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Service Delivery Specialist

Check - Remote - Remote - posted 2026-08-12

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Check is an embedded payroll platform that enables payroll businesses to launch, grow, and scale. As a Service Delivery Specialist on the Operations team, you'll be a critical player in delivering exceptional service to Check's largest partners while protecting trust and scaling operations. You'll triage and resolve complex partner escalations spanning payroll, tax, compliance, and money movement. Working across Operations, Engineering, Product, and Support, you'll monitor partner Slack channels, respond with urgency and ownership, and serve as a trusted subject matter expert for high-touch service delivery. You'll dig into escalation trends to uncover root causes and recommend high-leverage improvements to product, process, and service delivery. Key responsibilities include: driving visibility and accountability by surfacing key themes, metrics, and risks to leadership; partnering cross-functionally to close loops on edge cases and streamline workflows; and owning internal and partner-facing documentation to ensure materials stay current and aligned with evolving processes and regulations. Ideal candidates bring 5+ years in operations, service delivery, or support roles with direct payroll and/or tax operations experience. B2B SaaS or Fintech background is valued. You're a strategic problem-solver equally comfortable rolling up your sleeves and stepping back to improve systems. You communicate effectively across technical and non-technical audiences, especially in ambiguous or high-pressure moments. You're passionate about improving systems at the root and delivering reliable service, and you're comfortable using structured data to identify trends and drive improvements. Familiarity with Slack, Claude Cowork, Notion, and Zendesk is a plus. Check is distributed across the US with offices in New York City and San Francisco. This role is fully remote, though the company encourages attendance at team offsites, events, and an annual 3-day spring company retreat.

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