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.

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.

We’re looking for a Staff Software Engineer who combines strong software design skills with hands-on infrastructure experience. You’ll design and build the systems that power every payroll run, from scaling our core services to improving how we deploy, monitor, and operate them in production. You’ll work across product and platform areas, helping evolve our cloud infrastructure, strengthen CI/CD, and make it easier for every engineer at Check to build and ship software with confidence.

This role is ideal for someone who has built and owned complex systems end-to-end in fast‑paced environments and who takes pride in building systems that are simple, resilient, and foundational to how embedded payroll works at scale.

• Design and scale the systems that move money, file taxes, and power every product we build
• Drive improvements across infrastructure, reliability, and developer experience
• Lead projects that simplify our architecture and increase performance as we grow
• Shape how Check builds software by improving CI/CD, observability, and developer tooling
• Own key technical outcomes end-to-end, from design through production rollout
• Collaborate closely with other teams to deliver technical solutions that unlock business goals
• Share knowledge openly, mentor others, and contribute to a culture of ownership and learning

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

• Background working in startup environments where engineers own their own infrastructure and ship product code
• Staff-level experience setting technical direction and delivering impact across multiple teams
• Deep 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
• Proficiency in Python and experience with Type Script or React is a plus
• Strong debugging skills and the ability to simplify complex systems over time
• Ability to set direction and rally others around clear technical goals

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 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, and other social events.

For full‑time employees, Check offers stock options, flexible PTO and sick leave, 16 weeks of fully paid parental leave for all new parents, flexible…