Jobs › Toast

Senior Software Engineer, Retail

Toast · Remote · R & D : Engineering : Retail

Posted Sep 25, 2026 · We last checked this listing on Oct 6, 2026

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Likely interview questions for this role

Written from this job description, not a generic list. Each one notes what the interviewer is really checking.

About your past

Tell me about a time you went to the customer's actual workplace to understand a problem. What did you learn that you wouldn't have learned otherwise?

What they are checking: Whether they value seeing real workflows, since the posting says to expect store visits and talking with operators.

Tell me about a feature you shipped quickly from early customer feedback and then had to change.

What they are checking: Comfort with fast iteration and learning, which this early-stage vertical depends on.

How do you work with product leads to decide what's worth building next in a new vertical?

What they are checking: Whether they bring engineering judgment to prioritization instead of only taking tickets.

How do you explain a technical limitation to a store operator who just wants it to work?

What they are checking: Plain, respectful communication with non-technical customers the team talks to directly.

What would you do

A convenience store chain asks for a back-office tool the platform doesn't have. How do you decide whether to build it for them or build something general?

What they are checking: Balancing one large customer's need against building reusable platform features for a growing vertical.

A store operator tells you the system is too slow at checkout during the morning rush. How do you dig in?

What they are checking: Turning a vague operator complaint into measured performance work that targets the real bottleneck.

About the work

A large grocery chain needs to sync tens of thousands of items and prices from their own system into Toast every night. How would you design that integration?

What they are checking: Handling big catalog syncs with validation, partial failures and conflict rules at grocery scale.

How is retail different from restaurants when it comes to inventory, barcodes and pricing, and how would that affect the data model?

What they are checking: Whether they think about domain differences like SKUs, weighted items and promotions before reusing restaurant assumptions.

How do you make sure a price change pushed from back office reaches every register in every store correctly?

What they are checking: Consistency and verification in distributed systems where a wrong price costs the store money or trust.

What makes a third-party integration reliable over years, not just on launch day?

What they are checking: Thinking about versioning, monitoring, retries and clear ownership for long-lived integrations.

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The full job description

As published by Toast.

Location(s):&nbsp; US (remote), Boston (hybrid), or New York (hybrid) - EST preferred &nbsp; Bready* to make a change? 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. The Retail organization at Toast is focused on building foundational technology to support a rapidly expanding vertical. We emphasize early learnings and remain closely aligned with our customers, engaging in frequent conversations with our initial retail partners to understand their needs, pain points, and feature requests. This direct feedback loop allows us to rapidly iterate and ensures we are building the right product for the market. As one of the fastest-growing verticals at Toast, we offer an opportunity to have a significant impact on the company's future growth. We’re looking for engineers to help make our product work for our largest customers. Think large grocery stores and your favorite local convenience store chain. With their larger scale bring additional needs for integrations and backoffice tools, beyond what the platform offers today. This team works closely with customers&nbsp; — expect to visit stores and talk directly with operators to deeply understand their workflows.&nbsp; About this roll* (Responsibilities) • Work closely with engineering and product leads to identify high-impact opportunities in the domain • Plan, scope, and prototype solutions from design to rollout. You need to think about each feature as a whole, not just the side of the stack you work in • Make technical decisions and recommendations that will lay the foundation for the future of our retail platform • Stay in tune with customer needs by hearing direct customer feedback and staying abreast of industry trends • Deploy AI-native experiences that delight our customers, powered by Toast IQ. Do you have the right ingredients*? (Requirements) • Growth mindset with an emphasis on learning and self/team-improvement • 6+ years experience building and shipping production software to customers • Experience with Java , Kotlin , or other object oriented programming languages • Respectful, empathetic, and humble • Passionate about making users happy and seeing people use your product in the wild. • Startup mindset and comfort with ambiguity • Flexible in using different tech stacks and languages • Comfortable with testing methodologies and frameworks&nbsp; 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&nbsp; 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&nbsp;<a class="c-link" href="https://careers.toasttab.com/toast-benefits" target="_blank" data-stringify-link="https://careers.toasttab.com/toast-benefits" data-sk="tooltip_parent" data-remove-tab-index="true">https://careers.toasttab.com/toast-benefits . The base salary range for this role is listed below. The starting salary will be determined based on skills, experience, and geographic location. In addition to base salary, our total rewards components include cash compensation (overtime, bonus/commissions if eligible), equity, and benefits. You can learn more about how we align pay with local labor markets in our Geographic Pay Zone Philosophy . Zone A $159,000 &mdash; $254,000 USD Zone B $138,000 &mdash; $221,000 USD Zone C $125,000 &mdash; $200,000 USD 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. We ask that you complete interviews and assessments on your own, without real-time AI tools, recording, or transcription bots, unless we tell you otherwise in advance. To learn more: https://careers.toasttab.com/ai-in-hiring Our Approach to Hybrid Working 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 hospitality community, regardless of location. Please visit the Locations page on our career site to learn more about our in-office expectations by region:&nbsp; https://careers.toasttab.com/locations-toast People Are the Secret Ingredient in Our Recipe for Success At Toast, our employees are our secret ingredient—when they thrive, we thrive. The restaurant industry brings together people with a wide range of backgrounds, experiences, and perspectives, and we value that same breadth at Toast. We strive to build a culture grounded in authenticity, respect, and humility, where every Toaster has a real opportunity to grow, contribute, and do their best work—raising the bar in delivering exceptional experiences for our customers and each other. 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.

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