Staff Software Engineer, Infrastructure

At Check, we make paying people simple. In doing that, we’re not just building our own business— we’re building payroll businesses together with every one of our partners. As the inventors of embedded payroll, we’re redefining how people get paid and making it easier for payroll businesses to launch, grow, and thrive. Check out the full story | Tune in.

Check is far more than just API infrastructure. We’re a springboard for building and scaling payroll businesses.

Payroll is broken. Come fix it alongside a team that’s as passionate as you are! At Check, you'll use creative problem-solving, critical thinking, and grit to impact every business we build. We view problems to solve and jobs to be done as opportunities to contribute to the solution; we ignore conventional role boundaries in favor of the unique strengths and value each builder brings to our team and to our mission.

Join us if you’re ready to roll up your sleeves and redefine payroll. Let’s simplify the complex, make a real impact, and create a better future for businesses of every size.

Engineering is the core of Check. We believe payroll should feel like modern financial software, and delivering that experience requires deep systems thinking and infrastructure that operators and partners can trust. Every product we ship depends on reliable, scalable, and secure systems that move money and deliver paychecks on time.

We’re looking for a Staff Software Engineer who combines strong software design skills with hands-on infrastructure experience. In this role, you’ll work on the foundational systems that power every payroll run, improving how we scale our services, operate them in production, and give engineers the tools to ship software safely and confidently.

You’ll work across product and platform areas to evolve our cloud infrastructure, strengthen how we deploy and observe systems, and simplify the architecture that powers embedded payroll. The problems you tackle will often sit at the intersection of infrastructure, product, and operations.

This role is ideal for someone who has owned complex systems end-to-end in fast-paced environments and who takes pride in building infrastructure that is resilient, understandable, and foundational to how the business runs.

• Design and evolve the systems that power every payroll run, the infrastructure responsible for moving money, calculating taxes, and ensuring payroll runs reliably at scale.
• Run at scaling and reliability challenges across our platform, improving how systems behave as our partners and payroll volumes grow.
• Simplify infrastructure and architecture over time by identifying bottlenecks, reducing operational complexity, and making systems easier for engineers to reason about.
• Improve how engineers build and ship software by strengthening CI/CD, observability, and developer tooling across the platform.
• Take ownership of key technical outcomes from initial design through production rollout and ongoing operation.
• Work with leaders during company planning cycles to discuss technical improvements we need to make
• Partner closely with product and engineering teams to deliver technical solutions that unlock new product capabilities.
• Work in the open by sharing context, writing clear technical proposals, and helping teams align around thoughtful solutions.
• Raise the engineering bar by mentoring teammates, sharing knowledge, and helping the team build systems we’re proud to operate.

• Python / Django for our API
• React and TypeScript for our frontends
• AWS and Terraform for our cloud infrastructure
• Postgres / RDS for our database
• Temporal for workflow orchestration
• GitHub for issue tracking and CI/CD

• Experience working in startup environments where engineers own infrastructure as well as product systems.
• Experience designing and operating complex systems that have scaled or evolved significantly over time.
• Hands-on experience with AWS, Terraform, Docker, and modern CI/CD systems.
• Strong systems design skills and a track record of building reliable, maintainable services.
• Comfort debugging complex production issues and improving systems through thoughtful simplification.
• Proficiency in Python (experience with TypeScript or React is a plus).
• Ability to bring clarity to ambiguous technical problems and help teams align on practical solutions.

The Check team is distributed across the US, with offices in New York City and San Francisco. While we embrace remote work, we believe time together is where we lay the groundwork for our yearlong collaboration. We offer ample opportunities and encourage employees to attend team off-sites, events, and hackathons a couple of times a year! We expect all employees to attend our annual 3-day company retreat each spring.

For our in-office and hybrid employees, our offices are open all week. We provide meals on Tuesdays and Thursdays, and the team hosts regular happy hours, game nights, and other social events.