Sales Director – Enterprise Grocery Retail

This is a fully remote position, open to applicants in Illinois, +3 more states.

📋 Description

• Take ownership of strategic, enterprise-level sales with large, multi-banner grocery retailers throughout the US.

• Manage the complete sales cycle from market strategy and executive engagement to negotiation and closure.

• Identify and prioritize high-value grocery targets within the territory.

• Create account penetration strategies customized for each organization.

• Map buying committees across various functions, including operations, merchandising, finance, digital, sustainability, and executive leadership.

• Establish and nurture executive-level relationships within complex retail organizations.

• Lead discovery efforts focused on grocery operational challenges such as shrinkage, labor limitations, margin pressures, inventory management, and digital engagement.

• Convert retailer pain points into measurable, board-ready business cases.

• Develop and present executive-ready proposals that include ROI, financial modeling, and implementation plans.

• Manage lengthy, multi-region sales cycles and navigate procurement, legal, data security, and operational stakeholders.

• Structure enterprise agreements that support scalable, long-term partnerships.

• Independently secure large, multi-region or enterprise-wide deals with major grocery retailers.

• Assist in defining and refining Flashfood’s enterprise sales process, playbooks, and culture.

• Collaborate with Marketing, Product, Implementation, and Customer Success teams.

• Provide executive-level field insights to guide product and go-to-market strategies.

• Maintain CRM integrity, forecasting precision, and pipeline management.

⛳️ Requirements

• Profound and credible understanding of grocery organizations, including merchandising, operations, shrinkage, and store execution.

• Executive presence when interacting with C-suite and VP-level audiences.

• Proven and verifiable track record of closing complex deals with major enterprise retailers.

• Experience in leading extended, multi-threaded sales cycles involving procurement, legal, and data security stakeholders.

• Ability to construct executive-level, financially grounded business cases.

• Strong connections within the grocery sector, particularly with leading grocers in the Midwest, including Michigan, Ohio, Illinois, Indiana, and Pennsylvania.

• Extensive experience working within or selling to large grocery retailers.

• Existing network of C-suite and VP-level decision-makers across regional or national grocery chains.

• Over 10 years of enterprise sales experience, ideally in grocery retail, CPG-tech, retail-tech, or related fields.

• A demonstrated history of successfully closing complex six- and seven-figure deals with major enterprise retailers.

• Consistent record of meeting or surpassing quota at a senior/Director level.

• Experience in selling within markets characterized by lengthy cycles and multiple stakeholders.

• Polished and confident written and verbal communication skills in executive contexts.

• Skilled negotiator of complex, multi-year enterprise contracts.

• Comfortable in building and presenting financial models and ROI narratives directly to C-suite stakeholders.

🏝️ Benefits

• Compensation driven by performance, aligned with enterprise impact.

• Comprehensive health, dental, and vision insurance.

• Fully remote work environment.

• Budget for learning and development.

• Senior-level position in a mission-driven company poised for its next stage of enterprise growth.