Remote Staff Engineering Lead

Building at Check

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.

Our Team

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.

The work

In the Staff Engineering Lead role, you are responsible for turning complex, high-impact problems into solutions that work in production.

The systems you work on handle money movement, tax calculations, and filings at scale. Check has already paid over one million people through our platform (), and the work here is about making those systems more reliable, more explainable, and easier to operate as we grow.

Some of the core challenges the engineering team is solving:

• Scaling systems that power payroll calculations, tax payments, and filings as volume and complexity increase

• Designing systems that move and reconcile money across parties, while making results clear and traceable for partners

• Supporting partners as they migrate large employer bases onto Check, where the work spans collaborative system design, product decisions, and scaling infrastructure

• Using AI to automate complex operational workflows, such as tax notice triage and reducing manual employer setup work

You are expected to take on the most important problems in the business as they emerge and drive them to a working outcome. Your decisions directly shape how these systems behave in production and how our partners build their payroll businesses on top of them.

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

You will directly manage a small group of engineers who are working across different areas of the business. Your role is to bring strong judgment to what we build and how we build it, and to set a high bar for ownership, accountability, and growth across the engineers you manage.

You should identify where you can have the most impact, communicate your focus clearly, and take action without waiting for direction.

This is a team that works with urgency on hard problems together. People jump into Slack huddles to work through thorny investigations, and we close out each week by sharing appreciation for each other’s work.

In this role, you will:

• Take on complex, high-impact problems and drive them to resolution

• Develop engineers into stronger owners across changing areas of the business

• Step into the work when needed: designing a new system, managing a project, or fixing a bug

• Work directly with product and operations, including defining product behavior, clarifying requirements, and working support tickets when needed

• Improve systems and developer workflows over time

• Use AI tools to increase speed, improve the quality of what we ship, and raise the bar for how the team builds

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 CI/CD

What we look for

• Experience owning and delivering production systems end-to-end

• Experience leading and developing engineers into stronger owners

• Comfort switching between coaching and doing based on need

• A track record of driving outcomes in ambiguous environments

• Strong technical judgment and ability to simplify systems

• Willingness to step into messy or operational problems

• Excitement about how AI is changing how teams build

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.

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

Travel and Office Policy

This role can be remote, hybrid, or based in one of our offices in New York City or San Francisco. The Check team is distributed across the US! While we welcome remote work, personal time is valuable and important. We offer ample opportunities and encourage employees to attend team offsites, events, and hackathons a couple of times a year! All employees must be willing to attend our annual 3-day company offsite in the 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.

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

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.