On-site
SaaS
greenhouse
About this role
Toast creates technology to help restaurants and local businesses succeed in a digital world, helping business owners operate, increase sales, engage customers, and keep employees happy.
As a Flex Account Executive, you will be part of a team that is transforming the way restaurants operate. In this role, you will provide flexible sales coverage across designated territories, stepping in to support the business when Territory Account Executives are out on leave or taking extended holidays.Using a consultative approach, you will prospect, build relationships, and sign up new restaurateurs in each assigned territory. By understanding their unique needs, you will develop customized solutions that help their businesses thrive.
This role requires adaptability, a willingness to travel, and the ability to quickly establish relationships and build momentum in different markets. We need your passion and expertise to help us build the Toast brand and ensure consistent sales coverage across our territories.
This is a field sales opportunity based out of a personal home office with 25% travel required.
A day in the life (Responsibilities)
- Provide sales coverage across assigned territories during periods when Territory Account Executives are out on leave or extended holidays.
- Quickly onboard to new territories, understand local market dynamics, and build relationships with prospective restaurant owners.
- Generate list of prospective restaurants 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 <
Selling Motion
Prospecting
Channel / Partner
Sell through partners, resellers, or alliances
Buyer Persona
C-Suite
Selling to executive decision-makers
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 questionThis Account Executive position at Toast involves managing the full sales cycle from prospecting through close.
SaaS sales roles typically involve consultative selling with longer deal cycles.
The Canadian sales market is growing rapidly, with competitive compensation increasingly matching US benchmarks.
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