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.