Staff Software Engineer - Infrastructure

The Work

Engineering is the core of Check. We believe payroll should be simple modern financial software but building it requires deep infrastructure and systems thinking. 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. 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.

In this role you will:

• 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

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:

• 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 TypeScript 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

Travel and Office Policy

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.

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 all 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 $225000 and $247500.

• For all other locations the expected range is between $214000 and $235400.