Mid Market Retail Account Executive

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

📋 Description

• Identify and secure multi-location retail agreements targeting grocery, liquor, and convenience operators.

• Develop a strong pipeline by conducting category research, cold outreach, networking, and collaborating with the SMB Retail teams.

• Conduct discovery sessions with buying committees and translate operational requirements into Toast Retail business propositions.

• Showcase the value proposition of Toast Retail and emphasize platform benefits and results.

• Manage lead generation, financial structuring, contract negotiations, and closing processes.

• Work in partnership with Account Service and Implementation teams during retail-install transitions.

• Navigate extended sales cycles and engage with multiple departments, including 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 processes, and business case frameworks.

• Offer data-driven feedback from retailers to inform the product roadmap.

• Maximize achieved revenue while safeguarding Toast’s profitability through pricing strategies, discounts, and terms.

• Uphold execution standards and set conversion benchmarks within Salesforce and the wider GTM tech ecosystem.

⛳️ Requirements

• Over 5 years of proven success in technology or professional services sales, preferably within SaaS, payments, or the retail/restaurant technology sectors.

• Demonstrated success in sourcing and finalizing complex, multi-stakeholder deals, ideally in multi-location or upmarket environments.

• Expertise in developing complex deals, financial structuring, negotiation, and closing with both new and existing clients.

• Familiarity with MEDDPICC or a similar qualification framework.

• Strong discipline in pipeline management and forecasting.

• Excellent customer engagement skills and active listening abilities.

• Proficient in both written and verbal communication, particularly in engaging with executive stakeholders.

• Capacity to educate customers on US credit card processing, including surcharging and related nuances.

• Strong organizational skills and a systematic approach to selling, reporting, and tracking.

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

🏝️ Benefits

• Competitive salary and benefits packages.

• Cash compensation that may include bonuses/commissions if eligible.

• Uncapped commission potential.

• Equity opportunities if eligible.

• Benefits that promote a healthy lifestyle.

• Flexibility to adapt to changing needs.

• Access to AI tools across various disciplines.

• Reasonable accommodations available for individuals with disabilities.