[Remote] Principal Software Engineer, AI-Augmented Development

Note: The job is a remote job and is open to candidates in USA. Taxwell is a company that helps everyday Americans maximize their tax advantages through innovative software solutions. They are seeking a Principal Software Engineer to lead critical initiatives for Drake Tax Online, focusing on enhancing customer experience, platform architecture, and engineering practices, particularly in AI-assisted development.ResponsibilitiesLead architecture, design, and delivery of critical capabilities across Drake Tax Online, balancing customer experience, platform scalability, reliability, security, and long-term maintainabilityDrive consistency and quality across services, APIs, user experiences, and shared platform components by establishing engineering standards and championing pragmatic best practicesPartner with product, design, and business stakeholders to translate complex customer and business problems into scalable, maintainable technical solutionsIdentify, 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 outcomesLead foundational modernization initiatives across the platform, including architecture evolution, performance optimization, developer experience improvements, and reduction of technical debtEnsure architectural decisions support the long-term scalability, operability, and evolution of Drake Tax Online while enabling teams to move quickly and deliver value with confidenceAct 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 problemsProvide technical leadership in ambiguous situations, bringing clarity, alignment, and momentum to initiatives without relying on formal authorityBalance 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 teamsServe as a trusted advisor to engineering leaders and senior engineers, providing mentorship, design guidance, and pragmatic feedback on critical technical decisionsPartner closely with product, design, infrastructure, security, and quality engineering teams to ensure solutions are scalable, observable, reliable, and secureRaise the effectiveness of the broader engineering organization by identifying opportunities to simplify systems, improve development workflows, and increase engineering leverageDemonstrate 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 leverageApply AI-assisted development responsibly, maintaining accountability for the correctness, security, performance, maintainability, and operational readiness of delivered softwareIdentify opportunities to use AI to improve engineering effectiveness across the software development lifecycle, including design, implementation, testing, documentation, debugging, and operational supportEvaluate emerging tools, workflows, and practices, providing pragmatic guidance on what should be adopted, standardized, scaled, or avoidedHelp teams develop effective patterns for reviewing, testing, validating, and maintaining AI-assisted work while preserving strong engineering fundamentals and sound technical judgmentRaise the overall effectiveness of the engineering organization by helping engineers incorporate AI-native development practices into their daily workSkills10+ years of professional software engineering experience, with deep experience delivering and operating complex software systems at scaleProven track record leading large technical initiatives across multiple teams, particularly in platform-critical, customer-facing, or business-critical domainsDemonstrated ability to operate across engineering, product, design, security, QA, DevOps, and business stakeholders to shape solutions that align technical investments with customer and business outcomesExperience defining technical direction, influencing architecture, and delivering complex systems through technical leadership rather than formal authorityDemonstrated effectiveness using AI-assisted development tools, coding agents, and agentic workflows as part of day-to-day software engineering practiceExperience modernizing legacy systems, reducing technical complexity, and driving platform evolution while maintaining operational stabilityStrong track record of turning ambiguous business problems into well-defined technical solutions and delivering measurable resultsSignificant production experience building and operating modern web applications, with the ability to contribute effectively across frontend, backend, platform, and cloud infrastructure domainsStrong 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 prototypesDeep understanding of modern software architecture, including distributed systems, APIs, asynchronous workflows, event-driven systems, CI/CD, observability, security, and cloud-native application designExperience designing, deploying, operating, and troubleshooting applications in AWS and Kubernetes-based production environmentsAbility to quickly understand unfamiliar systems, identify root causes, and navigate complex technical problems that span application, infrastructure, data, and third-party boundariesDemonstrated ability to effectively leverage AI-assisted development tools and agentic workflows while maintaining ownership of architecture, implementation quality, security, operational readiness, and long-term maintainabilityStrong technical judgment with the ability to evaluate tradeoffs, challenge assumptions, and make pragmatic decisions that balance speed, risk, and long-term platform healthYou treat business outcomes as your scope, taking ownership of problems from identification through delivery rather than waiting for fully defined solutionsYou are hands-on, pragmatic, and proactive. You seek out ambiguity, navigate complexity, and create clarity where others see uncertaintyYou communicate effectively across technical and non-technical audiences, adapting your message to influence decisions, align stakeholders, and drive actionYou are comfortable challenging assumptions, facilitating principled debate, and helping teams make sound decisions in the face of competing priorities and imperfect informationYou elevate those around you through mentorship, technical leadership, thoughtful feedback, and a commitment to shared successYou value pragmatism, accountability, continuous learning, and high standards, balancing speed and execution with long-term platform healthYou embrace new technologies, tools, and ways of working, continuously refining your approach to maximize impact for customers, teammates, and the businessCompany OverviewTaxwell is a digital tax filing platform that offers tax preparation software solutions. It was founded in 2022, and is headquartered in Franklin, North Carolina, USA, with a workforce of 1001-5000 employees. Its website is https://taxwell.com.