Technical Support Expert, Enterprise

Customer Care Expert - Enterprise

Start Date: October 19th - Training is 8-10 weeks remote. There is no PTO allowed during training.

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.

A day in the life

The Toast Enterprise Support team delivers advanced, omnichannel technical support to our most complex enterprise clients — corporate restaurant brands, national franchises, and international locations. As an Enterprise Support Expert, you'll resolve highly complex, high-risk technical issues across a broad and varied product landscape, manage demanding enterprise stakeholders, and bring order to a fast-paced, ambiguous environment — all while fielding incoming questions across phone, chat, and email.

What you’ll do (Responsibilities)

  • Troubleshoot hardware, financial transaction mechanics, API integrations, and menu configuration issues across a wide range of Toast products for our Enterprise customers.
  • Diagnose and resolve issues at the intersection of Toast and third-party systems, including 3rd party ordering APIs and enterprise accounting integrations, following established troubleshooting paths and escalating when a case falls outside documented guidance.
  • Manage a steady mix of inbound case traffic across phone, chat, and email, keeping your active case backlog current and flagging aging cases to your lead or manager.
  • Help triage incoming workload based on account tier and urgency, following team guidelines on prioritization.
  • Communicate clearly across audiences — from front-of-house restaurant staff to corporate IT contacts — translating technical issues into actionable guidance.
  • Support de-escalation of difficult customer situations, bringing in your manager or a senior teammate on high-stakes, financially impacted, or executive-level cases.
  • Own customer issues through to resolution on moderately difficult cases, partnering with Customer Success, Engineering, Onboarding, and Product as needed and looping in your lead on cases with broader implications.
  • Share solutions in Slack and keep your own case notes and peer resources current; may act as an informal resource for newer or less experienced teammates.

What you’ll need to thrive (Requirements)

  • 2-4 years of experience in a Technical Support role responsible for customer satisfaction and championing the customer experience.
  • Ability to quickly learn Toast's product suite, with the ability to apply that knowledge across a wide range of technical issues.
  • Comfortable spotting less-obvious solutions to moderately difficult problems, and knowing when to escalate issues that fall outside established documentation or SOPs.
  • Solid foundational understanding of how software, hardware, and networks interact, with a track record of picking up new technical skills on the job.
  • Good communication and organizational skills, with the ability to flex between front-line restaurant staff and business stakeholders.
  • Experience managing multichannel (phone, chat, email) support.
  • Works well with general instruction on new or unfamiliar assignments, and normally needs little day-to-day direction on established work.

What will help you stand out (Nonessential Skills/Nice to Haves)

  • Business to business technical support.
  • Possess a high level of product knowledge of POS hardware: the function of different devices and how they operate in a restaurant environment.
  • Open to schedules that may include weekends, holidays and nights.

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.

Our Total Rewards Philosophy

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

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.

Zone A
$31.50—$31.50 USD
Zone B
$27.25—$27.25 USD
Zone C
$25—$25 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:

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:

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.

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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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Common Interview Questions And Answers

1. HOW DO YOU PLAN YOUR DAY?

This is what this question poses: When do you focus and start working seriously? What are the hours you work optimally? Are you a night owl? A morning bird? Remote teams can be made up of people working on different shifts and around the world, so you won't necessarily be stuck in the 9-5 schedule if it's not for you...

2. HOW DO YOU USE THE DIFFERENT COMMUNICATION TOOLS IN DIFFERENT SITUATIONS?

When you're working on a remote team, there's no way to chat in the hallway between meetings or catch up on the latest project during an office carpool. Therefore, virtual communication will be absolutely essential to get your work done...

3. WHAT IS "WORKING REMOTE" REALLY FOR YOU?

Many people want to work remotely because of the flexibility it allows. You can work anywhere and at any time of the day...

4. WHAT DO YOU NEED IN YOUR PHYSICAL WORKSPACE TO SUCCEED IN YOUR WORK?

With this question, companies are looking to see what equipment they may need to provide you with and to verify how aware you are of what remote working could mean for you physically and logistically...

5. HOW DO YOU PROCESS INFORMATION?

Several years ago, I was working in a team to plan a big event. My supervisor made us all work as a team before the big day. One of our activities has been to find out how each of us processes information...

6. HOW DO YOU MANAGE THE CALENDAR AND THE PROGRAM? WHICH APPLICATIONS / SYSTEM DO YOU USE?

Or you may receive even more specific questions, such as: What's on your calendar? Do you plan blocks of time to do certain types of work? Do you have an open calendar that everyone can see?...

7. HOW DO YOU ORGANIZE FILES, LINKS, AND TABS ON YOUR COMPUTER?

Just like your schedule, how you track files and other information is very important. After all, everything is digital!...

8. HOW TO PRIORITIZE WORK?

The day I watched Marie Forleo's film separating the important from the urgent, my life changed. Not all remote jobs start fast, but most of them are...

9. HOW DO YOU PREPARE FOR A MEETING AND PREPARE A MEETING? WHAT DO YOU SEE HAPPENING DURING THE MEETING?

Just as communication is essential when working remotely, so is organization. Because you won't have those opportunities in the elevator or a casual conversation in the lunchroom, you should take advantage of the little time you have in a video or phone conference...

10. HOW DO YOU USE TECHNOLOGY ON A DAILY BASIS, IN YOUR WORK AND FOR YOUR PLEASURE?

This is a great question because it shows your comfort level with technology, which is very important for a remote worker because you will be working with technology over time...

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