Mid-Market Sales Manager, 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.This role is the person who helps build the commercial motion as we shift towards increasingly complex upmarket accounts.

Role Overview

As Manager of Mid-Market Sales for Toast Retail, you will lead a small team of Mid-Market Account Executives pursuing multi-location retail 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 exist at Toast Retail yet. You will build it.

This is not a role for someone looking to inherit a playbook and run it well. There is no Mid-Market Toast Retail playbook. A growing set of proof points from our SMB business, a leadership team that is investing, and a set of open questions that someone has to go answer. What does discovery look like when the buyer is a VP of Operations and not an owner? Which of our 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 the hypotheses, run them in the field, and turn what works into something repeatable that the next ten AEs can execute.

Expect to spend real time outside your own team. Getting this motion off the ground means sitting with Product on inventory and scan data gaps, with Marketing on messaging that lands with a category buyer, with Enablement on training that does not exist yet, with Deal Desk and Finance on structures we have not offered before, and with Onboarding on i