Staff Software Engineer, Infrastructure

Check•New York, NY

54d•$214,000 - $247,500•Remote

About The Position

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 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.

Requirements

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
Strong debugging skills and the ability to simplify complex systems over time
Ability to set direction and rally others around clear technical goals

Nice To Haves

Proficiency in Python and experience with TypeScript or React is a plus

Responsibilities

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

Benefits

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 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.

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