Mid Market Retail Account Executive

This is a fully remote position, open to applicants in United States.

📋 Description

• Identify and finalize multi-location retail agreements with a focus on grocery, liquor, and convenience store operators.

• Develop a robust pipeline via category analysis, cold outreach, networking, and collaboration with SMB Retail teams.

• Engage in discovery sessions with buying committees and convert operational requirements into persuasive Toast Retail proposals.

• Provide education to potential clients through product demonstrations and customized business cases.

• Take charge of lead generation, financial setup, contract discussions, and deal closure.

• Work in conjunction with Account Service and Implementation teams for seamless retail-install transitions.

• Navigate lengthy sales cycles and engage multiple stakeholders across operations, finance, IT, and merchandising.

• Collaborate with Legal, Deal Desk, Biz Ops, Finance, Product, Marketing, and Enablement teams.

• Transform successful deal strategies into discovery documentation, demo sequences, and business case frameworks.

• Integrate retailer requirements into the product development roadmap.

• Focus on achieving long-term revenue growth while safeguarding Toast’s financial interests.

• Uphold high execution standards and set conversion metrics in Salesforce and the wider GTM technology ecosystem.

⛳️ Requirements

• A minimum of 5 years of successful sales experience in technology or professional services, preferably in SaaS, payments, or retail/restaurant tech.

• Proven ability to source and finalize complex, multi-stakeholder agreements, ideally in multi-location or upmarket settings.

• Expertise in developing complex deals, financial structuring, negotiation, and closing.

• Familiarity with MEDDPICC or similar qualification frameworks.

• Strong skills in pipeline management and sales forecasting.

• Outstanding customer engagement capabilities combined with active listening skills.

• Excellent written and verbal communication skills, particularly in engaging executive stakeholders.

• Comfortable educating clients on US credit card processing, including surcharging and processing intricacies.

• Strong organizational abilities and a process-oriented approach to sales, reporting, and tracking.

• Willingness to travel 30% of the time or more.

• Experience in grocery, convenience, liquor, or specialty retail is a plus.

• Understanding of retail operations, encompassing inventory depth, SKU management, scan data, shrinkage, category management, age verification, compliance, fuel, and foodservice is advantageous.

• Background with franchised organizations is beneficial.

• Experience in completing complex RFPs is a plus.

• Familiarity with launching new segments, verticals, or sales initiatives would be advantageous.

• Experience in a fast-paced, high-growth technology setting is a plus.

🏝️ Benefits

• Competitive salary and benefits offerings.

• Cash compensation including overtime, bonuses, or commissions if applicable.

• Uncapped commission potential.

• Eligibility for equity options.

• Flexible work arrangements available.

• Access to AI tools across various disciplines.

• Reasonable accommodations provided for individuals with disabilities.