Director of Retail Engineering

Toast creates technology to help restaurants and local businesses succeed in a digital world. As the Director of Engineering for Retail, you will architect and operate a high-scale Retail Platform that addresses the unique needs of Grocery and Convenience Store personas while managing complex data integrity challenges.

Responsibilities:

• Own the Retail Technical Strategy: Mandate to move beyond siloed feature development to build a unified, extensible retail core that supports both Grocery and C-Store personas at scale
• Architect for Resilience: Ensure "Zero-Downtime" at the edge; you will oversee the transition to a robust, offline-first architecture that keeps high-volume grocers running regardless of connectivity
• Deploy Autonomous Systems: Lead the move from manual inventory management to AI-driven autonomous systems, solving complex "non-deterministic" inventory and supply chain conflicts across thousands of locations
• Raise Talent Density: Aggressively uplevel the engineering organization by identifying and attracting top-tier talent and coaching existing managers to operate as high-autonomy owners
• Own the Outcome: Partner with Product and UX to drive the P&L of the Retail technical stack, managing the immediate delivery of the Retail POS and Purchasing & Receiving squads while architecting the long-term roadmap for Fuel and Catalog management
• Eliminate Tech Debt as Strategy: Proactively identify and dismantle "special-case" code to ensure the retail platform remains lean, fast, and configurable for any hybrid food-retail model
• Champion the use of AI tools and practices to accelerate development, improve team velocity, and pioneer new ways of building - setting the bar for what it means to be an AI-first engineering organization

Requirements:

• Platform-First Mindset: You have a track record of building configurable platforms rather than just collections of features
• Systems Architect Background: Deep experience with distributed systems and edge computing. You know how to build software that is bulletproof in high-pressure, real-world physical environments
• High-Growth 'Builder' Scar Tissue: You have led engineering teams through the '1-to-10' scale phase at a high-growth startup and know how to maintain velocity while increasing technical rigor
• Obsession with Data Integrity: Experience solving complex inventory, supply chain, or financial reconciliation problems where data accuracy is the difference between a successful business and a failed audit
• Zero Tolerance for Mediocrity: You hold an incredibly high bar for talent and execution. You are a 'leader of leaders' who empowers managers but stays close enough to the metal to spot architectural flaws
• Strategic Influence: You can navigate high-stakes XFN relationships, moving beyond 'feature requests' to influence the fundamental business strategy through technical innovation