Mid Market Retail 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.

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