Principal Software Engineer, Toast
Full relocation provided
Point of sale and management system for restaurants
Be an early applicant
Point of sale and management system for restaurants
1001+ employees
Be an early applicant
Full relocation provided
1001+ employees
Company mission
Toast's mission is to enrich the food experience for all.
Role
Who you are
- 10+ years of experience designing and delivering scalable software systems, with a strong full-stack background spanning backend services and frontend or developer-facing interfaces
- Demonstrated experience leading technical architecture for a platform, product, or engineering team
- Experience building, deploying, or operating LLM-powered agents or AI platform infrastructure
- Familiarity with AI coding assistants (e.g., Claude Code, Cursor, GitHub Copilot) and experience extending them through custom plugins, skills, or hooks
- Experience with MCP (Model Context Protocol), tool use patterns, or similar agentic integration frameworks
- Strong prompt engineering skills and intuition for how LLM behavior responds to context and instructions
- Strong foundation in modern backend (Java, Kotlin, or similar) and frontend (TypeScript, React, or similar) technologies
- A bias towards action and comfort operating in ambiguous, rapidly evolving problem spaces
Desirable
- Familiarity with A2A (Agent-to-Agent) protocols and multi-agent orchestration patterns
- Experience with machine learning concepts, model evaluation, or ML infrastructure
- Experience building developer experience platforms or internal tooling
- Familiarity with observability tooling for AI/LLM systems (e.g., Langfuse, DataDog)
What the job involves
- As a Principal Software Engineer, you'll work full-stack across ambitious, cross-cutting initiatives, bringing deep technical expertise and architectural judgment to some of the hardest problems at Toast
- Lead full-stack design and delivery of AI-native solutions that address complex, cross-functional problems across Toast
- Drive technical architecture for pod initiatives, from backend services and APIs to frontend and developer-facing interfaces
- Build and integrate LLM-powered agents, tools, and workflows that bring AI capabilities directly into product and platform contexts
- Set and uphold engineering standards within the pod: code quality, system design, testing, and operational practices
- Mentor engineers through design reviews, code reviews, and pairing
- Partner with stakeholders across Toast engineering to define problem scope, align on approach, and deliver outcomes
- Serve as a technical voice in cross-team architecture discussions, connecting pod work to broader Toast engineering patterns
Our take
Running a restaurant means managing a stressful set of elements, all needing to work together seamlessly to create a good experience for diners. Toast helps to streamline processes, and puts an end to piles of paperwork, by providing a platform whereby tableside ordering, menu modifications, labour management, payroll, and more are all housed in one system that can run from a tablet.
Toast offers restaurant-grade hardware and cloud-based, customisable payment solutions to serve clients from startup through to growth phase, as well as a service for established restaurants. By combining all the digital services a restaurant might need, the platform can act as the one and comprehensive solution for restaurants of any size, avoiding restaurateurs from having to invest in a range of technologies.
Toast has over 70,000 restaurants on its books, from food trucks to national brands, and its mobile ordering and payment solutions have made it a recognized brand for consumers. The company's IPO in 2021 saw it valued at over $30 billion and since then, it has added more features to its product suite including wholesale and catering order tools. Toast then, has proven its place as an indispensable player in the restaurant space.
Freddie
Company Specialist at Welcome to the Jungle
Insights
28% employee growth in 12 months
Company
Funding (last 2 of 6 rounds)
Feb 2020
$400m
SERIES F
Apr 2019
$250m
SERIES E
Total funding: $899m
Company benefits
- Peer and company recognition programs
- Unlimited Vacation
- Sabbatical opportunity after five years
- Professional Development Reimbursement Program
- Commitment to Employee Wellness through resources such as a quarterly Wellness Stipend
- Various peer and company recognition programs
- 401(k) and matching
- Medical, Dental, & Vision Coverage
- Mental Health Benefits
- Subsidized backup childcare
Company HQ
Fort Point Channel Landmark District, Boston, MA
Leadership
Steve Fredette
(Co-Founder & President)They studied at MIT before co-founding Klick Mobile in 2009 and spending almost 7 years at Endeca. They left their Management role in June 2012 having co-founded Toast in May.
Aman Narang
(Co-Founder & CEO)Having studied Computer Science at MIT, they worked at Endeca for 5 years. They moved from working as Product Manager to work full-time as President of Toast in 2013, having co-founded it the previous year.
Jonathan Grimm
(Co-Founder & CTO)They also studied Computer Science at MIT before working as an Engineer for Endeca for over 4 years. They worked at Oracle for 5 months prior to co-founding Toast in May 2012.
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