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Mid Market Account Executive, Toast Retail

Toast

Remote · United States$6,333–28,917 gross/mofull-timeToast Careers

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.

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.

Languages

    Work format
    Remote
    Seniority
    Mid
    Posted
    2 Sept 2026
    Last verified
    In the last 5 days

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