The Work

At Check, we make paying and filing taxes simple, enabling our partners to build best-in-class payroll businesses. When payroll data is wrong, the impact rarely stays contained to one paycheck. Fixing those issues can require changes across multiple payrolls, quarters, tax jurisdictions, payments, and filings. Our Payroll Support team owns that work.

As Payroll Support Manager, you'll lead the people responsible for investigating and resolving these complex historical payroll issues. Your team brings deep payroll and tax expertise; your job is to create the environment and operating structure that allows them to apply it effectively.

This is first and foremost a people and operations leadership role. You'll own priorities, performance, capacity, escalation management, and the team's day-to-day operating rhythm. You'll work closely with a senior SME who will serve as your a technical counterpart, while you focus on making the team itself stronger, more predictable, and easier to scale.

You don't need to arrive as a payroll corrections expert. You do need to be comfortable leading highly specialized people, learning a complicated domain quickly, and knowing when to lean into the details versus when to bring in the right expert.

In this role, you will:

• Own the team's day-to-day operating rhythm, including priorities, queue health, resource allocation, standups, escalation paths, and SLA performance.
• Manage and develop a team of experienced payroll operations specialists through regular coaching, feedback, performance management, and career development.
• Create visibility into team performance and surface risks, bottlenecks, and emerging trends before they become larger problems.
• Partner with the team's senior SME to turn technical expertise into repeatable processes, documentation, and broader team capability.
• Own complex operational escalations and coordinate the right technical or cross-functional partners when deeper expertise is required.
• Partner closely with leaders across Support, Filing, Tax Operations, Product, and R&D on issues that cross functional boundaries.
• Serve as a thought partner to the head of the department on team strategy, staffing, performance, and operational decisions.

Tools for the Job

The ideal candidate will have:

• Startup or high-growth company background.
• 4-6+ years in operations, technical support, support operations, client service, or a similarly execution-heavy environment.
• Meaningful people management experience. You've directly managed a team, coached performance, and held clear standards for both outcomes and how the work gets done.
• Strong operational judgment. You can look at competing priorities, limited capacity, SLAs, customer impact, and risk and make a clear call on what should happen next.
• A track record of formal people management. You've hired, manage team growth, and understand how to organize people around team metrics.
• Strong communication skills. You can translate between team-level detail and leadership-level framing, and you know which audience needs which version.
• A genuine learner. You'll be getting fluent in a niche domain on the job, and you find that interesting rather than uncomfortable. Comfort managing people who may initially know more about the technical subject matter than you do.
• A bias toward building durable systems. When you see the same problem twice, your instinct is to improve the process rather than simply solve it again.

Nice to have

• Familiarity with payroll or payroll tax is a plus, but it is not required.
• Experience in fintech, payments, financial operations, or another regulated or technically complex domain.

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.