Upmarket Retail Account Executive - Multi-Location

Toast; United States; Remote; USD 90,000 - 150,000; Full time

Job summary

Toast is expanding its Retail team and seeks a founding Mid Market Account Executive to source and close multi-location grocery, liquor, and convenience deals. You will build a new sales motion, navigate complex buying committees, and own the end-to-end process from discovery to close.

This remote role requires 30%+ travel including store walks and on-site visits. You will partner with Legal, Deal Desk, Biz Ops, and Finance to structure wins and collaborate with Product, Marketing, and

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 escalated the ones you cannot close yourself.
• Build as you close: Convert what works in your live deals

Job description

Toast is expanding its Retail team and seeks a founding Mid Market Account Executive to source and close multi-location grocery, liquor, and convenience deals. You will build a new sales motion, navigate complex buying committees, and own the end-to-end process from discovery to close.

This remote role requires 30%+ travel including store walks and on-site visits. You will partner with Legal, Deal Desk, Biz Ops, and Finance to structure wins and collaborate with Product, Marketing, and