Principal AI Data Scientist

About the Company

Taxwell is a leading digital tax filing platform formed in 2022 from the combination of Drake Software® and Tax Act®. 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.

About the Role

We are seeking a Principal AI Data Scientist 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 into existing products to deliver intelligent, AI-powered experiences
• Design and development of vertical AI solutions for the tax and compliance industry, as well as AI-native products built with generative AI at their core

This is a senior, hands-on technical role for a Data Scientist 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’ll apply technical expertise across AI evaluation, retrieval optimization, memory and state management, and AI agent architecture to support real-time insights and decision-making.

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 evaluation strategies covering model quality, retrieval optimization, benchmarking, and performance monitoring for deployed AI systems.
• 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 Dev Ops, 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 Lang Chain, Lang Graph, 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.

Qualifications

• 8+ years of Data Science experience, including 3+ years' operating at a Principal or Staff-level role.
• 5+ years of experience with…