Principal Software Engineer, AI-Augmented Development

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.

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, infrastructure, security, and quality engineering teams to ensure solutions are scalable, observable, reliable, and secure.

• Raise the effectiveness of the broader engineering organization by identifying opportunities to simplify systems, improve development workflows, and increase engineering leverage.

AI-Native Engineering

• Demonstrate what highly effective AI-assisted software engineering looks like in practice, using coding agents, AI-powered development tools, and agentic workflows to accelerate delivery and increase engineering leverage.

• Apply AI-assisted development responsibly, maintaining accountability for the correctness, security, performance, maintainability, and operational readiness of delivered software.

• Identify opportunities to use AI to improve engineering effectiveness across the software development lifecycle, including design, implementation, testing, documentation, debugging, and operational support.

• Evaluate emerging tools, workflows, and practices, providing pragmatic guidance on what should be adopted, standardized, scaled, or avoided.

• Help teams develop effective patterns for reviewing, testing, validating, and maintaining AI-assisted work while preserving strong engineering fundamentals and sound technical judgment.

• Raise the overall effectiveness of the engineering organization by helping engineers incorporate AI-native development practices into their daily work.

Qualifications:

Experience

• 10+ years of professional software engineering experience, with deep experience delivering and operating complex software systems at scale.

• Proven track record leading large technical initiatives across multiple teams, particularly in platform-critical, customer-facing, or business-critical domains.

• Demonstrated ability to operate across engineering, product, design, security, QA, DevOps, and business stakeholders to shape solutions that align technical investments with customer and business outcomes.

• Experience defining technical direction, influencing architecture, and delivering complex systems through technical leadership rather than formal authority.

• Demonstrated effectiveness using AI-assisted development tools, coding agents, and agentic workflows as part of day-to-day software engineering practice.

• Experience modernizing legacy systems, reducing technical complexity, and driving platform evolution while maintaining operational stability.

• Strong track record of turning ambiguous business problems into well-defined technical solutions and delivering measurable results.

Technical Expertise

• Significant production experience building and operating modern web applications, with the ability to contribute effectively across frontend, backend, platform, and cloud infrastructure domains.

• Strong hands-on coding ability. You deliver production-grade code regularly and effectively, whether delivering new capabilities, modernizing legacy systems, building shared tooling, or rapidly validating ideas through prototypes.

• Deep understanding of modern software architecture, including distributed systems, APIs, asynchronous workflows, event-driven systems, CI/CD, observability, security, and cloud-native application design.

• Experience designing, deploying, operating, and troubleshooting applications in AWS and Kubernetes-based production environments.

• Ability to quickly understand unfamiliar systems, identify root causes, and navigate complex technical problems that span application, infrastructure, data, and third-party boundaries.

• Demonstrated ability to effectively leverage AI-assisted development tools and agentic workflows while maintaining ownership of architecture, implementation quality, security, operational readiness, and long-term maintainability.

• Strong technical judgment with the ability to evaluate tradeoffs, challenge assumptions, and make pragmatic decisions that balance speed, risk, and long-term platform health.

Mindset & Communication

• You treat business outcomes as your scope, taking ownership of problems from identification through delivery rather than waiting for fully defined solutions.

• You are hands-on, pragmatic, and proactive. You seek out ambiguity, navigate complexity, and create clarity where others see uncertainty.

• You communicate effectively across technical and non-technical audiences, adapting your message to influence decisions, align stakeholders, and drive action.

• You are comfortable challenging assumptions, facilitating principled debate, and helping teams make sound decisions in the face of competing priorities and imperfect information.

• You elevate those around you through mentorship, technical leadership, thoughtful feedback, and a commitment to shared success.

• You value pragmatism, accountability, continuous learning, and high standards, balancing speed and execution with long-term platform health.

• You embrace new technologies, tools, and ways of working, continuously refining your approach to maximize impact for customers, teammates, and the business.

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 HR@Taxwell.com  or by calling 828-349-5887 to speak with a member of the HR Talent Acquisition team.