Lead Product Designer

WorkWhile

WorkWhile

Product, Design
Canada
Posted on Sep 8, 2025

About WorkWhile

WorkWhile is on a mission to help workers earn a better living and live better lives. More than 80 million Americans work hourly jobs, often with unpredictable schedules that pay close to minimum wage and offer limited benefits, leading to financial instability.

WorkWhile is revolutionizing frontline work by creating a more flexible and efficient labor market. Powered by AI, the WorkWhile platform helps businesses quickly access high-quality talent. Workers benefit from same-day pay, free telehealth services, upskilling, and the ability to choose shifts that match their skills and schedules.

We have the audacious goal to align incentives and solve inefficiencies in the labor market, disrupting the $650 billion staffing and recruiting market. Backed by Khosla Ventures and recognized by the Inc. 5000 for 10x growth, WorkWhile is reshaping the future of work.

About the role

As a Lead Product Designer at WorkWhile, you’ll drive end-to-end design for high-impact initiatives, creating intuitive experiences that empower hourly workers and help businesses thrive, and embedding design excellence and user-centered thinking into every part of how we build, collaborate, and ship.

What you’ll do

  • Shape our product strategy and play a key role in decisions about product direction

  • Lead end-to-end design projects, participate in design critiques, and collaborate closely with engineers and other key stakeholders to ensure seamless implementation

  • Develop features and improvements that ship with speed and exceptional quality

  • Design flows, prototypes, and high-fidelity visuals that bring your features to life

  • Contribute to team growth by supporting hiring efforts and fostering a design-centered culture

  • Help establish foundational processes that emphasize our commitment to detail and a design-centric approach

What we’re looking for

  • A genuine passion for crafting exceptional design solutions for UX, UI, and interaction challenges

  • A strong portfolio showcasing top-tier product designs created in fast-paced environments

  • Strong product sense, with an ability to deeply understand user needs

  • Strategic thinking around complex interaction design, with a focus on user-centered solutions

  • Skill in visualizing ideas through sketches, wireframes, and prototyping (we primarily use Figma)

  • Familiarity with design systems and technical tools

  • A high standard for visual, UI, and interaction quality

Benefits & Perks

  • Remote work culture with opportunities for co-working in SF & Toronto

  • In-person company offsites

  • Medical, dental, & vision coverage

  • Flexible time off

  • 401(k) with employer match

  • WFH stipend to support your home office needs

WorkWhile has a diverse, mission-driven, and supportive culture—we look for people who want to take ownership, are energized by ambiguity, and strive to make a lasting impact. If this resonates with you, we’d love to chat!

WorkWhile is an Equal Opportunity Employer. Women, minorities, individuals with disabilities and protected veterans are encouraged to apply.