Principal Software Engineer, AI-Augmented Development

Keystone AI 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. Drake Software is a leading digital tax filing platform whichoffers customers professional digital and downloadable products that are easy-to-use, best-in-class technology, and provide unparalleled customer support. We are a trusted solution for all users including those with complex tax returns. Westrive to attract andretaincandidates who exemplify our values: performance, perseverance,progressand partnership. Drake Software is a member of the Keystone AI family of products. We are an organization of forward thinkers looking to add industry experts to our growing team. This role will primarily support Drake Software as we provide the tools and support tax professionals need to build their businesses and attract new clients. We are an organization of problem solvers continually looking for solutions to support our customers. Our customers know they can rely on Drake Software for comprehensive product excellence and value. We’re looking for a Principal Software Engineer to drive critical initiatives across Drake Tax Online. This platform is central to how tax professionals prepare, review, and file returns—and requires thoughtful engineering across customer experience, platform architecture, scalability, reliability, and performance. This is a high-leverage, individual contributor (IC) role. You’ll report directly to the Director of Engineering, working closely with cross-functional partners across engineering, product, design, and leadership. You’ll be trusted to take on complex, cross-cutting business problems—not just scoped projects—and lead them from problem definition through implementation. You won’t manage people, but you will lead through influence, technical authority, and delivery. This is a hands-on role: you’ll spend a significant portion of your time writing production code, prototyping solutions, exploring new technologies, and jumping into unfamiliar systems to unblock teams. We expect Principal Engineers to be fluent in AI-assisted software development and agentic workflows, using them as a natural part of modern engineering practice to move faster, explore more solutions, and create greater leverage across the organization while maintaining thoughtful, durable engineering standards. This is not a traditional software engineering role. Successful candidates will already be operating at the forefront of AI-accelerated development, using modern tooling to amplify their impact, move seamlessly across large codebases and domains, and deliver outcomes that would have previously required significantly larger teams or longer timelines. Responsibilities: Technical Strategy & Architecture Lead architecture, design, and delivery of critical capabilities across Drake Tax Online, balancing customer experience, platform scalability, reliability, security, and long-term maintainability. Drive consistency and quality across services, APIs, user experiences, and shared platform components by establishing engineering standards and championing pragmatic best practices. Partner with product, design, and business stakeholders to translate complex customer and business problems into scalable, maintainable technical solutions. Identify, evaluate, and apply emerging technologies—including AI-assisted development tools and agentic workflows—where they create meaningful advantages in engineering effectiveness, product quality, or customer outcomes. Lead foundational modernization initiatives across the platform, including architecture evolution, performance optimization, developer experience improvements, and reduction of technical debt. Ensure architectural decisions support the long-term scalability, operability, and evolution of Drake Tax Online while enabling teams to move quickly and deliver value with confidence. Cross-Team Engineering Leadership Act as a technical lead for high-impact initiatives that span multiple teams and disciplines, working from first principles to define, scope, and solve complex business and technical problems. Provide technical leadership in ambiguous situations, bringing clarity, alignment, and momentum to initiatives without relying on formal authority. Balance strategic thinking with deep implementation—you'll often be the first to prototype a solution, evaluate a new approach, or dive into an unfamiliar system to uncover root causes and unblock teams. Serve as a trusted advisor to engineering leaders and senior engineers, providing mentorship, design guidance, and pragmatic feedback on critical technical decisions. Partner closely with product, design, infrastructur