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 proposition development, deal structuring, negotiation, and close
• Partner across Product, Marketing, Enablement, Deal Desk, Finance, and Onboarding to close the gaps that stand between us and a repeatable Mid-Market motion, and escalate the ones you cannot close yourself
• Bring the voice of the Mid-Market retailer back into the product roadmap with specificity and evidence, not anecdotes
• Forecast accurately in a business with little historical data, and be honest about what you know versus what you are still learning
• Assess and engage in competitive RFPs
• Leverage GTM tech stack to run an efficient, AI-anchored motion: establish the conversion benchmarks that do not exist yet, and report on them credibly.
• Distinguish repeatable process from one off hero deals, and build only the former into the playbook
• Stay close to the competitive landscape across grocery, liquor, and convenience technology, and position Toast Retail sharply against incumbents

What you'll need to thrive

• 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
• Fluency in the operational realities of retail: inventory depth and SKU management, scan data, shrink, category management, age verification and compliance, fuel and foodservice
• Experience in a fast paced, high growth technology environment
• A proven track record of creating a winning culture that performs at a high level

Is this your kind of build?

The best version of this hire is someone who reads a role with this much white space and gets excited rather than nervous, and who wants to close the first ten deals themselves before handing the playbook to a team. If you want to point at a Mid-Market business two years from now and say you built it, we would like to talk.

AI at Toast

At Toast, one of our company values is that we're hungry to build and learn. We believe learning new AI tools empowers us to build for our customers faster, more independently, and with higher quality. We provide these tools across all disciplines, from Engineering and Product to Sales and Support, and are inspired by how our Toasters are already driving real value with them. The people who thrive here are those who embrace changes that let us build more for our customers; it’s a core part of our culture.

Our Total Rewards Philosophy
We strive to provide competitive compensation and benefits programs that help to attract, retain, and motivate the best and brightest people in our industry. Our total rewards package goes beyond great earnings potential and provides the means to a healthy lifestyle with the flexibility to meet Toasters’ changing needs. Learn more about our benefits at https://careers.toasttab.com/toast-benefits.