23 Check Technical Support Specialist Jobs Hiring Near You

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 Support team plays a critical role in keeping payroll running for thousands of businesses and millions of workers by supporting the platforms that build payroll products on top of Check's infrastructure. When questions arise or something doesn't behave as expected, we investigate what happened, explain it clearly, and drive toward a solution.

This role sits at the intersection of payroll expertise and technical product knowledge, and the work is fast-moving, analytical, and highly investigative. A typical day involves untangling complex payroll scenarios, identifying root causes, partnering across the company to solve problems, and communicating clearly with partners whose payroll expertise may range from seasoned professionals to first-time operators. Along the way, you'll develop deep expertise in Check's platform, payroll operations, and the broader payroll ecosystem while building trusted relationships with the partner teams you support.

Support sits at the center of Check's product ecosystem. We work closely with Engineering, Product, Tax, Risk, and other teams to troubleshoot issues, surface product insights, and improve the platform. Few roles offer the same visibility into how modern payroll infrastructure operates at scale. If you enjoy solving layered problems, asking thoughtful questions, and translating technical concepts into clear, actionable guidance, you'll thrive here.

In this role, you will:

• Provide exceptional partner support. You'll manage a high volume of partner requests, primarily through written communication. You'll balance urgency and responsiveness with thoughtful and thorough investigation, while independently driving complex issues toward resolution and consistently meeting or exceeding SLAs.

• Investigate complex payroll problems. You'll independently own some of our most complex payroll and tax issues, breaking problems into manageable pieces, tracing root causes across systems, and driving issues toward resolution with accuracy, curiosity, and ownership.

• Collaborate across the company to resolve issues. You'll partner closely with Engineering, Product, Tax, Risk, and other teams to troubleshoot issues, escalate bugs, and help drive solutions that unblock partners quickly.

• Surface patterns and improve the system. You'll proactively identify recurring partner questions, operational friction points, and product trends, surfacing insights that improve documentation, workflows, and product behavior. You'll also create and maintain documentation and operational resources that help the full team work more efficiently.

• Build trusted relationships. Whether you're working with experienced payroll professionals or teams who are brand new to the industry, you'll build trust by bringing empathy, ownership, and transparency to every interaction and explaining technical or operational issues in ways they understand.

• Support Check's Enterprise partners. You'll own relationships with some of Check's largest and most strategic partners, serving as a trusted resource through complex payroll scenarios, escalations, and ongoing operational support. You'll build a deep understanding of their business and proactively help drive successful outcomes.

• Escalate thoughtfully. You'll exercise strong judgment about how and when to engage cross-functional stakeholders, ensuring they have the context needed to quickly understand complex problems and drive efficient resolution.

• Deliver service that feels personal. You'll build lasting relationships with our partners by developing a deep understanding of their platforms and the businesses they serve. You'll establish yourself as a reliable and trusted resource by making people feel heard, helped, and valued.

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

• 4+ years in a client- or partner-facing role, supporting customers, partners, or technical products.

• 2+ years working at a payroll provider, payroll platform, HR technology company, fintech company, or in a role that required applying payroll knowledge to solve customer problems

• Experience balancing multiple priorities in a fast-paced support or operations environment

• Strong investigative instincts and genuine curiosity to understand not just what happened, but why

• Exceptional attention to detail and the ability to maintain accuracy while solving complex problems

• Comfortable collaborating across technical, operational, and administrative teams to solve partner problems and enable new business capabilities

• Excellent written communication skills with the ability to explain complex technical or operational concepts clearly and empathetically

• Experience using ticketing or case management systems (Zendesk preferred)

• Experience creating or improving internal documentation, SOPs, or operational processes

• Experience supporting enterprise, strategic, or high-value customer accounts preferred

• Willingness and availability to attend our annual 3 day company offsite each spring

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 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.

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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.