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)
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/
Responsibilities
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
Benefits
SF/NY/Seattle$150K – $250K • Offers Equity
TorontoCA$165K – CA$310K • Offers Equity
This range represents the good-faith estimate of the base salary/wage we reasonably expect to pay at the time of hire. Final offer amounts are determined by multiple factors, including seniority, experience, skills, and geography.
Upload your resume here to autofill key application fields.