Jobs › Toast

Associate Shipping Representative

Toast · Chicago, IL · Services : Team Suite Operations : Team

Posted Sep 18, 2026 · We last checked this listing on Oct 6, 2026

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Likely interview questions for this role

Written from this job description, not a generic list. Each one notes what the interviewer is really checking.

About your past

Tell me about a job where attention to detail really mattered. How did you avoid mistakes?

What they are checking: Whether they have proven habits for accuracy in repetitive, high-stakes work.

Tell me about a time you worked independently under a tight deadline.

What they are checking: Whether they can stay focused and accurate in a fast-paced role without someone checking in.

What would you do

These packages hold live payroll checks for our clients' employees. How do you make sure every one goes to the right address?

What they are checking: Whether they treat each package as someone's paycheck and build checks to prevent misdirected mail.

You notice a printed check is smudged or misaligned. What do you do?

What they are checking: Whether they stop and fix quality problems instead of shipping something a bank might reject.

A carrier misses a pickup on a payroll deadline day. How do you handle it?

What they are checking: Whether they act fast with vendors and alert Customer Care and Payroll Ops so clients aren't surprised.

The check sealing machine jams in the middle of a big run. What do you do?

What they are checking: Whether they can troubleshoot equipment calmly and protect the security of the checks while doing it.

About the work

Walk me through how you'd audit a package before it ships.

What they are checking: Whether they have a step-by-step check against client specifications instead of eyeballing it.

Why would shipment records and receipts matter for SOC 1 requirements?

What they are checking: Whether they understand that auditors rely on complete records proving payroll was handled properly.

How do you keep track of the weekly payroll schedule so no deadline sneaks up on the team?

What they are checking: Whether they plan ahead and communicate deadlines rather than reacting at the last minute.

How would you handle sensitive documents like checks and W-2s to keep them secure?

What they are checking: Whether they understand that these documents contain personal data and money and must be protected.

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The full job description

As published by Toast.

Toast creates technology to help restaurants and local businesses succeed in a digital world, helping business owners operate, increase sales, engage customers, and keep employees happy. The Shipping Representative is an important part of our Employee cloud team and critical to ensure timely and accurate payment to our clients employees. This role is responsible for printing, sealing, and shipping all live payroll checks to the customer address on file. This role requires the ability to work independently in a fast paced environment as well and an attention to detail. The role will require some internal communication between teams such as Customer care and Payroll Ops teams. A day in the life (Responsibilities)&nbsp; • &nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;Responsible for packaging and delivery of all payroll packages • &nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;Maintain client package specifications • &nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;Interact directly with shipping vendors to ensure materials are shipped timely and efficiently • &nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;Responsible for monitoring weekly payroll schedule and alerting staff of upcoming deadlines • &nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;Ensures quality control of printed checks and W-2s • &nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;Maintain shipment records and receipts for SOC-1 requirements • &nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;Maintains inventory for Payroll Operations team • &nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;Maintain printing and sealing equipment • &nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;Ensures all packages are audited prior to shipping &nbsp; What will help you stand out (Nonessential Skills/Nice to Haves) The individual that will excel in this position will have 2-3 years of experience in a similar high volume, high accuracy shipping logistics role with UPS/FedEx shipping software experience. Individuals with a college degree preferred. This position requires a flexible work schedule with the ability to work until 8 pm or later a few times a week. AI at Toast At Toast, one of our company values is that we're hungry to build and learn. We believe learning new AI tools empowers us to build for our customers faster, more independently, and with higher quality. We provide these tools across all disciplines, from Engineering and Product to Sales and Support, and are inspired by how our Toasters are already driving real value with them. The people who thrive here are those who embrace changes that let us build more for our customers; it’s a core part of our culture. &nbsp; Our Total Rewards Philosophy&nbsp; We strive to provide competitive compensation and benefits programs that help to attract, retain, and motivate the best and brightest people in our industry. Our total rewards package goes beyond great earnings potential and provides the means to a healthy lifestyle with the flexibility to meet Toasters’ changing needs. Learn more about our benefits at&nbsp;<a class="c-link" href="https://careers.toasttab.com/toast-benefits" target="_blank" data-stringify-link="https://careers.toasttab.com/toast-benefits" data-sk="tooltip_parent">https://careers.toasttab.com/toast-benefits . The starting pay rate for this role is below. Please note that there is no range for this role; the rate listed below is the only rate. You can learn more about how we align pay with local labor markets in our Geographic Pay Zone Philosophy . Pay Rate $18.27 &mdash; $29.33 USD How Toast Uses AI in its Hiring Process Throughout the hiring process, our goal is to get to know you. We use AI tools to support our recruiters and interviewers with tasks like note-taking, summarization, and documentation of interviews to ensure they can be fully focused on your conversation. All hiring decisions are made by people. We ask that you complete interviews and assessments on your own, without real-time AI tools, recording, or transcription bots, unless we tell you otherwise in advance. To learn more: https://careers.toasttab.com/ai-in-hiring Our Approach to Hybrid Working We embrace a hybrid work model that fosters in-person collaboration while valuing individual needs. Our goal is to build a strong culture of connection as we work together to empower the hospitality community, regardless of location. Please visit the Locations page on our career site to learn more about our in-office expectations by region:&nbsp; https://careers.toasttab.com/locations-toast People Are the Secret Ingredient in Our Recipe for Success At Toast, our employees are our secret ingredient—when they thrive, we thrive. The restaurant industry brings together people with a wide range of backgrounds, experiences, and perspectives, and we value that same breadth at Toast. We strive to build a culture grounded in authenticity, respect, and humility, where every Toaster has a real opportunity to grow, contribute, and do their best work—raising the bar in delivering exceptional experiences for our customers and each other. Apply today! Toast is committed to creating an accessible and inclusive hiring process. As part of this commitment, we strive to provide reasonable accommodations for persons with disabilities to enable them to access the hiring process. If you need an accommodation to access the job application or interview process, please contact candidateaccommodations@toasttab.com . ------ For roles in the United States, it is unlawful in Massachusetts to require or administer a lie detector test as a condition of employment or continued employment. An employer who violates this law shall be subject to criminal penalties and civil liability.

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