Software Engineer, Staff

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.

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.

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