Toast Manager of Mid-Market Sales for Toast Retail leading a team to build a new sales motion targeting multi-location retail accounts. Responsible for hiring, coaching, and closing deals in complex retail environments.
Responsibilities
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.
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 proposition development, deal structuring, negotiation, and close
Qualification
A closer who is also a builderA genuine founder's mindsetExceptional cross functional influenceStrong written and verbal communicationWhat will help you stand outExperience standing up a new segment
Required
5+ years of sales experience in a sourcing and closing role, with a track record in Mid-Market or complex, multi stakeholder deals
3+ years of sales leadership experience with a proven record of building and developing quota achieving teams and excellence in outbound pipeline generation
Demonstrated expertise in complex deal development, financial structuring, negotiation, and closing with new and existing customers
Proficiency with MEDDPICC or a comparable qualification methodology, plus disciplined pipeline management and forecasting
A closer who is also a builder. You are recently and personally credible in front of a Mid-Market buyer, and you are not looking for a role where you stop selling
A genuine founder's mindset. You are energized rather than frustrated by ambiguity, and your instinct when a process is missing is to write it rather than ask for it
Exceptional cross functional influence. You have a history of getting Product, Marketing, and Operations partners to move on your priorities without owning them
Strong written and verbal communication, including the ability to hold the room with executive stakeholders and negotiate complex pricing arrangements
Comfortable educating customers and team members on the fundamentals of US credit card processing
What will help you stand out
Experience standing up a new segment, vertical, or motion inside an existing company, especially taking an SMB product upmarket
Experience selling into or operating within grocery, convenience, liquor, or specialty retail
