Principal Software Engineer, Tech Lead, Retail

Posted Yesterday
Hiring Remotely in US
Remote
230K-368K Annually
Expert/Leader
Cloud • Fintech • Food • Information Technology • Software • Hospitality
We empower the restaurant community to delight guests, do what they love, and thrive.
The Role
Design, build, deploy, and maintain resilient, scalable production systems for Toast’s retail customers. The role sets long-term technical architecture and strategy, communicates technical direction, mentors senior engineers, improves engineering productivity, diagnoses performance issues, and drives initiatives amid ambiguity. Engineers collaborate directly with retail customers, visit stores, understand operational workflows, and use AI tools to improve development velocity and quality.
Summary Generated by Built In

Location(s): US (remote), Boston (hybrid), or New York (hybrid)


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  — expect to visit stores and talk directly with operators to deeply understand their workflows. 

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 
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.

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$368,000 USD
Zone B
$200,000$320,000 USD
Zone C
$180,000$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: 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.

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 [email protected].

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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.

Skills Required

  • 9+ years of experience building and shipping production software to customers
  • Experience with Java, Kotlin, or other object-oriented programming languages
  • Humility, empathy, and deep respect for peers
  • Ability to articulate sophisticated project roadmaps and empower engineering cohorts to execute them
  • Startup mindset and ability to create order from ambiguity
  • Passion for making users happy and seeing people use the product in the wild
  • Growth-oriented mindset focused on continuous improvement of craft and domain expertise
  • Ability to establish trusted technical authority and make decisions balancing immediate wins with long-term strategic goals

What the Team is Saying

Christopher
Srishti
JJ
Eden
Jane

Toast Compensation & Benefits Highlights

  • Leave & Time Off Breadth Flexible PTO, paid company holidays, generous paid parental/family/medical leave, and a paid sabbatical after five years are core parts of the package. U.S. materials also highlight a robust time-off baseline as of 2026.
  • Parental & Family Support Sixteen weeks of paid parental leave for all parents with additional weeks for birthing parents, plus fertility and family-forming support (e.g., Carrot), are emphasized. Subsidized backup child and adult care further supports caregivers.
  • Wellbeing & Lifestyle Benefits No‑cost mental‑health therapy/coaching, a wellness stipend, and financial education expand support beyond core insurance. Professional development reimbursement, work‑enablement stipends, and volunteer/donation programs round out lifestyle-oriented offerings.

Toast Insights

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The Company
HQ: Boston, MA
5,000 Employees
Year Founded: 2011

What We Do

Toast is the all-in-one platform built for restaurants of all sizes. Toast provides a single platform of software as a service (SaaS) products and financial technology solutions that give restaurants everything they need to run their business, including point of sale, payments, supplier management, digital ordering and delivery, marketing and loyalty, and team management. By serving as the restaurant operating system across dine-in, takeout, and delivery channels, Toast helps restaurants increase revenue, streamline operations and deliver amazing guest experiences.

Why Work With Us

Our recipe for an awesome workplace: One splash of friendship A dollop of impact A sprinkle of no hierarchy & A heavy spoonful of individuality Mix these ingredients in a fast-paced and hardworking environment. Best paired with a side of interesting people who always bring their whole selves to work. *100% Sunday scary free

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Hybrid Workspace

Employees engage in a combination of remote and on-site work.

Typical time on-site: Flexible
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