Principal AI Software Engineer

Taxwell helps everyday Americans get every tax advantage they deserve by finding credits and deductions they never even knew existed. Our tax preparation software offers easy guidance and ensures your maximum tax refund. We strive to build a team of like-minded experts in both tax and technology who align with our brand purpose, are advocates for our customers and have a fresh, non-traditional approach to the tax industry. Taxwell is a leading digital tax filing platform formed in 2022 from the combination of Drake Software® and TaxAct®. These two longstanding organizations offer customers professional and do-it-yourself digital and downloadable products that are easy-to-use, best-in-class technology, and provide unparalleled customer support. Taxwell brands are a trusted solution for all users including those with complex tax returns. We strive to attract and retain candidates who exemplify our values: performance, perseverance, progress and partnership. Taxwell is an organization of forward thinkers looking to add industry experts to our growing team. Description: We are seeking a Principal AI Engineer to lead the design, development, and deployment of AI-powered systems across Taxwell. These systems include: AI tools and applications used across multiple internal departments (engineering, operations, support, product, tax, compliance, and more) Customer-facing AI capabilities embedded in our existing products The creation of entirely new AI-native products that leverage AI as a foundational capability ​ This is a senior, hands-on technical role for an engineer who has operated at the Principal level and has a strong track record of turning emerging AI capabilities into production-grade systems with real business impact. You will act as both a technical leader and a multiplier—shaping architecture, setting standards, and enabling teams across the company to build effectively with AI. RESPONSIBILITIES: AI Platforms & Internal Enablement 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. Customer-Facing AI & AI-Native Products 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. Technical Leadership & Strategy 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. REQUIRED QUALIFICATIOS: 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. PREFERRED QUALIFICATIONS: 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). At Taxwell, we believe our work benefits from the diverse perspectives of our employees. As such, Taxwell welcomes and celebrates diversity and inclusion and is committed to equal opportunity employment. At Taxwell, you can expect a supportive, open, and inclusive atmosphere and a team that values your contributions. Taxwell is committed to providing an environment of mutual respect where equal employment opportunities are available to all applicants without regard to race, color, religion, sex, national origin, age, disability, marital status, sexual orientation, gender identity, veteran status, and any other status protected under applicable law. Taxwell considers information gathered in the hiring process, including information on this application, confidential, and only shares it on a need-to-know basis or as required by law. If you need assistance or accommodation due to a disability, you may contact us at [email protected] or by calling 828-349-5887 to speak with a member of the HR Talent Acquisition team.