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 implementations that are meaningfully harder than a single site install. Your ability to move those partners without formal authority over any of them will matter as much as your ability to coach a deal. This is a player coach role in year one. You will carry a number yourself while you hire and build the team, which means you will be closing Mid-Market Retail deals before you are coaching them. That is deliberate. The person who writes this playbook should draw from their own first-hand experiences from running the motion, not just observations of other people running it. As the team scales, your quota shifts to theirs. You will report to the VP of Sales, Toast Retail. This is a remote opportunity with travel expectations up to 40 percent of the time. A day in the life • Carry and deliver an individual quota in year one (player-coach) while you hire, onboard, and ramp your team, transitioning to a full team number as your team scales. • Hire, develop, motivate, and manage a quota achieving Mid-Market sales team from the ground up, setting the bar for talent in a brand new function • Build and codify the Mid-Market Retail sales process: discovery frameworks, demo flows, business case models, mutual action plans, and executive proposals tailored to grocery, liquor, and convenience buyers • Run a disciplined sales process and coach your team on qualification rigor, multithreading, and champion development inside complex retail organizations • Own live Mid-Market deals end to end yourself, then convert what you learn into discovery frameworks, demo flows, business cases, and proposals the team can run • Get in the field. Join discovery calls, sit in on site visits, and walk stores with your reps so the playbook you write is grounded in what actually happens in front of a customer • Own all stages of the sales lifecycle with your team: pipeline generation, executive meetings, value