Staff Software Engineer, Infrastructure

Building at Check

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.

Our Team

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.

The Work

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.

In this role, you will:

• 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.

Our Stack

• 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

Many backgrounds could fit this role, but ideal candidates will have some or all of the following:

• 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.

What we offer:

For full-time employees, Check offers stock options, flexible PTO and sick leave, up to 16 weeks of fully paid parental leave for new parents, flexible return-to-work, 9 annual holidays, a 401 (k) retirement plan, and a $100 monthly stipend for home internet and mobile phone expenses. We also provide high-quality medical, dental, vision, short-term/long-term disability, and basic life insurance coverage, effective on your first day of work.

At Check, transparency and fairness in compensation are our top priorities: our compensation bands are visible to all employees across all roles. The actual annual salary for this role is dependent on each candidate’s experience, qualifications, and work location:

• In San Francisco, NYC, LA, and Seattle, the expected range is between $225,000 and $247,500.

• For all other locations, the expected range is between $214,000 and $235,400.

We accept applications on an ongoing basis with no specified deadline.

Travel and Office Policy

This role can be remote, hybrid, or based in one of our offices in New York City or San Francisco. The Check team is distributed across the US! While we welcome remote work, personal time is valuable and important. We offer ample opportunities and encourage employees to attend team offsites, events, and hackathons a couple of times a year! All employees must be willing to attend our annual 3-day company offsite in the 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, etc.

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.