Principal Product Designer

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. Taxwell is a leading digital tax filing platform formed in 2022 from the combination of Drake Software® and TaxAct®. These two longstanding organizations offer customers professional and do-it-yourself digital and downloadable products that are easy-to-use, best-in-class technology, and provide unparalleled customer support. Taxwell brands are a trusted solution for all users including those with complex tax returns. We strive to attract and retain candidates who exemplify our values: performance, perseverance, progress and partnership. Taxwell is an organization of forward thinkers looking to add industry experts to our growing team. Position Summary Taxwell is looking to hire a Principal Product Designer to join our mission of making it affordable and easy for individuals and businesses to digitally file their taxes. This individual will advance the product design discipline, including defining how the organization designs with and for AI, to elevate our experience. They will collaborate closely with product management and engineering teams to deliver superior experiences that solve complex problems, achieve business impact, and elevate customer outcomes. For this role, we expect a transformative level of AI fluency to help re-engineer how work happens. What You’ll Do Design Quality & Craft Define user experiences and interfaces for product prototypes in keeping with industry standards and best practices Translate user needs and business requirements into compelling experiences and strategies across complex, multi-touchpoint journeys Create user journeys, user flows, and interactive prototypes across multiple customer journeys and interfaces Ability to use vibe coding tools to communicate in code while establishing patterns and best practices AI-enabled Product Design Define the organization’s approach to designing AI-powered products and features, establishing frameworks, patterns, and principles that guide how AI is experienced by users Design innovative product features that leverage generative AI to transform how users discover, complete, and engage with tax filing Establish design principles and interaction patterns for AI-native experiences that scale across multiple surfaces and products Strategy & Influence Advise senior leaders on design initiatives, strategies, and the strategic role of AI in the product experience Lead the development of product design best practices, templates, and trainings to increase design knowledge and standards for the organization, with a focus on AI-native design methodologies Define metrics to manage and measure design success and prioritize enhancements Cross-Functional Collaboration Collaborate with product management, engineering, and data to shape product roadmaps and prioritize features Partner with product and engineering leadership to shape the company’s AI product strategy and roadmap Storytelling & Communication Develop and communicate product vision through storytelling, high-fidelity prototypes, and working software to leadership and cross-functional partners Excel at delivering compelling and impactful presentations, setting the example for how to use storytelling to influence and persuade others Mentorship & Organizational Development Collaborate with leadership to support team member development, including AI skill-building across the design organization Mentor and elevate design quality across the team through design reviews, feedback, and craft leadership Build and facilitate AI design training programs that upskill the entire design team AI Fluency Expectations For this role, we expect a transformative level of AI competency to help re-engineer how work happens. You will shape new ways of building products and can show examples of redesigning how products ship. You don’t just use AI, you fundamentally rethink how the design discipline operates in an AI-native world. You abandon the status quo when it no longer serves, and you lead others through that transformation with conviction and clarity Define the vision for how AI transforms the design practice at Taxwell, from tools and workflows to the products we build for customers. Evaluate emerging AI capabilities (LLMs, multimodal models, agentic AI) and translate them into actionable product and design opportunities. Lead cross-functional initiatives that create competitive differentiation Build systems, not one-off features, pipelines and agent-driven workflows that take in customer feedback, generate specs, prototype solutions, and ship. Build and facilitate AI training programs that upskill the entire design team. Lead new ways of building product, such as unlocking designers to ship code in production Establish organizational quality standards for AI-augmented work. Define guardrails for AI-powered experiences that balance innovation with user trust and ethical considerations. Own the outcomes at the organizational level, not just your own work, but the quality bar for how AI is used across the design team and larger organization Who You Are Bachelor’s degree or equivalent expertise in User Experience, Interaction Design, Communication Design, Information Architecture, Psychology, Human-Computer Interaction, Human Factors, or a related field 10+ years of experience or equivalent expertise designing solutions for software, web applications, or mobile native apps 8+ years of experience or equivalent expertise using industry-standard design and prototyping tools to create low- and high-fidelity designs and define the wor