review controls, and correction mechanisms.\nBuild scalable evaluation frameworks for structured and unstructured document-processing systems.\nDefine evaluation datasets, ground-truth labels, scoring methodologies, benchmarks, and statistical analysis approaches.\nEstablish observability and feedback systems to measure extraction quality, model performance, and user outcomes.\nMonitor production AI workflows and continuously improve accuracy, reliability, and coverage.\nIdentify high-effort manual steps within document and return-preparation workflows where AI can provide measurable value.\nCollaborate with engineering and domain experts to translate real-world workflow requirements into reliable AI systems.\nEstablish reproducible testing and evaluation processes for models, agents, and extraction pipelines.\nContribute to expanding AI capabilities across document processing, return review, and professional workflows.\nWhat Makes You a Great Fit\n3+ years of experience building production AI, machine learning, or intelligent automation systems.\nStrong hands-on experience with document OCR, document understanding, parsing, and structured data extraction.\nExperience working with PDFs, forms, scanned documents, financial documents, or other complex unstructured data.\nStrong understanding of LLM-based document processing and modern AI techniques for extraction and reasoning.\nExperience designing and implementing evaluation frameworks for AI or machine-learning systems.\nStrong knowledge of evaluation datasets, ground-truth labeling, scoring methodologies, benchmarking, and statistical analysis.\nExperience building or working with agentic AI systems and human-in-the-loop workflows.\nStrong understanding of observability, reproducibility, model monitoring, and production AI reliability.\nProficiency in Python and experience building scalable production systems.\nStrong analytical and problem-solving skills with exceptional attention to accuracy and detail.\nAbility to design AI workflows where outputs are traceable, auditable, explainable, and actionable.\nStrong product and engineering judgment with a practical, outcome-oriented approach to AI development.\nComfortable working closely with domain experts and incorporating real-world feedback into AI systems.\nStrong bias toward shipping, experimentation, measurement, and continuous improvement.\nComfortable operating in a small, high-ownership environment where engineering and product responsibilities are closely connected.","description_format":"text","description_chars":4052,"description_truncated":false,"requirements":{"experience_years_min":null,"management_years_min":null,"team_size_min":null,"manages_managers":false,"education":null,"security_clearance":false,"languages":[]},"benefits":[],"hiring_locations":[{"name":"United States","iso":"US","kind":"country"}],"hiring_excludes":[],"relocation_offered":false,"industries":[],"lifecycle":[{"event":"open","at":"2026-09-26T11:01:47Z"}],"liveness":{"score":52,"band":"ok","label":"Likely open","p_open":1,"p_active":0.516,"p_room":1,"age_days":0,"expected_fill_days":5,"reasons":["conf:0","agency","win:early","comp:brand"],"computed_at":"2026-09-27T05:06:30Z"},"pay":null,"html_url":"https://alion.io/job/weekday-ai-engineer-5","json_url":"https://alion.io/job/weekday-ai-engineer-5.json","meta":{"generated_at":"2026-09-27T05:06:30Z","cache_seconds":300,"methodology":"https://alion.io/methodology","terms":"https://alion.io/terms","contact":"https://alion.io/contact","api":"https://alion.io/developers","usage":{"tier":"crawler","counted_by":"address","units_charged":1,"used_today":4462,"day_limit":5000,"remaining_today":538,"minute_limit":60,"resets_at":"2026-09-28T00:00:00Z"}}}