Mid Market Account Executive, Toast Retail

After years of building an innovative POS platform for restaurateurs, Toast is expanding into new food and beverage concepts: convenience stores, grocery stores, and bottle shops. The Toast Retail platform is already winning with independent operators. Now we are moving upmarket, and this is one of the key sales roles that proves the commercial motion as we pursue increasingly complex retail accounts. Role Overview As a founding Mid Market Account Executive for Toast Retail, you will source and close multi-location retail deals with a focus on grocery, liquor, and convenience operators. These are complex accounts with real buying committees, layered compliance requirements, deep inventory and SKU demands, and incumbent systems that took years to entrench. Winning them requires a sales motion that does not fully exist at Toast Retail yet. You will help build it, one deal at a time. This is not a role for someone who wants to inherit a finished playbook. Some proof points exist from our SMB business, leadership is investing, and there is a set of open questions that closers in the field have to go answer. What does discovery look like when the buyer is a VP of Operations and not an owner? Which SMB motions translate upmarket and which have to be rebuilt? What do we need from Product to be credible in a 40 store grocery chain? You will form hypotheses, test them in live deals, and feed what works back so the next AEs can run it. You will report to the Manager, Mid Market Sales, Toast Retail. This is a remote opportunity with travel expectations of 30% or more, including store walks and on site visits. A day in the life (Responsibilities) • Pipeline and prospecting: Build a qualified pipeline of multi-location grocery, liquor, and convenience operators through category research, cold calling, networking, and close partnership with our SMB Retail teams to identify accounts ready to move upmarket. • Retail centric discovery: Run disciplined discovery against buying committees rather than single owners. Learn the operational realities that move a category buyer, from inventory depth and scan data to shrink, margin, and compliance, and turn them into a compelling case for Toast Retail. • Value based selling: Create demand by educating prospects on the Toast Retail value proposition through demonstrations and tailored business cases. Sell on platform value and outcomes over price, and help operators understand which products actually fit their scale. • Full lifecycle ownership: Own the entire journey, from lead development and financial structuring to contract negotiation and close. Collaborate with Account Service and Implementation to ensure a seamless handoff on retail installs that are meaningfully harder than a single site. • Complex deal navigation: Manage lengthy sales cycles with real ambiguity. Multithread across operations, finance, IT, and merchandising, and develop champions inside layered retail organizations. • Internal collaboration: Partner with Legal, Deal Desk, Biz Ops, and Finance to structure deals, and hold your ground in negotiations so terms align with Toast's goals. Work with Product, Marketing, and Enablement to close the gaps between us and a repeatable Mid Market Retail motion, and escalate the ones you cannot close yourself. • Build as you close: Convert what works in your live deals into discovery notes, demo flows, and business case models the next AEs can run. Distinguish a repeatable process from a one off hero deal, and help codify the former. • Voice of the retailer: Bring the Mid Market retailer's needs back into the product roadmap with specificity and evidence, not anecdotes. • Revenue mindset: Optimize for long term realized revenue, not just bookings. Evaluate the full financial impact of every deal, ask what it will actually cost us, and make thoughtful trade offs on pricing, discounts, and terms while protecting Toast's bottom line. • Operational excellence: Maintain high standards of execution, prioritization, and follow through in Salesforce and the broader GTM tech stack, and help establish the conversion benchmarks that do not exist yet. What you'll need to thrive (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. You are energized rather than frustrated by ambiguity, and when a process is missing your instinct is to write it rather than wait for it. • Exceptional customer engagement and active listening. You do not just pitch, you solve problems for operators. • Strong written and verbal communication, including the ability to hold the room with 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. What will help you stand out • 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 RF