Check

Provide partner support by investigating payroll and tax issues and collaborating with internal teams to resolve bugs and improve workflows. | Requires 4+ years client-facing experience and 2+ years in payroll, HR tech, or fintech with strong investigative and communication skills. | About Check Payroll is broken. Come fix it alongside a team that’s as passionate as you are! At Check, 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. 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 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 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. -- 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.

As a Service Delivery Specialist, you will triage and resolve complex partner escalations across payroll, tax, compliance, and money movement. You will also monitor partner communications and drive visibility and accountability by surfacing key themes and metrics to leadership. | Candidates should have 5+ years of experience in operations, service delivery, or customer success, ideally in fintech or payroll. Strong communication skills and a passion for improving systems are essential. | Building at Check 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. Our Team Payroll is broken. Come fix it alongside a team that’s as passionate as you are! At Check, you'll use creative problem-solving, critical thinking, and grit to impact every business we build. We view problems to solve and jobs to be done as opportunities to contribute to the solution; we ignore conventional role boundaries in favor of the unique strengths and value each builder brings to our team and to our mission. Join us if you’re ready to roll up your sleeves and redefine payroll. Let’s simplify the complex, make a real impact, and create a better future for businesses of every size. The Work Our Operations team is scaling fast to meet the growing needs of our partners and product. As a Service Delivery Specialist, you'll be essential to how we run at the problem, protect partner trust, and deliver exceptional service at scale. You’ll work across Operations, Engineering, Product, and Support to stabilize high-impact workflows, resolve complex issues across payroll, tax, compliance, and money movement, and shape how we deliver service as we grow. If you're energized by solving messy problems, thinking big while working small, and turning complexity into clarity, this is your role. In this role, you will: 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 partner Slack channels and respond with urgency, ownership, and a bias for clarity and resolution. Step in to directly support early-stage (quickstart) partners, enabling the broader team to stay focused on our highest-impact relationships. 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 by surfacing key themes, metrics, and risks to leadership, turning signals from the field into actionable priorities that reduce partner friction and improve how we operate. Partner cross-functionally with Ops, Product, and Engineering to close loops on edge cases, streamline workflows, and simplify for scale. Take ownership of internal and partner-facing documentation, ensuring materials stay up to date, easy to follow, and aligned with evolving processes and regulations. Tools for the job Many backgrounds could fit this role, but ideal candidates will have some or all of the following: 5+ years in operations, service delivery, customer success, or support, ideally in fintech, compliance, or payroll. Direct experience with tax, compliance, or payroll operations, especially in partner-facing or high-volume environments. Proven ability to operate with urgency and ownership in high-complexity, fast-moving environments. Strategic problem-solver who’s equally comfortable rolling up their sleeves and stepping back to improve the system. Strong communicator across technical and non-technical audiences, especially in ambiguous or high-pressure moments. Passion for improving systems at the root and delivering high-quality, reliable service. Experience using structured data to identify trends and drive improvements. Familiarity with tools like Slack, ChatGPT, Notion, and Zendesk. We build best when we come together on level ground. 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 embrace remote work, we believe time together in person is where we do our best work. We offer ample opportunities and encourage employees to attend team offsites, events, and hackathons a couple of times a year! We expect all employees to attend our annual 3-day company retreat in the fall. 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, 16 weeks of fully paid parental leave for all 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 location of work. 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 $180,000 and $198,000. The expected range for all other locations is between $153,000 and $168,300. We accept applications on an ongoing basis with no specified deadline. 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, consistent with applicable federal, state and local law. 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.

As a Service Delivery Specialist, you will triage and resolve complex partner escalations across payroll, tax, compliance, and money movement. You will also monitor partner communications and drive visibility and accountability by surfacing key themes and metrics to leadership. | Candidates should have 5+ years of experience in operations, service delivery, or customer success, ideally in fintech or payroll. Strong communication skills and a passion for improving systems are essential. | Building at Check 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. Our Team Payroll is broken. Come fix it alongside a team that’s as passionate as you are! At Check, you'll use creative problem-solving, critical thinking, and grit to impact every business we build. We view problems to solve and jobs to be done as opportunities to contribute to the solution; we ignore conventional role boundaries in favor of the unique strengths and value each builder brings to our team and to our mission. Join us if you’re ready to roll up your sleeves and redefine payroll. Let’s simplify the complex, make a real impact, and create a better future for businesses of every size. The Work Our Operations team is scaling fast to meet the growing needs of our partners and product. As a Service Delivery Specialist, you'll be essential to how we run at the problem, protect partner trust, and deliver exceptional service at scale. You’ll work across Operations, Engineering, Product, and Support to stabilize high-impact workflows, resolve complex issues across payroll, tax, compliance, and money movement, and shape how we deliver service as we grow. If you're energized by solving messy problems, thinking big while working small, and turning complexity into clarity, this is your role. In this role, you will: 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 partner Slack channels and respond with urgency, ownership, and a bias for clarity and resolution. Step in to directly support early-stage (quickstart) partners, enabling the broader team to stay focused on our highest-impact relationships. 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 by surfacing key themes, metrics, and risks to leadership, turning signals from the field into actionable priorities that reduce partner friction and improve how we operate. Partner cross-functionally with Ops, Product, and Engineering to close loops on edge cases, streamline workflows, and simplify for scale. Take ownership of internal and partner-facing documentation, ensuring materials stay up to date, easy to follow, and aligned with evolving processes and regulations. Tools for the job Many backgrounds could fit this role, but ideal candidates will have some or all of the following: 5+ years in operations, service delivery, customer success, or support, ideally in fintech, compliance, or payroll. Direct experience with tax, compliance, or payroll operations, especially in partner-facing or high-volume environments. Proven ability to operate with urgency and ownership in high-complexity, fast-moving environments. Strategic problem-solver who’s equally comfortable rolling up their sleeves and stepping back to improve the system. Strong communicator across technical and non-technical audiences, especially in ambiguous or high-pressure moments. Passion for improving systems at the root and delivering high-quality, reliable service. Experience using structured data to identify trends and drive improvements. Familiarity with tools like Slack, ChatGPT, Notion, and Zendesk. We build best when we come together on level ground. 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 embrace remote work, we believe time together in person is where we do our best work. We offer ample opportunities and encourage employees to attend team offsites, events, and hackathons a couple of times a year! We expect all employees to attend our annual 3-day company retreat in the fall. 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, 16 weeks of fully paid parental leave for all 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 location of work. 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 $180,000 and $198,000. The expected range for all other locations is between $153,000 and $168,300. We accept applications on an ongoing basis with no specified deadline. 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, consistent with applicable federal, state and local law. 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.