Sr. Product Designer

📍 Job Overview

Job Title: Sr. Product Designer

Company: Dealerware

Location: Austin, TX

Job Type: Full-Time, Salaried

Category: Product Design / UX/UI

Date Posted: 2026-07-27

Experience Level: 5+ Years

Remote Status: Hybrid

🚀 Role Summary

• Lead the end-to-end user experience (UX) and user interface (UI) design for Dealerware's innovative platform, focusing on intuitive digital experiences for automotive workflows.

• Drive the evolution and ownership of Dealerware's comprehensive design system, ensuring consistency and scalability across mobile, tablet, and web interfaces.

• Leverage AI-first tools and methodologies to accelerate the design process, enabling rapid prototyping and near-production component generation.

• Collaborate closely with Product Managers and Engineering teams to elevate design velocity and quality, translating complex B2B SaaS requirements into user-centric solutions.

• Champion a data-driven design approach, defining success metrics, conducting user research, and utilizing analytics to validate design decisions and uncover new opportunities.

📝 Enhancement Note: This role is positioned as a Sr. Product Designer with significant autonomy and influence. The emphasis on "AI-first tools," "rapid prototyping," and "design system ownership" suggests a forward-thinking team that values efficiency and innovation. The focus on B2B SaaS and automotive workflows indicates a need for expertise in complex enterprise environments.

📈 Primary Responsibilities

• Own the complete UX and UI design lifecycle for critical dealership workflows, including vehicle check-in/out, mobile check-in, insurance verification, digital contracting, and fleet management.

• Design for the unique demands of a fast-paced service drive environment, considering factors like limited connectivity and user attention spans.

• Transform complex automotive data (fleet telemetry, tolls, insurance, DMS records) into streamlined and intuitive user workflows.

• Maintain and scale the Dealerware design system, ensuring a cohesive and polished user experience across all product surfaces.

• Develop interactive prototypes rapidly, utilizing AI-powered tools to accelerate ideation and validation cycles.

• Collaborate with Product Managers to define key performance indicators (KPIs) and success metrics for new features before design begins.

• Conduct user research, including interviews and usability testing, with a strong emphasis on rapid feedback loops and iterative design.

• Synthesize insights from various data sources, such as support tickets, NPS surveys, and session data, using AI tools for efficient analysis.

• Work closely with Engineering to ensure seamless implementation of designs, understanding technical constraints and leveraging component libraries effectively.

• Act as an internal evangelist for AI in design, sharing best practices, conducting workshops, and demonstrating the benefits of AI-augmented workflows.

• Empower Product Managers with design tools and systems to enable independent exploration and validation of ideas.

• Ensure visual polish and precision in all design deliverables, reflecting a high standard of craft.

📝 Enhancement Note: The responsibilities highlight a blend of strategic ownership (design system, platform direction) and tactical execution (rapid prototyping, workflow design). The expectation to "empower PMs" and "work in lockstep with engineering" underscores the collaborative and cross-functional nature of this role.

🎓 Skills & Qualifications

Education: While no specific degree is mandated, a strong portfolio and practical experience are paramount. A background in Design, Human-Computer Interaction, or a related field is beneficial.

Experience:

• Minimum of 5 years of experience in product design, interaction design, or UX design.

• At least 3 years of experience specifically within complex B2B SaaS, logistics, or enterprise software environments. Required Skills:

• Portfolio: A compelling portfolio demonstrating rapid iteration, exploration of multiple design directions, and the ability to showcase the process behind final screens.

• AI-First Workflow: Proven experience utilizing AI design tools (e.g., Claude, Cursor, Figma AI) as daily instruments for research, edge case analysis, and UX copy generation.

• Visual & Interaction Design: Strong fundamentals in visual design, interaction design, and user-centered design principles, with a track record of creating intuitive mobile-first, data-dense interfaces.

• Design System Expertise: Demonstrated experience in owning or significantly contributing to the development and evolution of a design system.

• Data Mindset: Ability to define, track, and analyze success metrics using product analytics to validate design decisions and identify new opportunities.

• Technical Acumen: Working knowledge of HTML, CSS, and component frameworks such as React or Tailwind. A strong appetite for editing UI code, potentially with AI assistants (e.g., Cursor), is highly valued.

• Workflow Simplification: A proven ability to transform complex, high-density data into simple, single-click workflows.

Preferred Skills:

• Experience designing specifically for automotive, fleet management, or logistics workflows.

• Prior experience working in a startup environment.

• Ability to write or generate light front-end code (React, HTML, CSS) using AI assistants to ship functional prototypes.

• Familiarity with AI-driven qualitative research synthesis techniques.

📝 Enhancement Note: The emphasis on "AI-first workflow" and "working knowledge of HTML, CSS, and component frameworks" with an "appetite for editing UI code" suggests a "product designer as a maker" role, bridging the gap between design and front-end development. The portfolio requirement specifically asks for "rapid iteration" and "work between the final screens," indicating a need to showcase process and iterative thinking.

📊 Process & Systems Portfolio Requirements

Portfolio Essentials:

• Showcase a strong emphasis on rapid iteration and exploration of multiple design directions, demonstrating the ability to move quickly from concept to validated prototype.

• Include case studies that illustrate the end-to-end design process, detailing problem definition, user research, ideation, prototyping, and iteration based on feedback and data.

• Highlight specific examples of how AI-first tools were integrated into the design workflow to enhance speed, efficiency, or quality.

• Present clear examples of owning or significantly shaping a design system, including its evolution, component library management, and application across different platforms.

• Demonstrate experience in translating complex, data-dense workflows into simple, intuitive user interfaces, particularly for mobile-first experiences. Process Documentation:

• Detail your approach to rapid prototyping, including the tools and methodologies used to quickly translate ideas into interactive experiences.

• Explain your process for defining and tracking design success metrics, and how you leverage product analytics and user data to validate decisions and iterate on designs.

• Outline your strategy for conducting user research (interviews, usability testing) with a focus on velocity and actionable insights.

• Describe your collaboration process with Product Managers and Engineering teams, emphasizing how you ensure alignment, communicate design intent, and facilitate smooth handoffs.

• Illustrate how you maintain consistency and scalability of design across different platforms (mobile, tablet, web) through design system ownership and documentation.

📝 Enhancement Note: The "portfolio that shows rapid iteration: multiple directions explored quickly, and the work between the final screens" is a critical requirement. This implies candidates should not just present final polished UIs but also the journey, including early concepts, wireframes, and usability testing outcomes. The mention of AI tools suggests showcasing how these were applied in the process.

💵 Compensation & Benefits

Salary Range: $140,000 - $160,000 USD per year.

Benefits:

• Competitive base salary with eligibility for bonus incentives.

• Comprehensive full benefits package: medical, dental, and vision insurance.

• Disability insurance coverage.

• 401(k) retirement plan with a company match.

• Access to on-demand educational courses through LinkedIn Learning.

• Support for continuous learning through tuition reimbursement and continuing education programs.

• Unlimited paid vacation policy, promoting work-life balance.

• Flexible work arrangements to accommodate personal needs.

• Generous Paid Parental Leave program.

• Modern office space in downtown Austin with free parking.

Working Hours: Standard full-time hours, likely around 40 hours per week, with flexibility offered.

📝 Enhancement Note: The salary range is provided, and the benefits list is extensive, highlighting a strong emphasis on employee well-being, professional development, and work-life balance, which is attractive for senior-level roles. The "unlimited paid vacation" and "flexible work" are key differentiators.

🎯 Team & Company Context

🏢 Company Culture

Industry: Technology, specifically SaaS for the automotive retail sector. Dealerware provides a platform to streamline various dealership operations like rentals, loans, test drives, and pickup/delivery contracting.

Company Size: Dealerware is a growing company, likely falling into the mid-size category (e.g., 200-500 employees based on typical tech company growth trajectories, though specific size not provided). This implies a dynamic environment with opportunities for impact but also established processes.

Founded: Founded in 2016, Dealerware is a relatively young company, suggesting a modern, agile, and potentially fast-paced culture focused on innovation and disruption in the automotive industry.

Team Structure:

• The Sr. Product Designer will be the sole design representative initially, reporting directly to the Sr. Director, Product Management.

• This role implies close collaboration with a team of Product Managers who cover mobile, tablet, and web platforms.

• Strong partnership with the Engineering team is crucial for successful implementation.

• The company emphasizes a "friendly, small company environment with a progressive culture." Methodology:

• AI-First Design: A core methodology involves leveraging AI tools (Claude, Cursor, Figma AI) for rapid ideation, prototyping, research synthesis, and code generation.

• Agile Development: The emphasis on rapid prototyping and iterative design suggests an agile or agile-like development process.

• Data-Driven Decisions: A commitment to defining success metrics, user research, and analytics to validate design choices.

• Design System Centricity: Focus on building and maintaining a robust design system for consistency and efficiency.

Company Website: https://dealerware.com/ (Assuming this is the correct domain based on context, though not explicitly provided in input)

📝 Enhancement Note: The company's focus on streamlining automotive workflows and its relatively recent founding suggest a culture that values innovation, efficiency, and a modern approach to technology. The "AI-first" mandate is a significant cultural and methodological differentiator for this role.

📈 Career & Growth Analysis

Operations Career Level: This is a Senior individual contributor role, focusing on deep expertise in Product Design, UX/UI, and Design Systems. It requires a high degree of autonomy and the ability to set design standards and long-term vision.

Reporting Structure: The Sr. Product Designer reports directly to the Sr. Director, Product Management. This structure offers high visibility to product leadership and allows for direct influence on product strategy.

Operations Impact: The role has a direct impact on Dealerware's core platform experience, which is described as the "connective tissue" of their business. By making the platform intuitive, secure, modern, and compliant, the designer influences:

• Revenue Generation: Streamlining contracting and check-in/out processes can lead to increased deal velocity and customer satisfaction.

• Customer Trust & Retention: A seamless and reliable digital experience builds trust and reduces churn.

• Operational Efficiency: Intuitive workflows reduce training time and errors for dealership employees.

• Compliance: Ensuring designs meet regulatory and industry standards.

Growth Opportunities:

• Design Leadership: Potential to grow into a Design Lead or Manager role as the design team expands, shaping the overall design strategy and mentoring junior designers.

• Specialization: Deepen expertise in AI-augmented design workflows, automotive tech, or complex B2B SaaS UX.

• Cross-Functional Influence: Expand influence across product strategy, engineering practices, and company-wide adoption of design thinking and AI tools.

• Direct Impact: Continue to drive significant product improvements and shape the user experience of a rapidly growing platform.

📝 Enhancement Note: The "high-autonomy individual contributor role with visibility across the company" indicates that career growth might focus on deepening expertise and expanding influence rather than immediate management progression, though leadership potential exists as the company scales.

🌐 Work Environment

Office Type: Dealerware offers a "modern office and a dynamic team in downtown Austin." This suggests a contemporary workspace designed for collaboration and productivity.

Office Location(s): Downtown Austin, TX, with the specific benefit of free parking.

Workspace Context:

• Collaborative Environment: The description "dynamic team" and "friendly, small company environment" points towards a collaborative and approachable atmosphere.

• Tools & Technology: The role heavily emphasizes the use of AI-first tools (Claude, Cursor, Figma AI) and modern design/development technologies (Figma, React, Tailwind). Expect access to a robust tech stack.

• Team Interaction: Opportunities for close working relationships with Product Managers, Engineers, and potentially other stakeholders across the company, facilitated by the downtown Austin office location.

Work Schedule: While standard full-time hours (approx. 40/week) are expected, the company offers "Flexible work," suggesting some degree of adaptability in daily schedules to support work-life balance and efficient workflow management.

📝 Enhancement Note: The combination of a modern downtown Austin office, free parking, and flexible work arrangements creates an attractive physical and operational environment for employees. The emphasis on AI tools implies a forward-thinking and tech-enabled workspace.

📄 Application & Portfolio Review Process

Interview Process:

• Initial Screening: A review of your resume and portfolio to assess basic qualifications and alignment with the role's core requirements, especially regarding AI usage and B2B SaaS experience.

• Portfolio Deep Dive: A dedicated session where you will walk through your portfolio, focusing on specific case studies that demonstrate rapid iteration, AI integration, design system ownership, and the transformation of complex data into intuitive workflows. Be prepared to discuss your process, decisions, and outcomes.

• Design Challenge/Exercise: You may be given a design problem or asked to complete a small exercise, potentially involving rapid prototyping or demonstrating AI tool usage, to assess your practical skills and approach.

• Cross-Functional Interviews: Meetings with Product Managers and potentially Engineering leads to evaluate your collaboration style, technical understanding, and ability to work within their established processes.

• Final Interview: Potentially with the Sr. Director, Product Management, to discuss strategic vision, cultural fit, and overall alignment with the company's goals.

Portfolio Review Tips:

• Highlight AI Integration: Clearly showcase how you've used AI tools (Claude, Cursor, Figma AI) in your projects. Explain the specific prompts, the outcomes, and how it accelerated your process or improved the design.

• Emphasize Process, Not Just Pixels: Since "rapid iteration" and "work between the final screens" are key, detail your thought process, research findings, failed attempts, and how you iterated based on feedback and data.

• Demonstrate Design System Ownership: If you've owned or significantly contributed to a design system, present its structure, evolution, and how you maintained consistency and scalability.

• Showcase Data-Dense Workflows: Include examples where you simplified complex data or processes into user-friendly interfaces, especially for mobile. Quantify the impact if possible (e.g., reduced task time, fewer errors).

• Prepare for Technical Discussion: Be ready to discuss your familiarity with HTML, CSS, React, or Tailwind, and how you approach collaborating with engineers.

Challenge Preparation:

• Familiarize yourself with Dealerware's existing product and user base. Understand the challenges of the automotive retail workflow.

• Practice rapid prototyping using tools like Figma, and be ready to incorporate AI assistance if applicable.

• Prepare to articulate your design thinking process clearly and concisely, focusing on user needs and business objectives.

• Think about how you would approach defining metrics for a new feature and using data to inform design decisions.

📝 Enhancement Note: The explicit mention of "rapid iteration" and "AI-first workflow" in the portfolio requirements is crucial. Candidates must be prepared to demonstrate these capabilities with concrete examples. The interview process will likely assess not just design skill, but also adaptability and proficiency with emerging technologies.

🛠 Tools & Technology Stack

Primary Tools:

• Design & Prototyping: Figma (with a strong emphasis on its component library and potential AI features), potentially other rapid prototyping tools.

• AI Design Assistants: Claude, Cursor, Figma AI (candidates are expected to be proficient and evangelize their use).

• User Research & Synthesis: Tools for user interviews, usability testing, and AI-driven synthesis of qualitative data.

Analytics & Reporting:

• Proficiency in using analytics platforms to track user behavior and validate design decisions. Specific tools not listed, but expect to work with product analytics data. CRM & Automation:

• While not directly a design tool, understanding the B2B SaaS context and potential integrations with CRM or workflow automation systems could be beneficial. Development Context:

• Front-End Technologies: Working knowledge of HTML, CSS, and component frameworks like React or Tailwind is required.

• Code Editing: Familiarity with editing UI code, potentially using AI coding assistants like Cursor.

📝 Enhancement Note: The explicit requirement for AI tools like Claude and Cursor, alongside a working knowledge of front-end code, positions this role as a "design technologist" or a highly integrated product designer. Proficiency in Figma and its advanced features (component libraries, design tokens) is foundational.

👥 Team Culture & Values

Operations Values:

• Innovation & Efficiency: A strong drive to leverage new technologies, particularly AI, to create more efficient and effective software solutions.

• Customer Centricity: A commitment to understanding and solving the complex needs of dealership employees and customers, ensuring intuitive and secure digital experiences.

• Collaboration: An emphasis on working closely with Product Management and Engineering, fostering a shared understanding and ownership of product goals.

• Autonomy & Ownership: Empowering individuals to take ownership of their domains, set standards, and drive direction, especially in a senior individual contributor role.

• Data-Informed Decisions: A belief in using metrics, research, and analytics to guide design choices and measure impact.

Collaboration Style:

• Cross-functional Integration: Close partnership with Product Managers to align on strategy and requirements, and with Engineering to ensure seamless implementation.

• AI Evangelism: A culture that encourages sharing knowledge and championing new technologies like AI to improve team velocity and product quality.

• Feedback-Driven: A willingness to engage in rapid feedback loops through user testing and iteration, with an open approach to receiving and giving constructive criticism.

• Empowerment: A philosophy of empowering team members, such as enabling Product Managers to prototype independently, fostering a collaborative and supportive environment.

📝 Enhancement Note: The company culture appears to be a blend of lean startup agility (rapid iteration, AI-first) and established B2B SaaS best practices (design systems, data-driven decisions, cross-functional collaboration). The "friendly, small company environment" suggests a close-knit team.

⚡ Challenges & Growth Opportunities

Challenges:

• Pace of Innovation: Keeping up with the rapid advancements in AI tools and integrating them effectively and ethically into the design workflow.

• Complexity of Workflows: Designing intuitive interfaces for dense, high-stakes automotive workflows that require precision and compliance.

• Solo Design Role: As the initial design lead, the challenge of single-handedly setting design standards, managing the design system, and supporting multiple product initiatives.

• Balancing Speed and Craft: Delivering rapidly with AI tools while maintaining a high level of visual polish and user experience quality.

• Cross-Functional Alignment: Ensuring buy-in and understanding of design principles and AI-driven workflows across Product and Engineering.

Learning & Development Opportunities:

• AI Design Mastery: Becoming an expert in leveraging AI for all facets of the design process, from research synthesis to code generation.

• Design System Leadership: Growing expertise in design system architecture, maintenance, and scaling, potentially shaping it into a company-wide asset.

• Automotive Tech Domain Expertise: Developing deep knowledge of the automotive retail industry and its unique operational challenges.

• Product Strategy Influence: Contributing significantly to the strategic direction of Dealerware's platform through user-centered design insights.

• Mentorship Potential: As the team grows, opportunities to mentor junior designers and shape the future design function.

📝 Enhancement Note: The primary challenge and opportunity lie in embracing and leading with AI-first design methodologies within a complex B2B domain. The success of this role will depend on the candidate's ability to innovate, adapt, and influence.

💡 Interview Preparation

Strategy Questions:

• "Describe a time you used AI tools to significantly accelerate your design process. What was the outcome, and what were the trade-offs?" (Focus on specific examples of Claude, Cursor, Figma AI).

• "How would you approach designing a mobile-first workflow for vehicle check-in that handles complex insurance verification and potential connectivity issues?" (Prepare to discuss user needs, data handling, and iterative design).

• "Walk us through a complex B2B SaaS feature you designed. How did you translate dense data into an intuitive user experience, and what metrics did you use to measure success?" (Highlight your portfolio's strongest case study).

• "How do you balance the need for rapid prototyping with maintaining high visual craft and a consistent design system?" (Discuss your methodology for speed vs. quality). Company & Culture Questions:

• "What are your thoughts on Dealerware's focus on AI-first design, and how do you see it evolving the product design field?" (Showcase your enthusiasm and understanding of AI in design).

• "How would you contribute to building and evolving our design system as the sole designer initially?" (Discuss your approach to ownership, scalability, and documentation).

• "Describe your ideal collaboration style with Product Managers and Engineers, especially when advocating for user-centered design or new AI tools." (Emphasize partnership and clear communication). Portfolio Presentation Strategy:

• Structure for Iteration: Organize your case studies to explicitly show the journey: problem statement, research, initial concepts, iterations based on feedback/data, and final solution.

• Quantify Impact: Where possible, use metrics (even if estimated) to demonstrate the value of your designs (e.g., improved task completion rates, reduced error rates, increased user satisfaction).

• Showcase AI Integration: Clearly mark and explain where and how AI tools were used in each project. Be ready to discuss prompt engineering and the specific benefits gained.

• Technical Readiness: Be prepared to discuss your comfort level with HTML, CSS, React, and how you collaborate with developers on implementation.

📝 Enhancement Note: Candidates should prepare to discuss AI tool usage extensively, as it's a core requirement. The portfolio presentation needs to go beyond final screens to demonstrate the iterative process and the "work between the final screens."

📌 Application Steps

To apply for this Sr. Product Designer position:

• Submit your application through the provided link on Dealerware's careers portal.

• Portfolio Customization: Tailor your portfolio to prominently feature projects showcasing rapid iteration, AI-first workflows, design system contributions, and experience with complex B2B SaaS or automotive/logistics applications.

• Resume Optimization: Ensure your resume highlights your 5+ years of relevant experience, specifically mentioning your proficiency with AI design tools (Claude, Cursor, Figma AI) and your background in B2B SaaS or enterprise software. Quantify achievements where possible.

• Interview Preparation: Practice articulating your design process, especially concerning rapid prototyping, AI integration, and design system ownership. Prepare to present your portfolio with a focus on the iterative journey and demonstrable outcomes.

• Company Research: Familiarize yourself with Dealerware's platform, target market, and recent company news. Understand their mission and how your design skills can contribute to their success in streamlining automotive workflows.

⚠️ Important Notice: This enhanced job description includes AI-generated insights and operations industry-standard assumptions. All details should be verified directly with the hiring organization before making application decisions.