Sales Director, Enterprise Grocery Retail, Midwest

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
• 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

What Sets This Role Apart

This is a high-impact, high-visibility role with direct influence on company growth and on how Flashfood's enterprise sales function is built. We are looking for someone who:

• 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

What We Offer

• 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

Our Mission

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.