Principal AI Software Engineer

TAXWELL•Haverford, PA

About The Position

Taxwell is seeking a Principal AI Engineer to lead the design, development, and deployment of AI-powered systems across the company. The work includes internal AI tools and applications for departments such as engineering, operations, support, product, tax, and compliance; AI capabilities embedded in existing customer products; and new AI-native products built around AI as a foundational capability. This is a senior, hands-on technical role for an engineer with Principal-level experience and a record of turning emerging AI capabilities into production-grade systems with measurable business impact. The role combines technical leadership and hands-on development, shaping architecture, setting standards, and enabling teams across Taxwell to build effectively with AI. The successful candidate will help ensure AI systems are scalable, observable, secure, compliant, reliable, explainable, and trusted, particularly in the regulated tax domain. Taxwell is a digital tax filing platform formed in 2022 through the combination of Drake Software and TaxAct. The company welcomes diverse perspectives and is committed to equal opportunity employment and an inclusive workplace.

Requirements

10 or more years of software engineering experience, including 3 or more 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, such as Pinecone, FAISS, or Chroma.
Experience deploying and operating systems on AWS, GCP, or Azure.
Strong architectural judgment and the ability to balance experimentation with production rigor.

Nice To Haves

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, such as GPT-OSS-120B, Mistral 3, or GLM-4.7.

Responsibilities

Design and build AI-powered tools that improve productivity across engineering and non-engineering teams, including developer workflows, customer support, tax development, operations, compliance, and analytics.
Develop internal AI platforms, shared services, and reusable components that help teams build AI-powered applications safely and effectively.
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 in existing Taxwell products to improve accuracy, usability, personalization, and customer outcomes.
Architect and build new customer-facing products in which AI is a core differentiator.
Work with product, design, and tax domain experts to turn user problems into effective AI-powered solutions.
Ensure AI features meet high standards for reliability, explainability, and trust, especially in the regulated tax domain.
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 reviews and hands-on collaboration.
Measure system effectiveness using telemetry, automated metrics, and qualitative feedback from internal and external users.