Principal Product Designer

TAXWELL•Haverford, PA

About The Position

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. 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.

Requirements

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

Nice To Haves

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

Responsibilities

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