Sales Director, Enterprise Grocery Retail, Midwest

About Us Our company is on a mission to reduce food waste and make high-quality, affordable food accessible to everyone. Through our innovative app-based marketplace, we connect shoppers with discounted perishable items while helping retailers turn would-be waste into revenue and meaningful environmental impact. We’re growing quickly across North America and partnering with retailers of all sizes to expand our reach. If you’re passionate about creating real change for people and the planet, we’d love for you to join us. Your work here will directly contribute to a mission that helps families save money, reduces waste, and builds a more sustainable future. The Role and Context Flashfood is the app for grocery's best deals. We partner with leading grocery retailers across North America to sell fresh food nearing its best-by date at a discount, helping shoppers save money while preventing good food from going to waste. We help drive incremental revenue, improve shrink outcomes, increase basket size, and deepen customer loyalty, all while advancing sustainability goals. As we expand into larger and more complex enterprise organizations, we are hiring a Sales Director to lead that expansion. Someone who understands the grocery ecosystem deeply, carries genuine executive presence, and has a track record of closing with major enterprise retailers. As Sales Director, you will own strategic, enterprise-level sales with large, multi-banner grocery retailers across the US. This is a senior individual-contributor leadership role: you will run full-cycle enterprise sales while also helping shape Flashfood's sales strategy, process, and culture as we scale into our next tier of partnerships. This role is not transactional and is not an entry point into enterprise sales. It requires, as hard requirements:     Deep, credible knowledge of how grocery organizations actually operate: merchandising, operations, shrink, and store execution     Executive presence that reads as credible the moment you're in front of a C-suite or VP-level audience     A demonstrated, verifiable history of closing complex deals with major enterprise retailers     Comfort leading long, multi-threaded sales cycles involving procurement, legal, and data security stakeholders     The ability to think beyond features and build executive-level, financially grounded business cases     Deep grocery connections with leading grocers across the Midwest region, especially in Michigan, Ohio, Illinois, Indiana, and Pennsylvania. You will own the full sales cycle, from market strategy and executive engagement through negotiation and close, and will partner with leadership to influence how Flashfood's enterprise motion evolves. What You'll Do Strategic Enterprise Development     Identify and prioritize high-value grocery targets across your territory     Develop account penetration strategies tailored to each organization's structure, priorities, and economics     Map buying committees across operations, merchandising, finance, digital, sustainability, and executive leadership     Build and sustain multi-threaded, executive-level relationships within complex retail organizations Industry-Led, Executive Sales Execution     Lead discovery grounded in real grocery operational challenges (shrink, labor constraints, margin pressure, inventory management, digital engagement)     Translate retailer pain points into quantifiable, board-ready business cases     Position Flashfood as a strategic lever for enterprise performance, not solely a shrink too     Develop and deliver executive-ready proposals with clear ROI, financial modeling, and rollout plans, directly to VP and C-suite audiences Complex Deal Leadership & Close     Drive long, multi-region sales cycles with discipline and clarity     Navigate procurement, legal, data security, and operational stakeholders     Structure enterprise agreements that support scalable, long-term partnerships     Independently close large, multi-region or enterprise-wide deals with major grocery retailers Sales Leadership & Cross-Functional Influence     Help define and refine Flashfood's enterprise sales process, playbooks, and culture as the team scales     Partner closely with Marketing, Product, Implementation, and Customer Success to align enterprise strategy     Bring structured, executive-level feedback from the field to inform product and go-to-market decisions     Maintain disciplined CRM hygiene, forecasting accuracy, and pipeline management What You’ll Bring Deeply Connected in Grocery (Required)     Extensive experience inside, or selling into, large grocery retailers     Fluent in the internal dynamics of merchandising, operations, and store execution     An existing network of C-suite and VP-level decision-makers across regional or national grocery chains Strategic Thinker     You think beyond immediate deals to enterprise-wide rollout and long-term value creation     You connect operational improvements directly to financial outcomes     You build executive-level narratives grounded in data, not just product features Proven Enterprise Closer (Required)     10+ years of enterprise sales experience, with strong preference for grocery retail, CPG-tech, retail-tech, or adjacent sectors     Demonstrated, referenceable success closing complex, six- and seven-figure deals with major enterprise retailers     A consistent history of meeting or exceeding quota at a senior/Director level Operator in Challenging Environments     Experience selling in markets with long cycles and multiple stakeholders     You maintain momentum and pipeline discipline even when deals stall     You operate with resilience, ownership, and executive-level judgment Executive Presence (Required)     Command credibility the moment you're in a room with senior retail executives