Retail Sales District Manager- Toronto, Canada

Retail Sales District Manager – Toronto, Canada at Toast . 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, and bottle shops. 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 have spent the past two years studying this expansion opportunity and building an all‑in‑one SaaS platform designed to meet the specific needs of retail customers. We are looking for a Founding 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 the first field leader 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 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. Remote opportunity with up to 35% travel. Candidates must live local to Toronto or be willing to relocate. Responsibilities Build a GTM motion for Toast retail in a new market Help build the foundations for our internal processes in international markets Partner and collaborate with peers and parallel teams across the business to ensure that expectations set during the sales process are met in delivery (enablement, onboarding, product) Strategically utilize Salesforce (our CRM) and other technology to drive productivity, report on forecast deal pipelines, and analyze conversion rates Possess strong leadership skills with the ability to act decisively, develop systems to measure progress, monitor risks and identify changes needed Promote trust and encourage collaboration to effectively resolve conflict and navigate change management Provide guidance into the sales motion in Canada including but not limited to organizational structure and lead sources Drive new business growth across your assigned district 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 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 Nice to Have 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 Bread puns encouraged but not required The estimated Total Targeted Cash compensation range for this role is $196,000—$314,000 CAD. Total Targeted Cash for this role consists of a base salary, commission, benefits, and equity (if eligible). This role qualifies for uncapped commissions. The starting salary will be determined based on skills, experience, and geographic location. Diversity, Equity, and Inclusion is baked into our recipe for success. At Toast, our employees are our secret ingredient—when they thrive, we thrive. We embrace diversity with authenticity, inclusivity, respect, and humility. By embedding these principles into our culture and design we create equitable opportunities for all. We thrive together. 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 restaurant community. Toast is committed to creating an accessible and inclusive hiring process. If you need an accommodation to access the job application or interview process, please contact 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. #J-18808-Ljbffr