Staff Software Engineer

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.

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.

At Check, you’ll combine strong engineering fundamentals with a drive to build software that meaningfully improves how payroll businesses operate. Our platform powers the movement of money, tax calculations, and compliance workflows for thousands of businesses, and much of the work we do involves turning complex infrastructure into clear, reliable systems for operators and partners.

Our engineering team builds using cloud-native tools managed through infrastructure-as-code. We run a Python modular monolith that applies the principles of distributed systems while preserving the simplicity and ownership benefits of a mono-repo. Our systems rely on traditional HTTP APIs and durable asynchronous workflows to orchestrate everything from moving money to filing taxes.

As an engineer at Check, you’ll work closely with product, design, and operations teams to build tools and systems that help people run payroll reliably and confidently.

• 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.

• Python / Django for our API
• React and TypeScript for our frontends
• AWS and Terraform for our cloud infrastructure
• Postgres for our database
• Temporal for workflow orchestration
• GitHub for issue tracking and CI/CD

• 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.
• Strong communication skills and the ability to clearly explain technical tradeoffs to engineers and non-engineers alike.
• Proficiency in Python or Go (experience with Django, React, or TypeScript is a plus).

Building Together on Common Ground. The Check team is distributed across the US, and we have offices in New York City and San Francisco. While we embrace remote work, time together in person is where we do our best work. We offer ample opportunities and encourage employees to attend team offsites, events, and hackathons a couple of times a year! We expect all employees to attend our annual 3-day company retreat each 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, etc.