This role pays less than
67%
of similar roles. Most pay
$127,500–$210,000
— the shaded band above.
At the midpoint, this role pays about
$144k
versus about
$169k
for comparable roles.
Based on 240 similar postings.
Employer
About Toast, Inc.
Toast is a cloud-based restaurant management platform providing point-of-sale, payment processing, and operations software for the food service industry.
Toast, Inc. currently has
29 open roles
on FindRole.
Listed pay typically runs
$190,000–$304,000
across 29 roles with salary data.
Mid-Market Sales Manager, Retail will join the Toast Retail team to build the commercial motion for expanding into complex upmarket accounts, specifically targeting grocery, liquor, and convenience stores. This player-coach role involves managing a small team of Account Executives while personally closing deals to establish a new sales playbook. The manager will develop discovery frameworks, demo flows, business case models, and executive proposals tailored to multi-location retail buyers with high inventory and SKU demands. Key responsibilities include hiring and coaching a high-performing team, collaborating cross-functionally with Product, Marketing, and Finance to bridge operational gaps, and managing the full sales lifecycle including negotiation and deal structuring. Success requires expertise in MEDDPICC methodology, proficiency in GTM tech stacks, and deep knowledge of retail operations like scan data, shrink, and compliance while navigating a landscape of entrenched incumbent systems.
Manage a personal sales quota while hiring and training a new team of Mid-Market Account Executives.
Build and codify the mid-market sales playbook, including discovery frameworks, demo flows, and business case models.
Lead complex, multi-stakeholder negotiations with grocery, liquor, and convenience store operators.
Collaborate with Product, Marketing, and Finance teams to resolve technical gaps and create repeatable sales motions.
Coach team members on qualification rigor, multithreading, and navigating large retail organizations.
Translate first-hand field experience into scalable training materials and internal process improvements.
Advocate for the mid-market customer's needs to influence the product roadmap with specific evidence.
Monitor the competitive landscape to position Toast Retail effectively against established incumbents.
What we're looking for
5+ years of sales experience in a sourcing and closing role for Mid-Market or complex, multi-stakeholder deals.
3+ years of sales leadership experience with a proven record of building quota-achieving teams and 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.
Ability to influence cross-functional partners like Product, Marketing, and Finance without formal authority over them.
Strong written and verbal communication skills to engage executive stakeholders and negotiate complex pricing.
Knowledge of US credit card processing fundamentals.
Experience standing up a new segment or moving an SMB product upmarket (preferred); experience in grocery, convenience, liquor, or specialty retail (preferred).