Mid Market Account Executive, Toast 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, and this is one of the key sales roles that proves the commercial motion as we pursue increasingly complex retail accounts.
Role Overview
As a founding Mid Market Account Executive for Toast Retail, you will source and close multi-location retail deals 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 fully exist at Toast Retail yet. You will help build it, one deal at a time.
This is not a role for someone who wants to inherit a finished playbook. Some proof points exist from our SMB business, leadership is investing, and there is a set of open questions that closers in the field have to go answer. What does discovery look like when the buyer is a VP of Operations and not an owner? Which 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 hypotheses, test them in live deals, and feed what works back so the next AEs can run it.
You will report to the Manager, Mid Market Sales, Toast Retail. This is a remote opportunity with travel expectations of 30% or more, including store walks and on site visits.
A day in the life (Responsibilities)
- Pipeline and prospecting: Build a qualified pipeline of multi-location grocery, liquor, and convenience operators through category research, cold calling, networking, and close partnership with our SMB Retail teams to identify accounts ready to move upmarket.
- Retail centric discovery: Run disciplined discovery against buying committees rather than single owners. Learn the operational realities that move a category buyer, from inventory depth and scan data to shrink, margin, and compliance, and turn them into a compelling case for Toast Retail.
- Value based selling: Create demand by educating prospects on the Toast Retail value proposition through demonstrations and tailored business cases. Sell on platform value and outcomes over price, and help operators understand which products actually fit their scale.
- Full lifecycle ownership: Own the entire journey, from lead development and financial structuring to contract negotiation and close. Collaborate with Account Service and Implementation to ensure a seamless handoff on retail installs that are meaningfully harder than a single site.
- Complex deal navigation: Manage lengthy sales cycles with real ambiguity. Multithread across operations, finance, IT, and merchandising, and develop champions inside layered retail organizations.
- Internal collaboration: Partner with Legal, Deal Desk, Biz Ops, and Finance to structure deals, and hold your ground in negotiations so terms align with Toast's goals. Work with Product, Marketing, and Enablement to close the gaps between us and a repeatable Mid Market Retail motion, and escalate the ones you cannot close yourself.
- Build as you close: Convert what works in your live deals into discovery notes, demo flows, and business case models the next AEs can run. Distinguish a repeatable process from a one off hero deal, and help codify the former.
- Voice of the retailer: Bring the Mid Market retailer's needs back into the product roadmap with specificity and evidence, not anecdotes.
- Revenue mindset: Optimize for long term realized revenue, not just bookings. Evaluate the full financial impact of every deal, ask what it will actually cost us, and make thoughtful trade offs on pricing, discounts, and terms while protecting Toast's bottom line.
- Operational excellence: Maintain high standards of execution, prioritization, and follow through in Salesforce and the broader GTM tech stack, and help establish the conversion benchmarks that do not exist yet.
What you'll need to thrive (Requirements)
- 5+ years of successful technology or professional services sales experience, ideally within SaaS, payments, or retail or restaurant industry technology.
- A track record sourcing and closing complex, multi-stakeholder deals, ideally multi-location or upmarket.
- Proven skills in complex deal development, financial structuring, negotiation, and closing with both new and existing customers, with a focus on selling on value rather than deep discounting.
- Proficiency with MEDDPICC or a comparable qualification methodology, plus disciplined pipeline management and forecasting.
- A builder's instinct. You are energized rather than frustrated by ambiguity, and when a process is missing your instinct is to write it rather than wait for it.
- Exceptional customer engagement and active listening. You do not just pitch, you solve problems for operators.
- Strong written and verbal communication, including the ability to hold the room with executive stakeholders.
- Comfort educating customers on the fundamentals of US credit card processing, including surcharging and processing nuances.
- Strong organizational skills and a disciplined, process driven approach to selling, reporting, and tracking.
- Ability to travel 30% or more.
What will help you stand out
- 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 selling into franchised organizations, navigating both franchisor and franchisee requirements, buying processes, and stakeholder management
- Experience working with cross-functional stakeholders to complete complex RFPs, bonus if you’ve helped write a RFP for a prospect just starting their evaluation process
- Experience helping stand up a new segment, vertical, or motion inside an existing company, especially taking an SMB product upmarket.
- Experience in a fast paced, high growth technology environment.
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
The base salary range for this role is listed below. The starting salary will be determined based on skills, experience, and geographic location. In addition to base salary, our total rewards components include cash compensation (overtime, bonus/commissions if eligible), equity, and benefits. You can learn more about how we align pay with local labor markets in our Geographic Pay Zone Philosophy.
The estimated Total Targeted Cash compensation range for this role is listed below. Total Targeted Cash for this role includes base salary, commission, and bonus (if eligible). This role qualifies for uncapped commissions. The starting salary will be determined based on skills, experience, and geographic location. In addition to cash compensation, our total rewards components include benefits and equity (if eligible). You can learn more about how we align pay with local labor markets in our Geographic Pay Zone Philosophy.
How Toast Uses AI in its Hiring Process
Throughout the hiring process, our goal is to get to know you. We use AI tools to support our recruiters and interviewers with tasks like note-taking, summarization, and documentation of interviews to ensure they can be fully focused on your conversation. All hiring decisions are made by people. We ask that you complete interviews and assessments on your own, without real-time AI tools, recording, or transcription bots, unless we tell you otherwise in advance. To learn more:
Our Approach to Hybrid Working
We embrace a hybrid work model that fosters in-person collaboration while valuing individual needs. Our goal is to build a strong culture of connection as we work together to empower the hospitality community, regardless of location. Please visit the Locations page on our career site to learn more about our in-office expectations by region:
People Are the Secret Ingredient in Our Recipe for Success
At Toast, our employees are our secret ingredient—when they thrive, we thrive. The restaurant industry brings together people with a wide range of backgrounds, experiences, and perspectives, and we value that same breadth at Toast. We strive to build a culture grounded in authenticity, respect, and humility, where every Toaster has a real opportunity to grow, contribute, and do their best work—raising the bar in delivering exceptional experiences for our customers and each other.
Apply today!
Toast is committed to creating an accessible and inclusive hiring process. As part of this commitment, we strive to provide reasonable accommodations for persons with disabilities to enable them to access the hiring process. If you need an accommodation to access the job application or interview process, please contact candidateaccommodations@toasttab.com.
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