Payroll Support Specialist

Check • San Francisco, CA

15d • $65,500 - $87,000 • Remote

About The Position

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 out the full story | Tune in.
Check is far more than just API infrastructure. We’re a springboard for building and scaling payroll businesses.
The Support team keeps payroll running smoothly 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, our team investigates what happened, explains it clearly, and drives toward a solution.
This role sits at the intersection of payroll expertise and technical product knowledge, and the work is fast-moving and highly investigative. A typical day involves deconstructing complex payroll scenarios, digging into root cause analysis, partnering with internal teams to identify solutions, and communicating with partners whose experience with payroll may range from “seasoned professional” to “just getting started”. You’ll develop deep expertise in Check’s platform and the broader payroll ecosystem while building trusted, long-term relationships with the partner teams you support.
Support also sits at the center of the company. The team works closely with Engineering, Product, Tax, and Risk to troubleshoot issues, surface product insights, and improve the platform. If you enjoy solving layered, high-impact problems, translating technical concepts into clear and actionable explanations, and seeing the direct impact of your work on partners, this role may be for you. Being part of the Support team offers a rare window into how payroll infrastructure operates at scale. It rewards people who enjoy focused problem-solving, have strong attention to detail, and find satisfaction in untangling complex operational puzzles, while becoming a trusted partner to the teams they work with every day.

Requirements

• 4+ years in client or partner-facing role, supporting technical products
• 2+ years working at a payroll provider or platform, with a strong understanding of payroll workflows, tax concepts, and compliance fundamentals
• Experience working in high-volume support or operations environments where the right balance of speed and precision really matters
• Strong investigative instincts and a deep sense of ownership over ambiguous problems
• An eagle eye for detail, maintaining accuracy even when moving quickly
• Comfort collaborating across technical, operational, and administrative teams to solve partner problems and enable new business capabilities
• Clear and kind communication style across email, chat, and phone
• Fluency with ticketing and case management systems, preferably ZenDesk
• Willingness and availability to attend our annual 3 day company offsite each spring

Nice To Haves

• Preference given to candidates in Mountain or Pacific time zones

Responsibilities

• Keep the queue flowing. You’ll tackle a high number of support requests (mostly via email-like tickets) with speed and precision, always meeting or exceeding SLAs.
• Investigate complex payroll problems. You’ll dive deep into payroll and tax questions, breaking the issues down and tracing root causes through our systems to ensure ongoing accuracy, compliance, and clarity every step of the way.
• Collaborate across the company to resolve issues. You’ll be a critical connector within Check, partnering across Engineering, Product, Tax, and Risk to troubleshoot problems, escalate bugs, and drive solutions that unblock partners quickly.
• Surface patterns and improve the system. Your work will be critical in identifying recurring partner questions and operational friction points, and surfacing insights that help us improve our documentation, workflows, and product behaviors.
• Be a source of calm and confidence. 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.
• Jump on a call when it moves things forward. Most of our work is done through written communication, but some problems need a human voice. You’ll build rapport and resolve complex issues in real time when it matters most.
• Escalate thoughtfully. You’ll exercise careful judgment about how and when to pull others in on a problem or escalate upward, and you’ll ensure everyone has clear context so they can quickly understand the problem and help identify a path to 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.

Benefits

• Check offers company-sponsored medical, dental, vision, short-term/long-term disability, and basic life insurance coverage, effective on their first day of work.
• We also provide stock options, flexible PTO and sick leave, up to 16 weeks of fully paid parental leave for new parents, flexible return-to-work, 9 annual holidays, a 401k retirement plan, and a $100 monthly stipend for home internet and mobile phone expenses.

What This Job Offers

• Job Type: Full-time
• Career Level: Mid Level
• Education Level: No Education Listed