Applied AI Engineer

OLarry is a tax and technology company focused on making tax preparation and planning more accessible and efficient. The Applied AI Engineer will define, plan, and implement AI-driven tax solutions, including document extraction, scenario planning, forecasting, recommendations, and user-facing tools. The role also involves owning machine learning pipelines and delivering reliable AI features for customers, financial advisors, and CPAs.

Responsibilities:

• Ensure the timely and high-quality delivery of engineering projects by setting clear priorities and deadlines
• Build a pipeline that takes messy PDFs or scanned tax docs and extracts structured, searchable data — even when the AI gets it half-right
• Fine-tune how we use AI and vector search to automatically classify uploaded documents into categories like “Filed Return” or “Supporting Doc”
• Create a confidence scoring system for LLM outputs so downstream services know when to trust the data, and when to loop in a human
• Prototype an AI-driven “Tax Scenario Planner” where users can explore what happens to their taxes if they sell stock, start a side business, or move states
• Build a module that looks at a customer’s past return data and suggests tax-saving opportunities or gaps, using both rules and AI inference
• Implement a forecasting tool that simulates future tax outcomes based on different income streams and entity structures
• Help design a system that asks smart follow-up questions to refine a scenario, like an AI-powered tax assistant
• Build LLM-powered summarization tools that explain complex return data to non-experts in plain language
• Create internal tools for financial advisors or CPAs to visualize multiple return scenarios side-by-side for their clients
• Explore collaborative filtering approaches to recommend planning strategies based on what similar users have done, without breaching data privacy