Mid-Market Sales Manager, Retail

Toast

3d•$165,000 - $338,000•Remote

About The Position

Toast is expanding its innovative POS platform into new food and beverage concepts, including convenience stores, grocery stores, and bottle shops. This role is crucial for building the commercial strategy as Toast Retail moves towards serving more complex, upmarket accounts. The Manager of Mid-Market Sales will lead a team of Account Executives focused on multi-location retail clients, particularly in the grocery, liquor, and convenience sectors. These accounts present unique challenges, including sophisticated buying committees, regulatory compliance, extensive inventory management needs, and entrenched incumbent systems. The successful candidate will be responsible for developing and implementing a new sales motion tailored to these complex environments, as there is no existing playbook for Mid-Market Retail at Toast. This involves forming hypotheses, testing them in the field, and creating a repeatable process for future sales teams. The role requires significant cross-functional collaboration with Product, Marketing, Enablement, Deal Desk, Finance, and Onboarding teams to address product gaps, refine messaging, develop training, structure new offerings, and manage complex implementations. It is a player-coach role in the first year, where the manager will carry an individual quota while hiring and building the team, transitioning to a team quota as the team scales. The goal is to draw from first-hand experience to create a robust sales playbook. The position reports to the VP of Sales, Toast Retail, and is a remote opportunity with up to 40% travel.

Requirements

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.
A closer who is also a builder. You are recently and personally credible in front of a Mid-Market buyer, and you are not looking for a role where you stop selling.
A genuine founder's mindset. You are energized rather than frustrated by ambiguity, and your instinct when a process is missing is to write it rather than ask for it.
Exceptional cross functional influence. You have a history of getting Product, Marketing, and Operations partners to move on your priorities without owning them.
Strong written and verbal communication, including the ability to hold the room with executive stakeholders and negotiate complex pricing arrangements.
Comfortable educating customers and team members on the fundamentals of US credit card processing.

Nice To Haves

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.

Responsibilities

Carry and deliver an individual quota in year one (player-coach) while you hire, onboard, and ramp your team, transitioning to a full team number as your team scales.
Hire, develop, motivate, and manage a quota achieving Mid-Market sales team from the ground up, setting the bar for talent in a brand new function.
Build and codify the Mid-Market Retail sales process: discovery frameworks, demo flows, business case models, mutual action plans, and executive proposals tailored to grocery, liquor, and convenience buyers.
Run a disciplined sales process and coach your team on qualification rigor, multithreading, and champion development inside complex retail organizations.
Own live Mid-Market deals end to end yourself, then convert what you learn into discovery frameworks, demo flows, business cases, and proposals the team can run.
Get in the field. Join discovery calls, sit in on site visits, and walk stores with your reps so the playbook you write is grounded in what actually happens in front of a customer.
Own all stages of the sales lifecycle with your team: pipeline generation, executive meetings, value proposition development, deal structuring, negotiation, and close.
Partner across Product, Marketing, Enablement, Deal Desk, Finance, and Onboarding to close the gaps that stand between us and a repeatable Mid-Market motion, and escalate the ones you cannot close yourself.
Bring the voice of the Mid-Market retailer back into the product roadmap with specificity and evidence, not anecdotes.
Forecast accurately in a business with little historical data, and be honest about what you know versus what you are still learning.
Assess and engage in competitive RFPs.
Leverage GTM tech stack to run an efficient, AI-anchored motion: establish the conversion benchmarks that do not exist yet, and report on them credibly.
Distinguish repeatable process from one off hero deals, and build only the former into the playbook.
Stay close to the competitive landscape across grocery, liquor, and convenience technology, and position Toast Retail sharply against incumbents.