Senior Software Engineer, Support AI at Toast in Remote

About Toast: Toast is driven by building the restaurant platform that helps restaurants adapt, take control, and get back to what they do best: building the businesses they love. Are you bready* for a change? (Team Info) The Support AI team is building voice and chat systems that handle customer support at scale—helping restaurants resolve issues quickly, often before they ever reach a human. This is high-impact, real-world AI. When these systems work well, customers get unblocked instantly. When they don’t, it directly affects a restaurant’s ability to operate. Accuracy, speed, and reliability aren’t nice-to-haves—they’re critical. We’re early in building these capabilities. Voice AI is launching, chat AI is improving, and we’re learning what actually drives better outcomes as we go. Many of the right answers haven’t been figured out yet. You’ll work in an environment where shipping fast, learning from real interactions, and building systems that scale all have to happen at once. You’ll put things into production to see what works, measure real customer outcomes, and iterate quickly—making pragmatic calls about when to move fast and when to invest for the long term. As a Senior Software Engineer on Support AI, you’ll drive projects end-to-end: building and evolving voice and chat systems, improving integrations based on production data, and scaling platforms that handle millions of customer interactions. You’ll work closely with product, support operations, and AI engineering teams to turn ambiguous problems into systems that actually help customers. You’ll navigate integration constraints, messy data, and competing priorities while the platform—and the problem space—continue to evolve. If you’re motivated by building AI systems that work in the real world and want to see your work directly improve how restaurants get help when they need it most, this is a role where you can have immediate, visible impact. About this roll* (Responsibilities) Drive end-to-end development of voice and chat AI systems—from concept through production—owning the full lifecycle and iterating based on real customer and operational outcomes. Build and evolve integrations with third-party AI platforms and internal Toast systems, making pragmatic decisions that balance speed, reliability, and long-term scalability. Design and implement observability, monitoring, and outcome tracking for AI-powered support experiences—using production data to understand system performance and continuously improve customer outcomes. Make technical decisions grounded in production data, customer feedback, and operational constraints—navigating ambiguity while building systems that scale. Partner closely with product, support operations, and AI/ML engineering teams to translate ambiguous problems and workflows into robust, maintainable systems that drive measurable impact. Contribute to technical design and architecture discussions, helping shape system design, tradeoffs, and engineering standards. Mentor and support other engineers through code reviews, pairing, and technical guidance, fostering a culture of ownership, quality, and continuous improvement. Do you have the right ingredients*? 5+ years of experience in software engineering, with a strong background building and maintaining production systems using Java, Kotlin, or other object-oriented languages. Proven ability to own complex features or projects end-to-end, from design through production and iteration. Experience building integrations with third-party APIs or platforms, especially in domains where reliability, latency, and vendor constraints matter. Comfortable working in ambiguity and making pragmatic tradeoffs between shipping quickly and building for scale Strong collaborator who can work effectively across product, operations, and technical teams to deliver customer and business outcomes. Proficient with AI tooling such as Cursor, Claude, and MCP servers Self-starter who takes ownership of problems, unblocks themselves, and drives work forward without waiting for perfect conditions. 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 $159,000—$254,000 USD Zone B $138,000—$221,000 USD Zone C $125,000—$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. To learn more: https://careers.toasttab.com/ai-in-hiring Diversity, Equity, and Inclusion is Baked into our Recipe for Success At Toast, our employees are our secret ingredient—when they thrive, we thrive. The restaurant industry is one of the most diverse, and we embrace that diversity with authenticity, inclusivity, respect, and humility. By embedding these principles into our culture and design, we create equitable opportunities for all and raise the bar in delivering exceptional experiences. 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 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.