Software Engineer - Senior

About Check

Payroll is broken. It's still running on decades-old infrastructure. We're rebuilding it.

We don't run payroll ourselves — we power the businesses that do. As the inventors of embedded payroll, we're redefining how people get paid and making it easier for those businesses to launch, grow, and thrive.

On our team, you'll use creative problem-solving, critical thinking, and grit to simplify the complexity of payroll for thousands of employers of every size, across all industries. We ignore conventional role boundaries in favor of the unique strengths and values each builder brings to our mission: make paying people simple. Check out our origin story!

Check is far more than just API infrastructure. We’re a springboard for building and scaling payroll businesses. See how it works for our partners.

Engineering Culture at Check

Engineering at Check works as one small team with a lot of ownership. We staff engineers on business priorities rather than fixed domains, and when something is stuck, people step in to move it forward instead of waiting on ownership boundaries. AI is central to how we build, and very little of our code is written by hand. That makes engineering judgment more important: deciding on the right problems to solve, defining what "done" means, and working with AI to get there. A merged PR isn't the finish line. The work is done when it has had the intended outcomes.

About this role

As a senior engineer, you'll use technical depth, product sense and AI tools to solve hard problems on the platform that moves money, calculates taxes and runs compliance for thousands of businesses. You'll turn complex infrastructure into reliable systems that let our partners run payroll confidently and help thousands of people get paid.

What You'll Do

• Own problems from start to finish, from defining the problem and the impact you're aiming for through rollout and follow-through

• Use AI to research, prototype and build quickly, and own the quality of everything you ship, however it was written

• Set the bar for how your team builds with AI, including review standards, workflows and where human judgment can't be skipped

• Simplify your domain by spotting patterns, reducing complexity and questioning the status quo

• Make clear, well-reasoned decisions and write down the thinking behind them

• Raise your team's quality bar through reviews, candid feedback and mentorship

• Work across teams to understand partner and operator problems from the people who have them

What We're Looking For

• Senior-level experience building complex systems, ideally at scale or in a regulated industry

• Deep, hands-on experience building with AI tools, with clear opinions on where they help, where they fall short, and when to override them

• The ability to work autonomously on team-wide projects that have real business impact

• A track record of fast, sound decisions grounded in experience

• The curiosity and persistence to debug complex problems in intricate systems

• Comfort working cross-functionally with internal teams and partners

We don't require any particular programming language. You'll pick up our stack (Python/Django, React, TypeScript, AWS, Terraform, Postgres, Temporal, GitHub) as you go.

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.

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.