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Sr. Product Designer
Sr. Product DesignerDealerware • Kingston (Downtown), Ontario, Canada, K7L
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Sr. Product Designer

Sr. Product Designer

Dealerware • Kingston (Downtown), Ontario, Canada, K7L
13 days ago
Job type
  • Full-time
Job description

Sr. Product Designer

About Dealerware
Dealerware transforms the automotive retailers of today into the mobility network of tomorrow. Launched in 2016, Dealerware manages tens of thousands of vehicles at dealerships in North America across every major manufacturer brand. Dealerware is committed to being a people-first culture and a great place to work for all, with flexible scheduling, unlimited PTO, extensive benefits, a core value of Diversity, Equity & Inclusion, and a leadership and management team that defaults to being supportive and accessible. In 2026, Dealerware was recognized by Built In as one of their Best Startups to Work for in Austin for the fifth consecutive year.

Digital experience is the connective tissue of Dealerware’s platform. Every day, thousands of dealership employees rely on Dealerware to execute contracting workflows across rental, loaner, test-drive, and pickup-and-delivery experiences all within one platform. We are trusted to translate high-stakes moments—scanning IDs, validating insurance, capturing vehicle damage, and completing mobile check-ins—into interactions that are secure, intuitive, and compliant, whether at the service drive or in a customer’s driveway.
As Sr. Product Designer, you will shape the experience that powers these intelligent interactions, transforming operational complexity into elegant, human-centered workflows that drive revenue, boost utilization, increase compliance, and build customer confidence. This role operates as a senior individual contributor with strategic visibility across the organization, influencing platform direction, design standards, and the long-term vision of Dealerware’s experience ecosystem.

As a Sr. Product Designer, you will:

  • Lead design across the full product development lifecycle, from discovery and concept definition through launch and iteration.
  • Immerse yourself in the real work by standing shoulder to shoulder with dealership teams in the service lane, identifying the friction that prevents them from doing their best work, and designing systems that help them show up as everyday heroes for their customers.
  • Design end-to-end service experiences, obsessing over every touchpoint across the customer lifecycle, including signup, onboarding, daily use, expansion, and new product adoption.
  • Design intelligent, AI-assisted workflows that reduce manual work, increase clarity, and build trust.
  • Use modern AI tooling such as Figma Make, Lovable, Cursor, and LLM copilots to accelerate exploration and prototyping while maintaining strong judgment and critical thinking.
  • Think in service systems by mapping journeys, states, roles, permissions, compliance logic, and edge cases across onboarding, contracting, daily operations, and expansion.
  • Thrive in divergent thinking before converging by exploring broadly, stress-testing assumptions, and narrowing based on real signal.
  • Facilitate high-impact workshops and design sessions, pulling from your toolkit (journey mapping, service blueprints, systems mapping, rapid prototyping) to align stakeholders around the right problem to solve.

What does success look like:

  • Help crack the code on dealership customer loyalty by deeply understanding the end consumer’s needs and designing confidence-building interactions that strengthen relationships and position the dealership as a long-term mobility partner beyond traditional service rental.
  • Transform contracting from a transactional workflow into a risk-intelligent control layer, enabling dealerships to better understand their customers, increase insurance verification coverage, safeguard fleet assets, and deliver elevated consumer experiences.
  • The platform aligns the needs of OEM partners, dealership teams, and end consumers, uncovering opportunities at their intersections and orchestrating a cohesive journey from onboarding through daily operations and expansion.
  • You establish a durable vision for Dealerware’s next generation of intelligent workflows and product experiences, influencing not only what we build, but how we build in an AI-accelerated world.

Your peers would say you:

  • Think in systems, not screens.
  • Bring clarity to ambiguity and structure to complexity.
  • Ask the questions that reframe the room, surface assumptions, expose unidentified risks, and focus the conversation.
  • Obsess over the full customer lifecycle, not just isolated moments.
  • Make smart tradeoffs grounded in research, testing, and metrics.
  • Leave teams, standards, and systems better than you found them.
  • Use AI and modern tooling as force multipliers.
  • Elevate conversations with frameworks, not opinions.
  • Care more about outcomes than ownership.

Required qualifications:

  • 7+ years of product design, UI/UX, or interaction design experience.
  • Bachelor’s degree in Design, HCI, or related field (or equivalent practical experience).
  • Portfolio showcasing product design leadership, conceptual strength, and polished execution across web and mobile workflows.
  • Deep understanding of UX best practices, information architecture, interaction design, and accessibility standards.
  • Mastery of industry-standard tools (e.g., Figma, Sketch; additional prototyping tools).
  • Experience building, contributing to, and maintaining scalable design systems and UI pattern libraries.

Even better if you have:

  • Experience designing automotive, fleet, rental, or subscription solutions
  • Experience designing identity verification, document intelligence, damage capture, insurance, or risk-reduction workflows.
  • Fluency in data visualization principles — designing reporting and dashboard systems that surface meaningful signals, minimize noise, and drive operational action.
  • Comfort navigating compliance, permissions, or multi-role complexity.
  • Working knowledge of front-end systems (React, Flutter, component architecture) a plus.

Dealerware offers you:

  • Competitive base salary with bonus incentive eligibility
  • Full benefits (medical, dental, vision, disability)
  • 401(k) with company match
  • On-demand educational courses via Learning
  • Tuition reimbursement and continuing education
  • Unlimited paid vacation policy
  • Flexible work
  • Generous Paid Parental Leave program
  • Modern office and a dynamic team in downtown Austin with free parking
  • Friendly, small company environment with a progressive culture
Dealerware is an Equal Opportunity Employer that does not discriminate on the basis of actual or perceived race, color, creed, religion, national origin, ancestry, citizenship status, age, sex or gender (including pregnancy, childbirth and pregnancy-related conditions), gender identity or including transgender status), sexual orientation, marital status, military service and veteran status, physical or mental disability, genetic information, or any other characteristic protected by applicable federal, state or local laws and ordinances. Dealerware's management team is dedicated to this policy with respect to recruitment, hiring, placement, promotion, transfer, training, compensation, benefits, employee activities, access to facilities and programs and general treatment during employment.

*We are interested in every qualified candidate who is eligible to work in the United States. However, we are not able to sponsor visas.





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Sr. Product Designer • Kingston (Downtown), Ontario, Canada, K7L

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