Senior Payroll Support Specialist

Senior Payroll Support Specialist

Reports to: Support Manager

Compensation: Up to $85,000 per year based on experience

We’re looking for a Senior Payroll Support Specialist to join OnTheClock, a growing SaaS company focused on time tracking, scheduling, and embedded payroll for small and mid-sized businesses. In this role, you’ll be a trusted resource for customers and internal teams, supporting complex payroll and time tracking needs, including failed payrolls, quarterly and annual tax filings, and ongoing account health across phone, ticket, and chat channels.

At OnTheClock, we’re continuing to expand the tools we offer to help small businesses run better and pay their teams with confidence. Our long-term goal is to reach one million users, and payroll support plays a critical role in that mission. You’ll collaborate closely with Support, Product, Engineering, Customer Success, and Sales to provide high-touch, personalized support for more complex payroll customers, apply payroll and compliance knowledge to real-world scenarios, proactively identify risks, and surface insights that help improve our product, processes, and customer experience. You’ll do this in an environment that values trust, growth, and strong collaboration, supported by competitive pay, great benefits, and clear opportunities for career progression.

This is a hands-on, fast-paced role ideal for someone who enjoys problem-solving, clear communication, and taking ownership of customer outcomes. As OnTheClock grows, this role offers a defined career path with opportunities to deepen payroll and compliance expertise, expand influence across teams, and progress into more senior or specialized roles over time within a team that values development, accountability, and long-term success.

Key Responsibilities

• Support customers with in-depth payroll inquiries, failed payrolls, and time tracking issues, including quarterly and annual tax filings.
• Provide high-touch, personalized assistance to larger or more complex payroll customers following implementation, ensuring accuracy and confidence.
• Proactively monitor payroll accounts to ensure they are in good standing, resolve “needs attention” items, and prevent payroll failures.
• Provide timely, high-quality troubleshooting support across phone, ticket, and chat channels, meeting service-level expectations while resolving platform-related questions and issues.
• Manage individual case volume and workload to ensure balanced team contribution, accountability, and consistent support coverage.
• Participate in product training, releases, and beta testing; surface customer feedback, trends, and recurring issues to the Support Manager to support ongoing product and experience improvements.

Required Qualifications

• One plus year of customer service experience 
• Three plus years of experience working with a payroll solution within a support-facing role or equivalent
• Passion for problem-solving and helping support OnTheClock’s customer experience
• Excellent verbal and written communication skills
• Comfortable working with support tools (i.e., Live Chat, Salesforce, Ring Central) and providing clear and consistent ticket documentation
• Comfortable learning technical concepts and documenting steps to reproduce
• Ability to multitask 

Preferred Skills & Qualifications

• Experience with Salesforce or Zendesk (CRM) style ticketing systems
• Familiarity with SLA’s and obtaining solutions through knowledge-based articles and help libraries
• De-escalation skills, sales or retention exposure, and the ability to work with diverse people dynamics

You're wondering, what is OnTheClock?

OnTheClock, founded in 2004, is a Michigan-based SaaS (web-based) software company that provides real-time time tracking, scheduling, and payroll for businesses. Our web-based software and apps provide employers with a simple way to track employee hours, establish work schedules, and pay employees all in one system.  OnTheClock has a great culture, and we are looking for like-minded people who can deliver the best service possible to our customers.

What we look for in you

• Positive - whatever it takes attitude
• Analytical - drills down into data and loves technology, data, and spreadsheets
• Growth Mindset - curious and always learning
• Deep Expertise  - smarter than us at your craft. We want you to challenge yourself and us.
• Build Up Others - teach others as you work
• Results Focused - ability to achieve and prove results
• Culture Fit - Must fit in here at OTC, in line with our values - https://www.ontheclock.com/meetUs.aspx#our-values
• Be A Doer - always looking for new ways to look at data and make recommendations
• Find us on LinkedIn to understand more about us

Why Should You Work Here With Us

• 2023 - 2025 Crain’s Best Places to Work recipient

• Competitive pay
• Flextime
• Hybrid work environment
• 100% paid health insurance
• The kitchen is stocked with drinks and snacks
• Free company lunch every Thursday
• Paid time off
• 9 paid holidays
• $100k life insurance
• 401K matching retirement plan
• Short-term disability
• Long-term disability 
• Continuing education is encouraged with $1,000 per year
• Blue Cross dental and vision
• Career growth
• 4.9-star Glassdoor review
• 4.8-star product review

The finer print

• This position is eligible as a fully remote role for individuals 50 miles outside our Clinton Township, MI office.  Candidates who live within a 50-mile radius will be expected to follow the OTC hybrid work model.
• To be considered, applicants must reside outside the following U.S. states: California, New York, New Jersey, Washington, Colorado, Massachusetts, Oregon, and Hawaii.
• An I-9 form must be completed at hire to confirm work authorization.
• If you require reasonable accommodation to complete this application, contact amanda@ontheclock.com.