Job description

ABOUT CHECK Payroll is broken. It's still running on decades-old infrastructure. We're rebuilding it. We don't run payroll ourselves — we power the businesses that do. As the inventors of embedded payroll, we're redefining how people get paid and making it easier for those businesses to launch, grow, and thrive. On our team, you'll use creative problem-solving, critical thinking, and grit to simplify the complexity of payroll for thousands of employers of every size, across all industries. We ignore conventional role boundaries in favor of the unique strengths and values each builder brings to our mission: make paying people simple. Check out our origin story! app.notion.com Check is far more than just API infrastructure. We’re a springboard for building and scaling payroll businesses. See how it works for our partners. checkhq.com Engineering Culture at Check Engineering at Check works as one small team with a lot of ownership. We staff engineers on business priorities rather than fixed domains, and when something is stuck, people step in to move it forward instead of waiting on ownership boundaries. AI is central to how we build, and very little of our code is written by hand. That makes engineering judgment more important: deciding on the right problems to solve, defining what "done" means, and working with AI to get there. A merged PR isn't the finish line. The work is done when it has had the intended outcomes. About this role As a staff engineer, you'll use technical depth, product sense and AI tools to take on the hardest, highest-impact problems on the platform that moves money, calculates taxes and runs compliance for thousands of businesses. You'll decide what's worth solving, then see it through, often over several months and across teams, so our partners can run payroll confidently and thousands of people get paid. What You'll Do - Own company-level outcomes from start to finish, including identifying the problems worth solving, defining the impact you're aiming for, and driving multi-month efforts through rollout and follow-through - Set technical direction for complex, cross-team systems, making architecture decisions that hold up as we scale - Use AI to research, prototype and build quickly, and own the quality of everything you ship, however it was written - Set the bar for how engineering builds with AI across teams, including review standards, workflows and where human judgment can't be skipped - Simplify our platform by spotting patterns across domains, reducing complexity and questioning the status quo, including when it's your own past work - Make clear, well-reasoned decisions under ambiguity, and write down the thinking so others can build on it - Raise the quality bar across engineering through reviews, candid feedback and mentorship, and help grow senior engineers into broader scope - Work with product, operations and partners to understand problems directly from the people who have them, and turn them into business outcomes What We're Looking For - Staff-level experience building and operating complex systems, ideally at scale or in a regulated industry, with a track record of driving outcomes that moved the business, not just a team - Experience leading efforts that took months, not weeks, and delivering on them by chipping away at hard, ambiguous problems - Deep, hands-on experience building with AI tools, with clear opinions on where they help, where they fall short, and when to override them - The ability to work autonomously on company-wide projects, set your own priorities, and bring others along without relying on formal authority - A track record of fast, sound decisions grounded in experience, including knowing when to go deep and when to ship - The curiosity and persistence to debug complex problems in intricate systems - Comfort working cross-functionally with internal teams and partners, and influencing across them We don't require any particular programming language. You'll pick up our stack (Python/Django, React, TypeScript, AWS, Terraform, Postgres, Temporal, GitHub) as you go. TRAVEL & OFFICE POLICY The Check team is distributed across the US. Roles can be remote, hybrid, or based in one of our offices in New York City or San Francisco. We offer ample opportunities and encourage employees to attend team offsites, events, and hackathons throughout year. All Checketeers gather in the spring for our annual 3-day company retreat. For our in-office and hybrid employees, our offices are open all week. We provide meals on Tuesdays and Thursdays and there are regular happy hours, game nights, and other in-person events. Remote work at Check requires the ability to perform all responsibilities without distraction or disruption, while maintaining quality, effective communication, and productivity. -- Check is proud to be an Equal Opportunity employer. We do not discriminate based on race, religion, color, national origin, sex (including pregnancy, childbirth, or related medical conditions), sexual orientation, gender, gender identity, gender expression, transgender status, sexual stereotypes, age, status as a protected veteran, status as an individual with a disability, or other applicable legally protected characteristics. We also consider qualified applicants with criminal histories, provided they are consistent with applicable federal, state, and local laws. Check is committed to providing reasonable accommodations for candidates with disabilities in our recruiting process. Check participates in E-Verify and will provide the federal government with Form I-9 information from all new employees to confirm that they are authorized to work in the U.S. Check does not use E-Verify to pre-screen applicants.

Requirements

Must-haves

Own company-level outcomes from start to finish, including identifying the problems worth solving, defining the impact you're aiming for, and driving multi-month efforts through rollout and follow-through
Set technical direction for complex, cross-team systems, making architecture decisions that hold up as we scale
Use AI to research, prototype and build quickly, and own the quality of everything you ship, however it was written
Set the bar for how engineering builds with AI across teams, including review standards, workflows and where human judgment can't be skipped
Simplify our platform by spotting patterns across domains, reducing complexity and questioning the status quo, including when it's your own past work
Make clear, well-reasoned decisions under ambiguity, and write down the thinking so others can build on it
Raise the quality bar across engineering through reviews, candid feedback and mentorship, and help grow senior engineers into broader scope
Work with product, operations and partners to understand problems directly from the people who have them, and turn them into business outcomes
Staff-level experience building and operating complex systems, ideally at scale or in a regulated industry, with a track record of driving outcomes that moved the business, not just a team
Experience leading efforts that took months, not weeks, and delivering on them by chipping away at hard, ambiguous problems
Deep, hands-on experience building with AI tools, with clear opinions on where they help, where they fall short, and when to override them
The ability to work autonomously on company-wide projects, set your own priorities, and bring others along without relying on formal authority
A track record of fast, sound decisions grounded in experience, including knowing when to go deep and when to ship
The curiosity and persistence to debug complex problems in intricate systems
Comfort working cross-functionally with internal teams and partners, and influencing across them
We don't require any particular programming language. You'll pick up our stack (Python/Django, React, TypeScript, AWS, Terraform, Postgres, Temporal, GitHub) as you go.
For our in-office and hybrid employees, our offices are open all week. We provide meals on Tuesdays and Thursdays and there are regular happy hours, game nights, and other in-person events.
Remote work at Check requires the ability to perform all responsibilities without distraction or disruption, while maintaining quality, effective communication, and productivity.

Nice-to-haves

None flagged.

Application prep

Use the role’s language and application details while tailoring your materials.

Keywords to mirror

apiaigopythonreacttypescriptawspostgres

Platform: ashby
Effort: quick