Mid Market Account Executive, Toast Retail

The role

You will source and close multi-location retail deals for grocery, liquor, and convenience operators. You will help build the sales motion for the Toast Retail platform by testing hypotheses in live deals and feeding results back to the company.

What you will do

• Build a qualified pipeline of multi-location grocery, liquor, and convenience operators.
• Run disciplined discovery against buying committees.
• Create demand through demonstrations and tailored business cases.
• Own the entire journey from lead development to contract negotiation and close.
• Manage lengthy sales cycles and multithread across operations, finance, IT, and merchandising.
• Partner with Legal, Deal Desk, Biz Ops, and Finance to structure deals.
• Work with Product, Marketing, and Enablement to build a repeatable Mid Market Retail motion.
• Convert successful live deal elements into discovery notes, demo flows, and business case models.
• Bring Mid Market retailer needs back into the product roadmap.
• Maintain execution and tracking in Salesforce and the GTM tech stack.

Required qualifications

• 5+ years of successful technology or professional services sales experience, ideally within SaaS, payments, or retail or restaurant industry technology.
• Track record sourcing and closing complex, multi-stakeholder deals, ideally multi-location or upmarket.
• Proven skills in complex deal development, financial structuring, negotiation, and closing.
• Proficiency with MEDDPICC or a comparable qualification methodology.
• Disciplined pipeline management and forecasting.
• A builder's instinct for ambiguity.
• Exceptional customer engagement and active listening.
• Strong written and verbal communication.
• Ability to hold the room with executive stakeholders.
• Comfort educating customers on the fundamentals of US credit card processing.
• Strong organizational skills and a disciplined, process driven approach.
• Ability to travel 30% or more.

Nice to have

• Experience selling into or operating within grocery, convenience, liquor, or specialty retail.
• Fluency in the operational realities of retail: inventory depth, SKU management, scan data, shrink, category management, age verification, compliance, fuel and foodservice.
• Experience selling into franchised organizations.
• Experience working with cross-functional stakeholders to complete complex RFPs.
• Experience helping stand up a new segment, vertical, or motion inside an existing company.
• Experience in a fast paced, high growth technology environment.

Benefits

• Cash compensation (overtime, bonus/commissions if eligible)
• Equity (if eligible)
• Benefits

About the company

Toast is expanding its innovative POS platform into new food and beverage concepts like convenience stores, grocery stores, and bottle shops. The company is moving upmarket to pursue increasingly complex retail accounts.