Job Description: Building at Check

Company Overview

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 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.

Position Overview: Service Delivery Specialist

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.

Responsibilities

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.
• Step in to directly support early-stage (quickstart) partners, enabling the broader team to stay focused on our highest-impact relationships.
• 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.

Qualifications

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

• 5+ years in operations, service delivery, customer success, or support, ideally in fintech, compliance, or payroll.
• Direct experience with tax, compliance, or payroll operations, especially in partner-facing or high-volume environments.
• 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, ChatGPT, Notion, and Zendesk.

Travel and Office Policy

The Check team is distributed across the US, and we have offices in New York City and San Francisco. While we embrace remote work, we believe time...