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 work
- Deep proficiency with AI-powered design tools and workflows, with a track record of integrating AI capabilities into the design process and championing adoption across teams
- Demonstrated experience designing AI-powered products or features at scale—including conversational AI, intelligent automation, agentic workflows, personalization engines, or predictive experiences with proven ability to ship to production with real outcomes
- Demonstrated expertise defining success criteria and key performance indicators (KPIs) used to measure design effectiveness
- Demonstrated experience influencing, negotiating with, and gaining buy-in from stakeholders, including executive leadership
- Demonstrated ability to develop an experience design discipline for an organization, including creation and facilitation of trainings, establishing design standards, and tool enablement
- Excels at delivering compelling and impactful presentations and sets the example for how to use storytelling to influence and persuade others
- Ability to work independently on multiple concurrent projects and provide mentorship to other designers
- Ability to facilitate conversations and drive outcomes across the business
- Can show examples of redesigning how product ships: abandoning the previous status quo and reinventing the process with AI at the core
- Resume must include a link to your design portfolio
Preferred Qualifications
- Master’s degree in User Experience, Interaction Design, Communication Design, Information Architecture, Psychology, HCI, Human Factors, or a related field
- Demonstrated ability working with SaaS consumer products
- Experience defining AI design strategy for an organization including establishing when and how AI should be integrated into user experiences
- Proficiency with vibe coding and ability to lead teams that use AI-assisted development tools to accelerate design-to-development workflows
- Experience with responsible AI design practices including bias mitigation, explain ability, and inclusive design for AI-driven experiences
- Thought leadership in the AI design space through conference talks, published writing, or recognized contributions to the design community
- Experience unlocking designers to ship code in production, with a clear understanding of the tradeoffs involved
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.
