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 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).
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. 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
Diversity, Equity, and Inclusion is Baked into our Recipe for Success
At Toast, our employees are our secret ingredient—when they thrive, we thrive. The restaurant industry is one of the most diverse, and we embrace that diversity with authenticity, inclusivity, respect, and humility. By embedding these principles into our culture and design, we create equitable opportunities for all and raise the bar in delivering exceptional experiences.
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. To learn more about how we work globally and regionally, check out: https://careers.toasttab.com/locations-toast.
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 [email protected].
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Skills Required
- 5+ years of sales experience in a sourcing and/or closing role
- 3+ years of leadership experience
- Proven track record of success meeting/exceeding sales targets
- Experience using Salesforce CRM
- Must live local to Toronto or be willing to relocate
- Ability to inspire, motivate, and develop a sales team
- Entrepreneurial, self-motivated, creative, and able to perform under pressure
- Management experience building customer-facing, quota-achieving full cycle sales teams
- Experience working in a tech environment
- Experience in a fast-paced, high-growth environment
- Experience working in a retail environment
- Proven track record of creating a high-performing sales culture
What the Team is Saying
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Toast Compensation & Benefits Highlights
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Parental & Family Support — Paid parental leave and family‑forming resources are highlighted as generous and inclusive. Backup child/adult care and caregiving supports further strengthen this area.
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Leave & Time Off Breadth — Flexible PTO, paid company holidays, and a paid sabbatical after extended tenure indicate broad time‑off options. Feedback suggests these policies compare well with peer tech employers.
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Wellbeing & Lifestyle Benefits — Access to no‑cost therapy/coaching, wellness stipends, and financial‑wellness resources is emphasized. These offerings extend support beyond core insurance into day‑to‑day wellbeing.
Toast Insights
What We Do
Toast is the all-in-one platform built for restaurants of all sizes. Toast provides a single platform of software as a service (SaaS) products and financial technology solutions that give restaurants everything they need to run their business, including point of sale, payments, supplier management, digital ordering and delivery, marketing and loyalty, and team management. By serving as the restaurant operating system across dine-in, takeout, and delivery channels, Toast helps restaurants increase revenue, streamline operations and deliver amazing guest experiences.
Why Work With Us
Our recipe for an awesome workplace: One splash of friendship A dollop of impact A sprinkle of no hierarchy & A heavy spoonful of individuality Mix these ingredients in a fast-paced and hardworking environment. Best paired with a side of interesting people who always bring their whole selves to work. *100% Sunday scary free
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Toast Teams
Toast Offices
Hybrid Workspace
Employees engage in a combination of remote and on-site work.
