Retail Sales District Manager

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. We are looking for a District Manager to spearhead our Canadian Retail launch – starting by personally selling, shaping the GTM motion, and then building a sales team. Toast offers an all-in-one platform that helps restaurateurs and retailers operate their business, increase sales, engage guests, and keep employees happy. As a Founding District Manager, you will be one of the first sales leaders of our Canadian Retail Sales team and pivotal to the growth of the Toast brand in Canada. Reporting to the Regional Vice President of Retail Sales, you will help launch our Canadian presence, drive early wins, and then help build and scale the sales team. You’ll work closely with enablement, onboarding, and product teams to understand Retail operators’ unique needs and build solutions that help Retailers thrive. We’re looking for a passionate, entrepreneurial leader to launch and grow the Toast brand in this new market. You will be managing and supporting field based account executives. Candidates must live local to Toronto or be willing to relocate. A day in the life (Responsibilities) Hire, develop, motivate, and manage a quota-achieving sales team Coach your team on a full cycle sales process. This includes coaching on how to conduct efficient discovery meetings, live demos, and craft a solution proposal that best meets the prospective customer’s needs Spend time coaching and empowering your team through field visits that include walk-ins, prospecting, trade shows, and local business partnerships to help exceed quotas Partner and collaborate with peers and parallel teams across the business to ensure that expectations set during the sales process are met in delivery Strategically utilize Salesforce (our CRM) and other technology to drive productivity, report on forecast deal pipelines, and analyze conversion rates Accountable for the new business growth across your assigned district What you’ll need to thrive (Requirements) 5+ years of sales experience in a sourcing and/or closing role 3+ years of leadership experience Proven track record of success Passionate with the ability to inspire and motivate those around them Entrepreneurial, self-motivated, creative, and flexible with the ability to perform well under pressure What will help you stand out (Nonessential Skills/Nice to Haves) Management experience building customer-facing, quota-achieving full cycle sales teams Experience working in a tech environment Experience working in a fast-paced, high growth environment Experience working in a retail environment Proven track record of creating a winning culture that performs at a high level 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 lis…