Software Engineer, Staff

About Check

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 ignore conventional role boundaries in favor of the unique strengths and values each builder brings to our team, and our mission. We simplify the complex, make a real impact, and create a better future for businesses of every size.

About this role

As a Staff Software Engineer at Check, you’ll combine strong engineering fundamentals and close collaboration with cross-functional partners to build software that meaningfully improves how payroll businesses operate. You'll build the platform that powers money movement, tax calculations, and compliance workflows for thousands of businesses. By turning complex infrastructure into clear, reliable systems for our partners, you'll allow teams to run payroll confidently and help thousands of people get paid.

What You'll Do

• Run at complex problems across our platform, designing and building products that translate complex payroll infrastructure into intuitive tools for operators and partners.

• Own projects end-to-end, from identifying the problem and shaping the solution through design, implementation, rollout, and iteration based on real-world usage.

• Be a true partner to product, design, and operations by developing a deep understanding of the workflows and challenges faced by payroll operators and partners.

• Build internal and partner-facing tools that improve the visibility, reliability, and explainability of how money moves through the payroll system.

• Reduce friction in our systems by improving workflows, architecture, and tooling for both developers and operators.

• Role model clear, critical thinking through code, proposals, and diagrams that help teams align and move forward together.

• Raise the quality bar by working in the open, giving thoughtful feedback, mentoring teammates, and helping the team ship work we’re proud of.

Who You Are

• Experience with staff-level ownership and delivery of production systems end-to-end, from design through deployment and operation.

• Experience building internal tools, developer platforms, or product systems that support complex operational workflows.

• Ability to navigate ambiguous problem spaces and bring structure through thoughtful design and collaboration.

• Comfort debugging complex systems and investigating issues that span multiple services or infrastructure layers.

• Ability to articulate technical tradeoffs to engineers and cross-functional partners.

• While we don't have requirements for programming languages, experience with or, at minimum, a desire to learn our current stack is helpful: Python/Django, React, Typescript, AWS, Terraform, Postgres, Temporal, Github.

Engineering Culture at Check

At Check, engineering operates as one team. Engineers are staffed based on business priorities, not tied to fixed domains. Engineers stay close to the work and to each other’s decisions. The team is small and operates with a high level of ownership. Work does not sit waiting on ownership boundaries, and people step in to move things forward when something is stuck.

Travel & Office Policy

The Check team is distributed across the US. Roles can be remote, hybrid, or based in one of our offices in New York City or San Francisco. We offer ample opportunities and encourage employees to attend team offsites, events, and hackathons throughout year. All Checketeers gather in the spring for our annual 3-day company retreat.

For our in-office and hybrid employees, our offices are open all week. We provide meals on Tuesdays and Thursdays and there are regular happy hours, game nights, and other in-person events.

Remote work at Check requires the ability to perform all responsibilities without distraction or disruption, while maintaining quality, effective communication, and productivity.

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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.