On-site
SaaS
greenhouse
About this role
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
Selling Motion
Prospecting
Outbound-Heavy
Self-sourced pipeline via cold outreach
Buyer Persona
C-Suite
Selling to executive decision-makers
Territory
Geographic
Region-based territory assignment
Requirements at a Glance
Typical Day — Account Executive
Estimates based on role type and selling motion — actual may vary by company.
SaaS — Interview Intel
Typical Sales Cycle
30–90 days (SMB) · 3–9 months (Mid-Market) · 6–18 months (Enterprise)
Common Buyer Objections
- "We're locked into a contract with [competitor]"
- "We built something in-house already"
- "We don't have budget until next quarter"
- "Our team won't adopt another tool"
Key Industry Metrics
Hot Topics to Reference
- • AI-native product disruption
- • PLG vs sales-led motion debate
- • Vertical SaaS consolidation
- • Usage-based pricing models
Use these insights to speak the buyer's language in interviews.
Tags
Walk me through your discovery process.
Template questionHow do you handle a prospect who goes silent mid-deal?
Template questionTell me about your largest closed deal and the sales cycle.
Template questionHow do you build business cases for stakeholders?
Template questionDescribe a deal you lost and what you learned.
Template questionAs an Account Executive with Toast, you'll own the entire revenue pipeline and be measured on quota attainment.
Expect to work with recurring revenue models where customer retention is as important as acquisition.
The Canadian sales market is growing rapidly, with competitive compensation increasingly matching US benchmarks.
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