Jobs › Toast

Principal Software Engineer, Tech Lead, Retail

Toast · Remote · R & D : Engineering : Retail

Posted Sep 9, 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 set a multi-year technical direction for a platform other teams depended on. How did you get buy-in?

What they are checking: Whether they can lead architecture at an organizational level, which is what separates principal from staff.

Describe the worst production incident you've owned. What did you change afterward?

What they are checking: Whether they learn from failure honestly and turn it into lasting fixes rather than blame.

What would you do

A pricing update for a 100-location enterprise goes out and 12 locations end up on the old price. How do you investigate and how do you make sure it never happens silently again?

What they are checking: Whether they think about partial failure, detection and reconciliation instead of assuming every publish succeeds fully.

Other engineering teams want to build on your platform but each wants something custom. How do you decide what goes into the platform and what stays with them?

What they are checking: Whether they protect the platform's coherence while still serving internal customers well.

You disagree with a senior leader's preferred architecture for the next phase. How do you handle it?

What they are checking: Whether they can challenge leadership with evidence and then commit fully once a decision is made.

About the work

Your service is the highest-trafficked at Toast and pushes menu and pricing changes live. How would you design publishing so a change reaches thousands of devices consistently without taking anything down?

What they are checking: Whether they can reason about consistency, fan-out and rollback in a system where failure stops restaurants from taking orders.

How would you build change management so customers can stage, review and roll back configuration changes before they go live?

What they are checking: Whether they can design versioning and approval flows that give customers real confidence instead of a cosmetic preview.

Toast is expanding into Ireland and other countries. What changes in a configuration platform when you add new currencies, tax rules and time zones?

What they are checking: Whether they anticipate internationalization problems early instead of discovering them in production.

How do you approach load testing and capacity planning for a service where a traffic spike at dinner rush can't be allowed to fail?

What they are checking: Whether they plan for peak real-world patterns and know how to prove capacity before it's needed.

How would you measure whether the platform is getting more reliable quarter over quarter?

What they are checking: Whether they define meaningful service objectives instead of vanity uptime numbers.

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The full job description

As published by Toast.

Location(s): US (remote), Boston (hybrid), or New York (hybrid) -&nbsp; 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 back-office 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) • Design, build, deploy, and maintain highly resilient and scalable systems that are critical to our customers’ success • Define and drive long-term technical architecture and strategy across the entire organization, aligning executive business goals with platform capabilities. • Design solutions that anticipate and accommodate future needs while considering tradeoffs • Effectively communicate technical direction • Sponsor and mentor senior engineering talent (Staff and Senior Staff engineers) to grow the next generation of technical leaders across Toast. • Act as a force multiplier in improving engineering productivity • Diagnose performance bottlenecks and implement optimizations • Leverage cutting edge AI tools to enhance your development workflow, improve velocity, and help pioneer new approaches to building - contributing to a culture of innovation and productivity across the team. Do you have the right ingredients*? (Requirements) • 9+ years experience building and shipping production software to customers • Experience with Java, Kotlin, or other object oriented programming languages • Approach your work with humility, empathy, and deep respect for your peers • Articulate sophisticated project roadmaps and empower engineering cohorts to drive them toward fruition • Startup mindset in driving initiatives and ability to find order in ambiguity • Passionate about making users happy and seeing people use your product in the wild. • Embody a growth-oriented mindset focused on continuous elevation of your craft and domain • Establish yourself as a trusted technical authority capable of making decisions that secure both immediate wins and long-term strategic goals 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 $230,000 &mdash; $368,000 USD Zone B $200,000 &mdash; $320,000 USD Zone C $180,000 &mdash; $288,000 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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