T

Toast

Builds restaurant and retail software and payments

Mid Market Account Executive

Account ExecutiveConfirmed live in the last 24 hours
Full-timeRemote in USA

About the Job

Requirements

  • At least 5 years of successful technology or professional services sales experience, ideally within SaaS, payments, or retail or restaurant industry technology.
  • A track record of 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, with the ability to work through ambiguity and create missing processes.
  • Customer engagement and active listening skills to solve problems for operators.
  • Strong written and verbal communication, including the ability to engage executive stakeholders.
  • Comfort educating customers on the fundamentals of U.S. 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.

Responsibilities

  • Build a qualified pipeline of multi-location grocery, liquor, and convenience operators through category research, cold calling, networking, and close partnership with SMB Retail teams to identify accounts ready to move upmarket.
  • Run disciplined discovery with buying committees and learn the operational factors affecting category buyers, including inventory depth, scan data, shrink, margin, and compliance, and turn them into a compelling case for Toast Retail.
  • Educate 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 fit their scale.
  • Own the full sales journey, from lead development and financial structuring to contract negotiation and close, and collaborate with Account Service and Implementation to ensure a seamless handoff on retail installs.
  • Manage lengthy, ambiguous sales cycles, multithread across operations, finance, IT, and merchandising, and develop champions within layered retail organizations.
  • Partner with Legal, Deal Desk, Biz Ops, and Finance to structure deals and negotiate terms aligned with Toast's goals; work with Product, Marketing, and Enablement to address gaps in the Mid Market Retail sales motion and escalate unresolved gaps.
  • Turn learnings from live deals into discovery notes, demo flows, and business case models for future AEs, distinguishing repeatable processes from one-off deals.
  • Bring Mid Market retailers' needs to the product roadmap with specificity and evidence.
  • Optimize for long-term realized revenue by evaluating each deal's financial impact and making thoughtful trade-offs on pricing, discounts, and terms while protecting Toast's bottom line.
  • Maintain high execution, prioritization, and follow-through standards in Salesforce and the broader GTM tech stack, and help establish conversion benchmarks.

Desired Qualifications

  • Experience selling into or operating within grocery, convenience, liquor, or specialty retail.
  • Fluency in retail operations, including inventory depth and SKU management, scan data, shrink, category management, age verification and compliance, fuel, and foodservice.
  • Experience selling into franchised organizations and navigating franchisor and franchisee requirements, buying processes, and stakeholder management.
  • Experience working with cross-functional stakeholders to complete complex RFPs; experience helping write an RFP for a prospect just beginning its evaluation process is a bonus.
  • Experience helping establish a new segment, vertical, or sales motion within an existing company, especially taking an SMB product upmarket.
  • Experience in a fast-paced, high-growth technology environment.

About the Company

Toast

Builds restaurant and retail software and payments

Toast builds a cloud platform that connects point-of-sale terminals, payments and business software for restaurants and retailers. Its Toast Go handheld devices let staff take orders and accept payments beside the customer, while kitchen screens route tickets to the people preparing each meal. Operators manage menus, online orders and employee payroll through connected tools that share real-time information across the front counter and back office. The company earns software subscription fees and transaction-based payment fees, and sells hardware and implementation services. Toast was founded in 2011 and is headquartered in Boston, Massachusetts.

Company size
5,001-10,000
Company stage
IPO
Headquarters
Boston, MA
Founded
2011

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