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Sales Director, Enterprise Grocery Retail, Midwest
Sales
💰 Salary Not shared
📊 Market 10,000 CAD–16,667 CAD/mo (120,000 CAD–200,004 CAD/yr)
About the Company
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. Flashfood exists to reduce food waste at scale while helping families save on groceries. We partner with retailers to unlock value from inventory that would otherwise go unsold, benefiting shoppers, stores, and the planet. If you understand grocery deeply, carry real executive presence, have closed with major enterprise retailers before, and want to drive meaningful growth, we would love to connect. Flashfood is an equal opportunity employer and is committed to building a diverse, inclusive, and equitable workplace. We welcome candidates from all backgrounds and experiences, and we're dedicated to creating an environment where everyone feels supported and empowered to do their best work.
About the Role
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: 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.
Responsibilities
- ● 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.
- ● 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
- ● 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
- ● 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
Requirements
- ● 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
- ● 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
- ● 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
- ● 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
- ● Command credibility the moment you're in a room with senior retail executives
- ● Polished, confident communicator, equally strong in written and verbal executive settings
- ● Skilled, composed negotiator of complex, multi-year enterprise contracts
- ● Comfortable building and presenting financial models and ROI narratives directly to C-suite stakeholders
- ● Brings instant credibility the moment they walk into a grocery boardroom
- ● Speaks the language of retail operators fluently
- ● Has already proven they can close with major enterprise retailers
- ● Is motivated by performance, ownership, and mission
- ● Wants to help define a category-leading sales function, not just carry a number
Benefits
- ● Performance-driven compensation aligned with enterprise impact
- ● Comprehensive health, dental, and vision benefits
- ● 100% remote
- ● Learning & development budget
- ● A defining, senior-level role in scaling a mission-driven company into its next stage of enterprise growth
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