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 technical owner of Toast’s highest-growth business unit - a $50M+ "startup" currently doubling year-over-year.

We’re bringing the same all-in-one platform beloved by restaurants to a whole new segment of businesses. You are responsible for building a delightful, flexible, and scalable platform that serves the unique needs of businesses across a wide variety of retail personas. You will own everything from agentic inventory automation, to optimizing the POS for high-throughput checkout experiences, and everything in between.

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 a wide variety of retail personas at scale
• Architect for Resilience: Ensure high availability and blazing fast performance at the edge; you will oversee the infrastructure that keeps our high-volume retailers up and running regardless of connectivity
• Deploy Autonomous Systems: Lead the move from manual and labor-intensive inventory management to AI-driven autonomous systems, saving hours of time and unlocking new operational efficiencies for thousands of customers
• Raise Talent Density: 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 Design to drive the P&L of the Retail business, managing the immediate delivery of the Retail POS and Purchasing & Receiving squads while developing a long-term strategy for the Grocery persona

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" DNA: 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
• Drives Exceptional Outcomes: 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 cross-functional 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.