Retail Account Executive (Calgary, AB)

After years building the best POS platform for restaurateurs, Toast is expanding its offerings into other food and beverage concepts such as convenience stores, grocery stores,bottle shops and other retail customers. This role will require a founder’s mindset as we grow Toast’s presence in a new vertical with a new offering: the Toast Retail platform. Toast Retail is our newest vertical and our next big bet, and Canada will be a flagship international market for this expansion. We are looking for a Founding Account Executive to spearhead our Canadian Retail launch. 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. We’re looking for a passionate, entrepreneurial leader to launch and grow the Toast brand in this expanding market. You will own and execute a high-activity outside sales strategy, spending the majority of your time in the field engaging decision-makers directly at their places of business across Calgary and surrounding region. 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 • Willingness to travel 25% or more Lives in or in proximity to market 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. This role is for a current vacancy. 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). Total Targeted Cash $131,000—$210,000 CAD 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 candidateaccomm