Principal Product Designer

Drake Software is focused on providing tax advantages to everyday Americans through their software. They are seeking a Principal Product Designer to advance the product design discipline, particularly in AI, while collaborating with product management and engineering to enhance user experiences and solve complex problems.

Responsibilities:

• 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
• 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
• 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
• 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
• 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
• 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
• 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

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
• 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, explainability, 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