Drake Software · 11 hours ago
Principal AI Software Engineer
United States
Full-time
Remote
Lead/Staff
10+ years expTaxwell 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.
AccountingSoftware
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
Qualification
Required
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
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)
Company
Drake Software
Drake Software is a complete professional tax preparation program for federal and state returns, business and individual. It is a sub-organization of Cinven.
501-1000 employees
Funding
Current Stage
Late StageLeadership Team
Jennifer Dills, CPA
Chief Financial Officer
Willa Kalaidjian
Chief Legal Officer and General Counsel
Recent News
2025-09-17
2025-03-31
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