Principal AI Software Engineer

Taxwell is a leading digital tax filing platform formed from the combination of Drake Software and TaxAct. They are seeking a Principal AI Engineer to lead the design, development, and deployment of AI-powered systems across the organization, enhancing both internal operations and customer-facing products.

Responsibilities:

• Design and build AI-powered tools that improve productivity across engineering and non-engineering teams (e.g., developer workflows, customer support tooling, tax development, operations, compliance, and analytics)
• Develop internal AI platforms, shared services, and reusable components that enable teams to safely and effectively build AI-powered applications
• Build and maintain retrieval-augmented generation (RAG) systems grounded in internal documentation, codebases, tax knowledge, and proprietary data
• Partner with DevOps, platform, and security teams to ensure AI systems are scalable, observable, secure, and compliant
• Embed AI capabilities into existing Taxwell products to improve accuracy, usability, personalization, and customer outcomes
• Architect and build new customer-facing products where AI is a core differentiator, not an add-on
• Work closely with product, design, and tax domain experts to translate real user problems into effective AI powered solutions
• Ensure AI features meet high standards for reliability, explainability, and trust—especially in a regulated domain like tax
• Design and implement agent-based systems using frameworks such as LangChain, LangGraph, ADK, or similar
• Evaluate and integrate commercial and open-source AI technologies, including frontier models and open-weight LLMs
• Establish best practices for prompt engineering, evaluation, monitoring, and continuous improvement of AI systems
• Influence AI architecture and technical direction across the organization through design review and hands-on collaboration
• Measure system effectiveness using telemetry, automated metrics, and qualitative feedback from internal and external users

Requirements:

• 10+ years of software engineering experience, including 3+ years' operating at a Principal- or Staff-level role
• Proven experience designing and deploying production AI systems used by real users
• Strong hands-on experience with LLM-enabled systems, including prompt engineering, RAG, and agent orchestration
• Proficiency in Python and/or TypeScript
• Experience integrating AI systems with real-world applications, workflows, and data sources
• Familiarity with vector databases and embedding techniques (e.g., Pinecone, FAISS, Chroma)
• Experience deploying and operating systems on AWS, GCP, or Azure
• Strong architectural judgment and the ability to balance experimentation with production rigor
• Experience building AI platforms or internal copilots used across multiple teams or departments
• Experience developing customer-facing AI products at scale
• Background in regulated industries such as fintech, tax, or healthcare
• Experience fine-tuning or customizing open-weight models (e.g.,GPT-OSS-120B, Mistral 3, GLM-4.7)