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Toast

Mid-Market Sales Manager, Retail

Toast · Remote, United States

Posted 21 days ago

or apply directly on Toast's site. We never take the application ourselves.

Is this posting real?

This role has been open
21 days
Toast's roles stay open a median of 42 days
Reposted
No
Salary listed
No
0% of Toast's roles list one
Ghost-job risk at Toast
low
0 stale, 57 reposted of 346 open
Hiring momentum
625 roles opened in the last 90 days
↑ up vs. the prior 90 days
Last confirmed on the employer's board
2026-09-17

Measured from postings appearing on and disappearing from Toast's own greenhouse board since 2026-08-03. Full hiring picture for Toast.

About this role

As the Mid-Market Sales Manager for Toast Retail, you will lead a team focused on selling to complex, multi-location retail accounts such as grocery and convenience stores. Your role involves building a new sales process from the ground up, coaching your team, and directly closing deals while collaborating with various departments to ensure a successful sales motion. This position requires a proactive approach to develop strategies for engaging with sophisticated buyers and navigating the unique challenges of the retail sector.

Our read on this posting3.2out of 5
benefits
2/5
freshness
4/5
career value
5/5
role clarity
5/5
pay transparency
0/5

Scored from the posting itself — how clearly the role is described, how much it says about pay and benefits, and how recently it was listed. Not a judgement of Toast as an employer.

What you need

  • 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
  • Strong written and verbal communication, including the ability to hold the room with executive stakeholders and negotiate complex pricing arrangements

Nice to have

  • 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

What you get

  • Competitive compensation and benefits programs
  • Total rewards package includes cash compensation, equity, and benefits
  • Uncapped commissions

Worth weighing

  • This role requires building a new sales process from scratch, which may involve ambiguity and uncertainty
  • Expect travel up to 40% of the time
  • The role is a player-coach position in the first year, meaning you will need to balance individual sales with team management

Summarised from Toast's posting. Read the full original.

Listed by Toast on their greenhouse job board, last confirmed open on 2026-09-17. PitchMeAI is not the employer.

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