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Territory Account Executive, Retail - Downers Grove, IL

Toast · Downers Grove, IL · Sales : Retail Sales AEs

Posted Sep 9, 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 time you sold something in a market where your company wasn't known yet.

What they are checking: Whether they can build trust and win deals without an established brand to lean on.

Tell me about a time you promised something to close a deal. How did you make sure it was delivered?

What they are checking: Whether they set honest expectations and partner with onboarding teams after the sale.

What does a founder's mindset mean to you in a sales role?

What they are checking: Whether they're comfortable with ambiguity and helping build processes, not just following them.

What would you do

How would you prospect convenience stores, grocery stores and bottle shops in the western Chicago suburbs?

What they are checking: Whether they have a practical, hands-on plan for building pipeline in a new vertical.

Walk me through how you'd run a discovery conversation with an independent liquor store owner.

What they are checking: Whether they ask about real pain points like inventory, age verification and checkout speed.

How do you run a demo that feels built for that customer rather than a generic walkthrough?

What they are checking: Whether they connect product features to the specific store's needs.

A store owner says they're happy with their current POS system. How do you respond?

What they are checking: Whether they can uncover hidden problems without pushing or criticizing the competitor.

How would you handle a long sales cycle with a small business owner who keeps delaying?

What they are checking: Whether they can stay persistent and find the real reason for delay.

About the work

How do you use Salesforce to manage your pipeline and forecast accurately?

What they are checking: Whether they keep their CRM clean and use it to plan, not just to report.

What do you know about the challenges grocery and convenience stores face with inventory and margins?

What they are checking: Whether they've done homework on the retail vertical, which differs from restaurants.

Practice this interview out loud.

Offer builds a real interview for this exact role at Toast from your resume and this job description, asks the questions one at a time, and tells you what landed. The first one is free.

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The full job description

As published by Toast.

After years of building an innovative POS platform for restaurateurs, Toast is expanding its offerings into other food and beverage concepts such as convenience stores, grocery stores, and bottle shops. This role will require a founder’s mindset as we grow Toast’s presence in this new vertical with a new offering: the Toast Retail platform.  As a Retail Account Executive, you will be part of a founding team that is transforming the way convenience stores, grocery stores, and bottle shops operate. Using a consultative approach, you will prospect, build relationships, and sign up new accounts. By understanding their unique needs, you will develop a customized solution that helps their business thrive. We need your passion, sales expertise, and entrepreneurial spirit to help us build the Toast brand in an assigned geographic territory. A day in the life (Responsibilities)  • Use a consultative approach to prospect, build relationships, and sign up new convenience stores, grocery stores and bottle shops • Generate lists of prospective convenience stores, grocery stores, and bottle shops and manage the entire sales cycle from initial call to close  • Conduct demos and develop a solution that best meets the prospect’s needs  • Partner with teams across the business to ensure that expectations set during the sales process are met in delivery  • Leverage Salesforce (our CRM) to manage all sales activities  • Understand the competitive landscape and determine how to best position Toast in the market What you’ll need to thrive (Requirements) • An entrepreneurial and feedback-driven mindset • Strong communication, organizational, and presentation skills with the ability to sell and negotiate at all decision-making levels • Proven track record of success in meeting and exceeding goals • Ability to work in a fast-paced, entrepreneurial and team environment • Self-motivated, creative, flexible, and willing to navigate ambiguity Lives in or in proximity to market and w illingness to travel 25% or more What will help you stand out (Nonessential Skills/Nice to Haves) • Retail operations experience 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 https://careers.toasttab.com/toast-benefits .   The estimated Total Targeted Cash compensation range for this role is listed below. Total Targeted Cash for this role includes base salary, commission, and bonus (if eligible). This role qualifies for uncapped commissions. The starting salary will be determined based on skills, experience, and geographic location. In addition to cash compensation, our total rewards components include benefits and equity (if eligible). You can learn more about how we align pay with local labor markets in our Geographic Pay Zone Philosophy . Total Targeted Cash $128,000 — $205,000 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:  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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