Payroll Support Specialist

Summary

Join Check's Support team and redefine payroll by providing exceptional service to partners and their customers. You will handle a high volume of support requests, solve complex payroll and tax issues, and build strong relationships. This role requires deep payroll and tax knowledge, excellent communication skills, and the ability to thrive in a fast-paced environment. You will collaborate with various teams within Check to ensure seamless service delivery. Check offers a comprehensive benefits package including health insurance, paid parental leave, flexible PTO, and more. The ideal candidate will have 4+ years in a client-facing role and 2+ years of payroll experience.

Requirements

• Have 4+ years in client or partner-facing role
• Have 2+ years of experience in payroll
• Are located in or willing to work Pacific Time Zone hours (8:30 AM – 5:30 PM PT)
• 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. Tackle a high number of support requests (mostly via email-like tickets) with speed and precision, always meeting or exceeding SLAs
• Solve hard problems. 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, 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—build rapport and resolve complex issues in real time when it matters most
• Escalate wisely. 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, 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

Preferred Qualifications

Willingness and interest in attending our annual 3 day company offsite in the spring

Benefits

• Company-sponsored medical, dental, vision, short-term/long-term disability, and basic life insurance coverage
• 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
• A $100 monthly stipend for home internet and mobile phone expenses