Payroll Support Specialist
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.
In this role, you will:
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.
Many backgrounds could fit this role, but ideal candidates will have most or all of the following:
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
Preference given to candidates in Mountain or Pacific time zones
Travel and Office Policy
The Check team is distributed across the US and we have offices in New York City and San Francisco. While we welcome remote work, we believe time together in person is valuable and important. We offer ample opportunities and encourage employees to attend team offsites, events, and hackathons throughout the year! We expect all team members to attend our annual 3-day company offsite each spring.
For our in-office and hybrid employees, our offices are open all week. We provide meals on Tuesdays and Thursdays and the team hosts regular happy hours, game nights, etc.
What we offer:
For full-time employees, 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.
The actual annual salary for this role depends on each candidate’s experience, qualifications and work location. Most new hires are placed near the midpoint of this range to ensure fairness with our existing team’s compensation:
The expected range in San Francisco, NYC, LA, and Seattle is between $77,000 and $87,000.
The expected range for all other locations is between $65,500 and $75,500.
About the job
Apply for this position
Payroll Support Specialist
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.
In this role, you will:
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.
Many backgrounds could fit this role, but ideal candidates will have most or all of the following:
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
Preference given to candidates in Mountain or Pacific time zones
Travel and Office Policy
The Check team is distributed across the US and we have offices in New York City and San Francisco. While we welcome remote work, we believe time together in person is valuable and important. We offer ample opportunities and encourage employees to attend team offsites, events, and hackathons throughout the year! We expect all team members to attend our annual 3-day company offsite each spring.
For our in-office and hybrid employees, our offices are open all week. We provide meals on Tuesdays and Thursdays and the team hosts regular happy hours, game nights, etc.
What we offer:
For full-time employees, 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.
The actual annual salary for this role depends on each candidate’s experience, qualifications and work location. Most new hires are placed near the midpoint of this range to ensure fairness with our existing team’s compensation:
The expected range in San Francisco, NYC, LA, and Seattle is between $77,000 and $87,000.
The expected range for all other locations is between $65,500 and $75,500.