Sales Director, Enterprise Grocery Retail, Midwest

Flashfood

11d•Remote

About The Position

Flashfood is seeking a Sales Director to lead the expansion into larger and more complex enterprise organizations within the grocery retail sector. This role is for someone who deeply understands the grocery ecosystem, possesses genuine executive presence, and has a proven track record of closing deals with major enterprise retailers. As a senior individual contributor, you will own strategic, enterprise-level sales with large, multi-banner grocery retailers across the US, manage full-cycle enterprise sales, and contribute to shaping Flashfood's sales strategy, process, and culture. This is not a transactional role and requires deep knowledge of grocery operations, executive presence, experience closing complex deals, comfort with long sales cycles, and the ability to build financially grounded business cases. Strong connections within the Midwest grocery region are particularly valued.

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.
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.

Nice To Haves

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.

Responsibilities

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 tool.
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.
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.