Director of Retail Engineering

Toast creates technology to help restaurants and local businesses succeed in a digital world, helping business owners operate, increase sales, engage customers, and keep employees happy.

As the Director of Engineering for Retail, you will be the primary architect and operator of Toast’s highest-growth business unit - a $100M+ "startup" currently doubling year-over-year. You aren't just managing squads; you are responsible for building a configurable, high-scale Retail Platform that serves the unique needs of Grocery and Convenience Store personas while solving the massive data integrity challenges of global inventory. We are moving away from general-purpose tools to build a resilient, offline-first engine that handles everything from fuel payments at the pump to autonomous, agentic inventory replenishment.

A day in the life (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

What you'll need to thrive (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

AI at Toast

At Toast, one of our company values is that we're hungry to build and learn. We believe learning new AI tools empowers us to build for our customers faster, more independently, and with higher quality. We provide these tools across all disciplines, from Engineering and Product to Sales and Support, and are inspired by how our Toasters are already driving real value with them. The people who thrive here are those who embrace changes that let us build more for our customers; it’s a core part of our culture.

Our Total Rewards Philosophy 
We strive to provide competitive compensation and benefits programs that help to attract, retain, and motivate the best and brightest people in our industry. Our total rewards package goes beyond great earnings potential and provides the means to a healthy lifestyle with the flexibility to meet Toasters’ changing needs. Learn more about our benefits at https://careers.toasttab.com/toast-benefits.

The base salary range for this role is listed below. The starting salary wi