Payroll Support Specialist

Summary

Join Check and help redefine payroll! As a Payroll Support Specialist, you will provide exceptional service to partners and their customers, leveraging your payroll and tax expertise to solve complex support issues. You will manage a high volume of support requests, ensuring accuracy and compliance while building strong relationships. This role requires strong communication, problem-solving skills, and the ability to collaborate across teams. Check offers a supportive and collaborative work environment with excellent benefits, including comprehensive health insurance, paid parental leave, flexible PTO, and a 401k plan. The ideal candidate will have 4+ years of client-facing experience and 2+ years in payroll, with a passion for solving customer problems. Check is a distributed team with offices in NYC and San Francisco, offering remote work options with occasional in-person events.

Requirements

• Have 4+ years in client or partner-facing role
• Have 2+ years of experience in payroll
• Have a deep passion for solving customer problems
• Thrive in high-volume, fast-paced environments—you’re organized, nimble, and decisive
• Have an eagle eye for details, especially when moving quickly
• Communicate clearly and kindly—over email, phone, or chat
• Comfort with ticketing systems and tracking work (ie Salesforce, ZenDesk, etc)
• Willingness and interest in attending our annual 3 day company offsite in the spring

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
• Solve hard problems. You’ll dive deep into payroll and tax questions, ensuring accuracy, compliance, and clarity every step of the way
• Be a source of calm and confidence. Whether it’s your 10th ticket of the day or your 110th, you’ll build trust by bringing empathy, ownership, and transparency to every interaction
• Know when to pick up the phone. 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 wisely. You’ll know when to loop in a teammate, when to escalate, and when to pick up the phone to solve something live
• Collaborate across teams. Whether you're triaging a bug to Engineering or assisting the Tax team at quarter-end, you’ll be a critical connector inside the company, facilitating communication and cooperation in all directions
• Deliver service that feels personal. Not just professional, but memorable—you're here to make people feel heard, helped, and valued

Benefits

• 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