Mid-Market Sales Manager, Retail

This is a fully remote position, open to applicants in United States.

📋 Description

• Lead a dedicated team of Mid-Market Account Executives focused on multi-location grocery, liquor, and convenience store operators.

• Achieve and deliver an individual sales quota in the first year while recruiting, onboarding, and ramping up the team, transitioning to a collective team target as the team grows.

• Hire, cultivate, inspire, and oversee a quota-achieving Mid-Market sales team from inception.

• Develop and formalize the Mid-Market Retail sales process, encompassing discovery frameworks, demo sequences, business case models, mutual action plans, and executive proposals.

• Implement a structured sales process and coach on qualification rigor, multithreading, and champion development.

• Manage live Mid-Market deals from start to finish and translate insights into repeatable team playbooks.

• Participate in discovery calls, site visits, and store walkthroughs with representatives.

• Take charge of pipeline generation, executive meetings, value proposition development, deal structuring, negotiation, and closing.

• Collaborate with Product, Marketing, Enablement, Deal Desk, Finance, and Onboarding to create a repeatable Mid-Market strategy.

• Integrate Mid-Market retailer insights into the product development roadmap.

• Provide accurate forecasts despite limited historical data.

• Engage in competitive RFPs and assess opportunities.

• Utilize the GTM technology stack to set conversion benchmarks and generate reports.

• Differentiate between repeatable processes and one-off deals.

• Keep an eye on the competitive landscape and position Toast Retail against competitors.

• Report directly to the VP of Sales at Toast Retail.

⛳️ Requirements

• Over 5 years of sales experience in a sourcing and closing role, with a proven track record in Mid-Market or complex, multi-stakeholder deals.

• More than 3 years of sales leadership experience in building and nurturing quota-achieving teams and generating outbound pipelines.

• Expertise in complex deal development, financial structuring, negotiation, and closing deals with both new and existing clients.

• Proficient in MEDDPICC or a similar qualification methodology.

• Strong pipeline management and forecasting capabilities.

• Recent credibility with Mid-Market buyers and a willingness to remain actively involved in sales.

• A founder's mindset with the ability to navigate ambiguity effectively.

• Ability to influence cross-functionally with Product, Marketing, and Operations teams.

• Excellent written and verbal communication skills, along with experience managing executive stakeholders and complex pricing negotiations.

• Comfortable teaching customers and team members about the fundamentals of US credit card processing.

• Experience in establishing a new segment, vertical, or initiative, particularly in taking an SMB product to the mid-market level.

• Background in selling to or working within grocery, convenience, liquor, or specialty retail sectors.

• In-depth knowledge of retail operational realities, including inventory management, SKU oversight, scan data, shrinkage, category management, age verification and compliance, as well as fuel and foodservice.

• Experience in a fast-paced, high-growth technology environment.

• Demonstrated success in building a high-performing culture.

🏝️ Benefits

• Competitive compensation and benefits packages.

• Cash compensation, inclusive of overtime, bonuses, and commissions if eligible.

• Equity participation if eligible.

• Uncapped commissions.

• Flexible benefits designed to support a healthy lifestyle and adapt to changing needs.

• Access to AI tools across various disciplines.

• Hybrid work model that values individual preferences.

• Reasonable accommodations available for individuals with disabilities.