Why This Job is Featured on The SaaS Jobs
This Director of Retail Engineering role stands out in SaaS because it sits at the intersection of platform software and real world commerce constraints. Toast is positioning Retail as a high growth business unit with its own platform mandate, which is a common pattern in larger SaaS companies building new vertical products inside an established ecosystem. The emphasis on offline first resilience, edge reliability, and data integrity reflects the operational demands of SaaS that must perform in physical environments, not just in browsers.
From a SaaS career perspective, the remit signals deep exposure to the problems that define durable platforms: multi persona configurability, shared core services, and reducing special case logic as the product surface area expands. Ownership that spans technical strategy, cross functional partnership, and outcome accountability maps well to senior SaaS leadership paths where architecture decisions directly shape product velocity and commercial viability. Experience guiding AI enabled engineering practices also translates across modern SaaS orgs experimenting with new development workflows.
This role is best suited to a leader who prefers building foundational systems over overseeing incremental feature delivery. It fits someone comfortable balancing near term execution with long horizon platform design, and who can operate as a leader of leaders while staying close enough to technical details to spot structural risks early.
The section above is editorial commentary from The SaaS Jobs, provided to help SaaS professionals understand the role in a broader industry context.
Job Description
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.
How Toast Uses AI in its Hiring Process
Throughout the hiring process, our goal is to get to know you. We use AI tools to support our recruiters and interviewers with tasks like note-taking, summarization, and documentation of interviews to ensure they can be fully focused on your conversation. All hiring decisions are made by people.
Diversity, Equity, and Inclusion is Baked into our Recipe for Success
At Toast, our employees are our secret ingredient—when they thrive, we thrive. The restaurant industry is one of the most diverse, and we embrace that diversity with authenticity, inclusivity, respect, and humility. By embedding these principles into our culture and design, we create equitable opportunities for all and raise the bar in delivering exceptional experiences.
We Thrive Together
We embrace a hybrid work model that fosters in-person collaboration while valuing individual needs. Our goal is to build a strong culture of connection as we work together to empower the restaurant community. To learn more about how we work globally and regionally, check out: https://careers.toasttab.com/locations-toast.
Apply today!
Toast is committed to creating an accessible and inclusive hiring process. As part of this commitment, we strive to provide reasonable accommodations for persons with disabilities to enable them to access the hiring process. If you need an accommodation to access the job application or interview process, please contact candidateaccommodations@toasttab.com.
------
For roles in the United States, it is unlawful in Massachusetts to require or administer a lie detector test as a condition of employment or continued employment. An employer who violates this law shall be subject to criminal penalties and civil liability.
