[Remote] Principal Software Engineer, AI-Augmented Development

Note: The job is a remote job and is open to candidates in USA. Drake Software is a leading digital tax filing platform that provides easy-to-use products and unparalleled customer support. They are seeking a Principal Software Engineer to drive critical initiatives across Drake Tax Online, focusing on enhancing the platform's architecture, scalability, reliability, and performance while leading complex engineering solutions.

Responsibilities

• 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
• 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
• 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

Skills

• 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
• 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
• 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

Company Overview