Job Description: Building at Check

Position Overview

At Check, we make paying people simple. We are redefining how people get paid and making it easier for payroll businesses to launch, grow, and thrive. Check is more than just API infrastructure; it's a springboard for building and scaling payroll businesses.

Our Team

Payroll is broken, and we're looking for passionate individuals to help fix it. At Check, you'll utilize creative problem-solving, critical thinking, and grit to impact every business we build. We view problems and jobs to be done as opportunities to contribute, ignoring conventional role boundaries in favor of unique strengths and contributions. Join us if you're ready to redefine payroll, simplify complexity, make a real impact, and create a better future for businesses of all sizes.

The Work

Our Operations team is scaling rapidly to meet the growing needs of our partners and product. As a Service Delivery Specialist, you will be essential to our operations, protecting partner trust, and delivering exceptional service at scale. You will collaborate across Operations, Engineering, Product, and Support to stabilize high-impact workflows, resolve complex issues across payroll, tax, compliance, and money movement, and shape our service delivery as we grow. This role is ideal for individuals energized by solving complex problems, thinking big while working small, and turning complexity into clarity.

Key Responsibilities:

• Triage and Resolve Escalations: 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 and Respond: Monitor partner Slack channels and respond with urgency, ownership, and a bias for clarity and resolution.
• Support Early-Stage Partners: Directly support early-stage (quickstart) partners to enable the broader team to focus on high-impact relationships.
• Identify Root Causes: 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: Surface key themes, metrics, and risks to leadership, turning signals from the field into actionable priorities that reduce partner friction and improve operations.
• Cross-Functional Partnership: Partner with Ops, Product, and Engineering to close loops on edge cases, streamline workflows, and simplify for scale.
• Documentation Ownership: Take ownership of internal and partner-facing documentation, ensuring materials are up-to-date, easy to follow, and aligned with evolving processes and regulations.

Requirements

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

• Experience: 5+ years in operations, service delivery, customer success, or support, ideally in fintech, compliance, or payroll.
• Domain Expertise: Direct experience with tax, compliance, or payroll operations, especially in partner-facing or high-volume environments.
• Operational Agility: Proven ability to operate with urgency and ownership in high-complexity, fast-moving environments.
• Problem-Solving Skills: Strategic problem-solver who is equally comfortable rolling up their sleeves and stepping back to improve the system.
• Communication: Strong communicator across technical and non-technical audiences, especially in ambiguous or high-pressure moments.
• Systems Improvement: Passion for improving systems at the root and delivering high-quality, reliable service.
• Data Analysis: Experience using structured data to identify trends and drive improvements.
• Tool Familiarity: Familiarity with tools like Slack, ChatGPT, Notion, and Zendesk.

Company Culture

We build best when we come together on level ground.

Travel and Office Policy

The Check team is distributed across the US, with offices in New York City and San Francisco. While we embrace remote work, we believe in the value of in-person collaboration.