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 backend systems that power core product flows, from architecture and data modelling to reliability and long-term scalability
Partner closely with engineering leadership, product, and design to shape technical direction and translate ambiguous problems into durable solutions
Lead high-impact initiatives that span multiple services or teams, setting clear technical direction and unblocking others
Raise the bar on system design, correctness, and operational excellence across the backend codebase
Act as a force multiplier for the team: reviewing designs, mentoring engineers, and helping others make strong technical decisions
Contribute to our engineering culture by modelling thoughtful tradeoffs, clear communication, and ownership at scale
What we're looking for
Significant experience designing and building backend systems in Python (or similar), including APIs, data models, and distributed services
A strong track record of owning technical systems or product areas end-to-end, especially in growing or evolving codebases
Comfort working in ambiguity: able to define problems, propose options, and guide teams toward pragmatic solutions
Deep care for system correctness, reliability, and long-term maintainability, balanced with real product needs
Strong written and verbal communication skills, with the ability to influence technical direction across the team
Experience mentoring engineers and elevating team-wide technical quality (formal management experience not required)
Nice to have
Experience working in marketplace, fintech, or data-sensitive systems
Exposure to scaling systems, migrations, or meaningful architectural change
Interest in helping shape engineering standards and best practices as the team grows
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
