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Staff Software Engineer, Tech Lead, Payroll Onboarding

Toast · Remote · R & D : Engineering : Team

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 deep technical initiative you led across several teams. How did you get people who didn't report to you to commit to it?

What they are checking: Whether they lead through influence and clear technical reasoning, which is what a staff tech lead does daily.

Describe a time you pushed back on a product requirement because of a technical risk. How did it end?

What they are checking: Whether they can disagree constructively with product partners and land on a decision both sides can live with.

How do you raise the skill level of the engineers on your team without becoming the bottleneck for every design?

What they are checking: Whether they multiply the team's output through mentoring and delegation instead of doing all the hard parts themselves.

What would you do

A restaurant owner wants the cheapest possible schedule, and the staff want predictable shifts. How would you build the product so both sides feel it's fair?

What they are checking: Whether they see the human tradeoffs behind the data model, which is the heart of a scheduling product for employers.

Friday night a scheduling publish job fails for a few hundred restaurants and managers can't send next week's shifts. What do you do first, and what do you do after it's fixed?

What they are checking: Whether they stay calm, protect customers first, and then fix the root cause instead of just the symptom.

If you joined and found the scheduling code had weak test coverage and frequent regressions, how would you improve quality while still shipping roadmap work?

What they are checking: Whether they can make a practical plan to pay down tech debt without stopping delivery or asking for a rewrite.

About the work

Walk me through how you'd design a scheduling engine that builds a labor plan for a restaurant, balancing labor cost, employee availability and forecasted guest demand.

What they are checking: Whether they can model competing constraints as a real system instead of jumping straight to a single optimization trick.

Predictive scheduling laws in some cities require advance notice and pay for last-minute changes. How would you design the system so those rules don't turn into a pile of special cases?

What they are checking: Whether they can make jurisdiction rules configurable and testable rather than hard-coded and fragile.

How do you decide when to break a growing service into smaller services and when to keep it together?

What they are checking: Whether they reason from team ownership and failure boundaries rather than following microservice fashion.

How would you handle shift swaps and time-off requests that happen at the same moment from different devices?

What they are checking: Whether they understand concurrency, conflict resolution and what the user should see when two changes collide.

Practice this interview out loud.

Offer builds a real interview for this exact role at Toast from your resume and this job description, asks the questions one at a time, and tells you what landed. The first one is free.

Practice this out loud

The full job description

As published by Toast.

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. We’re not your traditional tech company and we don’t aim to be. Going against the grain* is in our DNA. Building a revolutionary product begins with revolutionary thinking. That’s why we value diversity of background and lived experience. Together, we empower restaurants of all sizes to build great teams, increase revenue, improve operations, and delight their guests. We pair our deep understanding of the restaurant industry with powerful cloud based software and restaurant-grade hardware to deliver an intuitive all-in-one platform. Join us on our mission to empower the restaurant community to delight guests, do what they love, and thrive.&nbsp; We’re looking for a Staff Software Engineer to join our dynamic Payroll Onboarding team, which supports the Payroll product for Toast restaurants. You’ll play a key roll* in the design, development, and delivery of scalable software solutions that enable restaurant owners to configure Payroll accurately, while empowering internal Toast teams to support go-lives efficiently.. About this roll* (Responsibilities) • Lead deep technical initiatives that improve functionality and reliability for Toast customers • Design solutions that anticipate and accommodate future needs while considering tradeoffs&nbsp; • Participate in architectural discussions and influence the technical roadmap • Collaborate with teams of Design, Product, and other engineering members in developing robust and scalable full-stack software applications • Advocate for best coding practices to raise the bar for you, your team, and the company • Mentor and provide technical guidance, acting as a force multiplier in improving engineering productivity • Leverage cutting-edge AI tools to enhance your development workflow, improve velocity, and help pioneer new approaches to influence what we build and how we build it Do you have the right ingredients*? (Requirements) • 8+ years of back-end experience in Java, Kotlin, or other object-oriented languages • Proven track record of leading technically complex, multi-team projects • Proficient with modern web standards and technologies (e.g. React, TypeScript, REST, GraphQL) • Proficient with traditional databases and alternative data stores • Experience with distributed systems, enterprise messaging systems, and/or microservices • Experience delivering high-quality, reliable services to production • Excellent cross-team communication skills on complex technical topics • Passionate about technology and learning new things 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 $193,000 &mdash; $309,000 USD Zone B $168,000 &mdash; $269,000 USD Zone C $151,000 &mdash; $242,000 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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