Service Delivery Specialist

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.

The Role

Our Operations team is scaling fast to meet the growing needs of our partners and product. As a Service Delivery Specialist, you'll be essential to how we run at the problem, protect partner trust, and deliver exceptional service at scale.

You'll work across Operations, Engineering, Product, and Support to stabilize high-impact workflows, resolve complex issues across payroll, tax, compliance, and money movement, and shape how we deliver service as we grow.

If you're energized by solving messy problems, thinking big while working small, and turning complexity into clarity, this is your role.

In This Role, You Will:

• Jump in quickly to triage and resolve complex partner escalations across payroll, tax, compliance, and money movement, bringing clarity to ambiguity and acting as a trusted subject matter expert.

• Monitor partner Slack channels and respond with urgency, ownership, and a bias for clarity and resolution.

• Deliver high-touch service to a concentrated portfolio of Check's largest partners.

• Dig into trends across escalations to uncover root causes, connect the dots, and recommend high-leverage improvements across product, process, and service delivery.

• Drive visibility and accountability by surfacing key themes, metrics, and risks to leadership, turning signals from the field into actionable priorities that reduce partner friction and improve how we operate.

• Partner cross-functionally with Ops, Product, and Engineering to close loops on edge cases, streamline workflows, and simplify for scale.

• Take ownership of internal and partner-facing documentation, ensuring materials stay up to date, easy to follow, and aligned with evolving processes and regulations.

Tools For The Job

Many backgrounds could fit this role, but ideal candidates will have some or all of the following:

• 5+ years in operations, service delivery, support or closely related role, including direct experience with payroll and/or tax operations.

• Experience in a B2B SaaS or Fintech organization.

• Proven ability to operate with urgency and ownership in high-complexity, fast-moving environments.

• Strategic problem-solver who's equally comfortable rolling up their sleeves and stepping back to improve the system.

• Strong communicator across technical and non-technical audiences, especially in ambiguous or high-pressure moments.

• Passion for improving systems at the root and delivering high-quality, reliable service.

• Experience using structured data to identify trends and drive improvements.

• Familiarity with tools like Slack, Claude Cowork, Notion, and Zendesk.

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 the 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.

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.