Mid Market Retail Account Executive, Toast Retail

Toast

43d•$169,000 - $347,000•Remote

About The Position

Toast is expanding its innovative POS platform into new food and beverage concepts, including convenience stores, grocery stores, and bottle shops. The Toast Retail platform is seeking founding Mid Market Account Executives to source and close multi-location retail deals. This role is crucial for proving the commercial motion as Toast pursues increasingly complex retail accounts. The position involves building a new sales motion, as current playbooks are not fully established for these larger, more complex deals. The successful candidate will help define discovery processes for buyers like VPs of Operations, determine which SMB sales motions translate to upmarket, and identify product needs for larger chains. This is a remote opportunity with significant travel expectations.

Requirements

5+ years of successful technology or professional services sales experience, ideally within SaaS, payments, or retail or restaurant industry technology.
A 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 with both new and existing customers, with a focus on selling on value rather than deep discounting.
Proficiency with MEDDPICC or a comparable qualification methodology, plus disciplined pipeline management and forecasting.
A builder's instinct: energized by ambiguity and proactive in creating processes.
Exceptional customer engagement and active listening skills; ability to solve problems for operators.
Strong written and verbal communication, including the ability to engage executive stakeholders.
Comfort educating customers on the fundamentals of US credit card processing, including surcharging and processing nuances.
Strong organizational skills and a disciplined, process-driven approach to selling, reporting, and tracking.
Ability to travel 30% or more.

Nice To Haves

Experience selling into or operating within grocery, convenience, liquor, or specialty retail.
Fluency in the operational realities of retail: inventory depth and SKU management, scan data, shrink, category management, age verification and compliance, fuel and foodservice.
Experience selling into franchised organizations, navigating both franchisor and franchisee requirements, buying processes, and stakeholder management.
Experience working with cross-functional stakeholders to complete complex RFPs, bonus if you’ve helped write a RFP for a prospect just starting their evaluation process.
Experience helping stand up a new segment, vertical, or motion inside an existing company, especially taking an SMB product upmarket.
Experience in a fast-paced, high-growth technology environment.

Responsibilities

Build a qualified pipeline of multi-location grocery, liquor, and convenience operators through category research, cold calling, networking, and partnership with SMB Retail teams.
Run disciplined discovery against buying committees, understanding operational realities like inventory depth, scan data, shrink, margin, and compliance to build a compelling case for Toast Retail.
Create demand by educating prospects on the Toast Retail value proposition through demonstrations and tailored business cases, selling on platform value and outcomes.
Own the entire sales journey from lead development and financial structuring to contract negotiation and close, collaborating with Account Service and Implementation for seamless handoffs.
Manage lengthy sales cycles with ambiguity, multithreading across operations, finance, IT, and merchandising, and developing champions within retail organizations.
Partner with Legal, Deal Desk, Biz Ops, and Finance to structure deals and negotiate terms aligned with Toast's goals.
Work with Product, Marketing, and Enablement to close gaps and establish a repeatable Mid Market Retail sales motion.
Convert successful deal strategies into repeatable processes, discovery notes, demo flows, and business case models for future AEs.
Bring Mid Market retailer needs back into the product roadmap with specificity and evidence.
Optimize for long-term realized revenue, evaluating the full financial impact of deals and making thoughtful trade-offs on pricing and terms.
Maintain high standards of execution, prioritization, and follow-through in Salesforce and the GTM tech stack, and help establish conversion benchmarks.