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 s
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Common Interview Questions And Answers

1. HOW DO YOU PLAN YOUR DAY?

This is what this question poses: When do you focus and start working seriously? What are the hours you work optimally? Are you a night owl? A morning bird? Remote teams can be made up of people working on different shifts and around the world, so you won't necessarily be stuck in the 9-5 schedule if it's not for you...

2. HOW DO YOU USE THE DIFFERENT COMMUNICATION TOOLS IN DIFFERENT SITUATIONS?

When you're working on a remote team, there's no way to chat in the hallway between meetings or catch up on the latest project during an office carpool. Therefore, virtual communication will be absolutely essential to get your work done...

3. WHAT IS "WORKING REMOTE" REALLY FOR YOU?

Many people want to work remotely because of the flexibility it allows. You can work anywhere and at any time of the day...

4. WHAT DO YOU NEED IN YOUR PHYSICAL WORKSPACE TO SUCCEED IN YOUR WORK?

With this question, companies are looking to see what equipment they may need to provide you with and to verify how aware you are of what remote working could mean for you physically and logistically...

5. HOW DO YOU PROCESS INFORMATION?

Several years ago, I was working in a team to plan a big event. My supervisor made us all work as a team before the big day. One of our activities has been to find out how each of us processes information...

6. HOW DO YOU MANAGE THE CALENDAR AND THE PROGRAM? WHICH APPLICATIONS / SYSTEM DO YOU USE?

Or you may receive even more specific questions, such as: What's on your calendar? Do you plan blocks of time to do certain types of work? Do you have an open calendar that everyone can see?...

7. HOW DO YOU ORGANIZE FILES, LINKS, AND TABS ON YOUR COMPUTER?

Just like your schedule, how you track files and other information is very important. After all, everything is digital!...

8. HOW TO PRIORITIZE WORK?

The day I watched Marie Forleo's film separating the important from the urgent, my life changed. Not all remote jobs start fast, but most of them are...

9. HOW DO YOU PREPARE FOR A MEETING AND PREPARE A MEETING? WHAT DO YOU SEE HAPPENING DURING THE MEETING?

Just as communication is essential when working remotely, so is organization. Because you won't have those opportunities in the elevator or a casual conversation in the lunchroom, you should take advantage of the little time you have in a video or phone conference...

10. HOW DO YOU USE TECHNOLOGY ON A DAILY BASIS, IN YOUR WORK AND FOR YOUR PLEASURE?

This is a great question because it shows your comfort level with technology, which is very important for a remote worker because you will be working with technology over time...

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