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.
What you'll do
Own and evolve complex, user-facing product areas end-to-end - from product definition and system design to implementation, launch, and iteration
Partner closely with product, design, and engineering leadership to shape roadmap decisions and translate ambiguous problems into durable solutions
Lead high-leverage initiatives that span frontend, backend, and data concerns, setting clear technical direction and guiding execution
Make thoughtful tradeoffs between user experience, system complexity, and delivery speed in a fast-moving product environment
Raise the bar on product quality, system correctness, and engineering craft across the stack
Act as a force multiplier for the team: reviewing designs, mentoring engineers, and unblocking others
What we're looking for
Significant experience building and owning product systems end-to-end, with depth in either frontend (JavaScript, React/React Native) or backend (Python)
Strong working fluency across the stack, with the ability to lead product work beyond your primary area of expertise
A product-minded approach to engineering — you care deeply about user outcomes, not just technical elegance
Proven ability to operate in ambiguity: framing problems, proposing options, and guiding teams toward pragmatic solutions
Strong communication skills and the ability to influence technical and product direction across disciplines
Experience mentoring engineers and raising team-wide technical quality (people management not required)
Nice to have
Experience working on marketplace, fintech, or data-sensitive products
Background in scaling early-stage products or evolving systems as usage grows
Interest in shaping engineering practices and standards as the team scales
Engineering @ WorkWhile
We’re a small and mighty team with senior engineers from Rippling, Stripe, DoorDash, Faire among others
We value user-centricity, competence, speed, and having fun
We embrace independence and take ownership of our projects, yet are also great team players
We deal in outcomes, not projects
Read more about our team at https://tech.workwhile.ai/
Benefits & Perks
Hybrid work culture with office hubs in SF, NY, Seattle & 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.
Top Skills
WorkWhile Toronto, Ontario, CAN Office
Toronto, ON, Canada
