Staff Software Engineer

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.

The Work

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.

In this role, you will:

• 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.

Our Stack: 

• 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

Tools for the job:

• 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).

What we offer:

For full-time employees, Check offers company-sponsored medical, dental, vision, short-term/long-term disability, and basic life insurance coverage, effective on their first day of work. We also provide stock options, flexible PTO and sick leave, up to 16 weeks of fully paid parental leave for new parents, flexible return-to-work, 9 annual holidays, a 401k retirement plan, and a $100 monthly stipend for home internet and mobile phone expenses.

The actual annual salary for this role depends on each candidate’s experience, qualifications, and work location. Most new hires are placed near the midpoint of this range to ensure fairness with our existing team’s compensation. 

• 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.

We accept applications on an ongoing basis with no specified deadline.

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 a couple of times a year. All Checketeers gather in the spring for a required 3-day company offsite.

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.