Senior Director of Product, Retail

Flashfood • Canada, KY

7d • Remote

About The Position

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.

We're looking for a Senior Director of Product, Retail to lead our Retail organization, a cross-functional team of engineers, product managers, and designers building the platform our grocery partners run on: the partner app, store onboarding and activation, catalog integration, dashboards and reporting, and dynamic pricing. This is as much a general manager role as a product role. You'll own the roadmap and business goals end to end, and be the first product leader at Flashfood with deep retail domain expertise.

This role is for product leaders with meaningful grocery or retail experience. Our roadmap decisions today are hypotheses — your job is to turn them into knowledge, backed by data. You're a builder and an owner: comfortable in the room with retail executives and engineers alike, and you know the best products come from understanding the operator's day, not a feature list.

You're ideal for this role if you:
Have genuine fluency in retail or grocery — merchandising, store ops, catalog data, and how enterprise grocers make decisions
Lead with evidence: vet opportunities with data before committing a team, then drive hard to ship
Are direct, low ego, and energized by defining a category in a lean, fast-moving organization

Requirements

• 10+ years of product management experience, with 5+ years managing cross-functional teams against shared business goals — ideally in B2B or enterprise software.
• Direct experience working for or with grocery or retail companies: merchandising, store operations, item-level catalog data, and how retail organizations make decisions.
• Strong data fluency — integration patterns common in retail, and a track record of making product decisions based on evidence, not intuition.
• Proven ability to take ambiguous, high-stakes product areas from hypothesis to shipped product with measurable business impact.
• Experience working directly with enterprise customers and executive stakeholders, translating operational reality into product strategy.
• Comfort operating in a lean, fast-moving organization where leaders are hands-on.

Nice To Haves

• Experience with markdown optimization, pricing systems, inventory management, or shrink-adjacent retail technology.
• Familiarity with AI-assisted and agentic product development: products that incorporate LLM agents, automation of operational workflows, or ML-driven pricing and personalization.
• Experience building data or insights products for enterprise customers.
• Prior experience as the first senior product hire in a domain, building the function around you.

Responsibilities

• Define and drive the roadmap for Flashfood's retail platform: partner app, onboarding and activation, catalog integration, dashboards and reporting, and dynamic pricing.
• Bring deep retail domain knowledge into every planning cycle so roadmap calls are grounded in how grocers actually operate.
• Vet the biggest opportunities with data, size them, and sequence them — your first two quarters set the build plan and the hires that follow.
• Directly manage the Retail pod — engineers, product managers, and designers — with an engineering lead as your player-coach on architecture.
• Own the pod's business goals: stores activated, items posted, partner adoption, and the revenue tied to them.
• Sequence team growth behind validated opportunities, and set the bar across functions: crisp specs, sound tradeoffs, measurable outcomes, honest post-launch reads.
• Work directly with enterprise grocery partners — store associates to corporate buyers — to understand operations and translate them into product.
• Support the sales motion with product depth: discovery sessions, executive demos, and the data story that wins national rollouts.
• Own the product side of activation: shrink the path from signed contract to launched store from months to weeks.
• Partner with our data and ML team to embed pricing intelligence and demand signals into the retail product surface.
• Champion AI-native product development — agents that do real operational work for retailers, not dashboards for their own sake.
• Operate as a senior leader in EPD: raise hard questions early, advocate for the right tradeoffs, and bring people along with you.

Benefits

• Competitive salary, equity, and comprehensive benefits
• 100% remote work with flexibility and trust
• Mission-driven work that reduces food waste and expands access to affordable food
• A fast-growing, collaborative team with big ambitions
• Real opportunities for career growth

What This Job Offers

• Job Type: Full-time
• Career Level: Senior
• Education Level: No Education Listed