Principal Software Engineer

<p>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.</p> <p><strong>A bit about the team</strong></p> <p>Toast Support is undergoing a multi-year transformation to become a seamless, intelligent, and trusted companion for every restaurant—delivering fast, proactive, and deeply human help when it matters most. Support Technology sits at the center of this evolution, powering the tools, platforms, and AI experiences that connect customers, agents, and Toast systems across every support interaction.</p> <p>We are looking for a Principal Software Engineer to help define and drive the technical foundation of this transformation. In this role, you will shape the evolution of Toast’s Support Technology ecosystem, spanning agent tooling, AI-powered voice and chat experiences, the Support Center, customer communication platforms, and a modernization of our omnichannel contact center infrastructure (CCaaS). Your work will directly influence how customers and agents interact across channels – and how those experiences come together as a single, cohesive system.</p> <p>This is a high-impact domain. Support systems must operate reliably under urgent, business-critical conditions; integrate deeply with customer, device, and account data; and scale across millions of interactions while maintaining trust, accuracy, and speed. The platforms you influence will determine how effectively Toast can reduce friction, resolve issues end-to-end, and deliver a differentiated support experience as we grow—modernizing our core support infrastructure through a unified CCaaS foundation and AI-driven capabilities that improve routing, resolution, and outcomes.</p> <p>As a Principal Engineer in Support Technology, you will set technical direction across teams, identify and solve systemic architectural challenges, and raise the bar for quality and execution across the organization. You will partner closely with product, design, data, AI, and operations leaders to build platforms and customer-facing experiences that are extensible, resilient, and easy for other teams to build on—unlocking faster innovation and better outcomes for customers and agents alike.</p> <p>If you’re motivated by large-scale platform transformations, excited to work at the intersection of customer experience, agent experience, and intelligent systems, and eager to leave a lasting mark on how Toast supports restaurants at scale, this role offers a rare opportunity to do so.</p> <p><strong>A day in the life (Responsibilities) </strong></p> <ul> <li>Lead the transformation of our Support Technology architecture, delivering scalable solutions that have significant business impact across customer-facing support experiences and agent tooling.</li> <li>Define and implement frameworks and processes that guarantee the quality, resilience, and scalability of our Support Technology platforms, including our omnichannel contact center (CCaaS), customer-facing Support Center, and customer communications systems.</li> <li>Develop and execute technical strategies to solve complex business challenges, leveraging data-driven decisions to prioritize impactful improvements across voice, chat, and digital support channels.</li> <li>Establish guiding technical and delivery principles that influence engineering practices across the broader engineering organization.</li> <li>Mentor and guide engineers, fostering a culture of continuous improvement, inclusivity, and engineering excellence.</li> <li>Build and maintain strong partnerships across lines of business, aligning technical solutions with strategic objectives.</li> </ul> <p><strong>What you'll need to thrive (Requirements)</strong></p> <ul> <li>8-10 years of experience in software engineering, with a strong background in full-stack development is essential.</li> <li>Extensive experience with Java, Kotlin, or other objec ... (truncated, view full listing at source)