Staff Software Engineer - Infrastructure
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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 $225,000 and $247,500.
For all other locations, the expected range is between $214,000 and $235,400.
Staff Software Engineer - Infrastructure
To see similar active jobs please follow this link: Remote System Administration jobs
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 $225,000 and $247,500.
For all other locations, the expected range is between $214,000 and $235,400.