Senior Technical R&D Operations Manager at 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. Toast R&D is building an AI-native operating layer for how we plan, execute, and learn. This role will help design and build that foundation from the ground up. You will turn messy, manual workflows into structured, automated, and continuously improving systems—leveraging agent-first workflows, integrations, and low-code/no-code builder tools to build standalone applications to solve R&D org-wide problems. Rather than simply administering tools, you will architect how work flows across Jira, JPD, our internal beta testing platform, and adjacent systems—ensuring data integrity, automation by default, and real-time operational insight. This is a builder role: you will identify friction, prototype quickly (often with AI coding tools like Cursor or Claude Code), ship to production, measure impact, and harden what works. This role sits within the R&D Operations team at Toast. We empower teams to build great products efficiently and at scale by removing obstacles, fostering alignment, and equipping teams with the right processes, systems, and insights. A day in the life (Responsibilities) R&D AI Systems Engineering & Automation Optimizing and instrumenting the existing R&D operating system. • Architect automation-first workflows across Jira, JPD, internal beta systems, and adjacent tools. • Design structured data models and guardrails so systems stay clean by default — not through manual enforcement. • Eliminate recurring manual work through event-driven automations and API integrations. • Instrument workflows to generate operational telemetry (cycle time, bottlenecks, throughput). • Build reusable automation patterns that scale beyond one-off fixes. • Treat tool administration as a fallback — system design and automation as the default. AI-Native & Agent-First Systems Help create the AI platform layer that improves how R&D operates. • Design and deploy agent-first workflows where AI systems execute meaningful portions of work autonomously within defined boundaries. • Use AI-native development environments (e.g., Claude Code, Cursor) as daily drivers to prototype and productionize agents and internal AI tools. • Architect multi-step agent systems that retrieve context, reason across structured and unstructured data, generate outputs, and take bounded action. • Establish safe autonomy standards: scoped permissions, observability, evaluation loops, and human escalation paths. • Ship quickly, measure impact, and harden what works. What you'll need to thrive (Requirements) • 8+ years of experience in Technical Operations, Systems Engineering, Product Operations, Platform Engineering, or a similar role within a software or R&D organization. • Demonstrated experience building and shipping AI-native systems & custom tools — including hands-on work with AI coding environments (e.g., Claude Code, Cursor) and agentic workflows. • Experience designing multi-step AI systems that retrieve context, reason, generate outputs, and take bounded action. • Strong systems thinking: ability to design end-to-end workflows across tools, APIs, data models, and automation layers. • Experience integrating systems via APIs and building event-driven automation. • Experience designing human-in-the-loop controls and safe autonomy guardrails. • Strong cross-functional partnership skills and the ability to translate operational friction into production-grade systems. • Clear, concise communicator able to explain technical concepts to both technical and non-technical stakeholders. Preferred Qualifications • Track record of independently identifying operational friction and implementing durable, automation agentic AI-first solutions at scale. • Background operating in a high-growth or high-complexity SaaS environment where systems and governance needed to scale alongside the organization. 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 [Upgrade to PRO to see link] #LI-REMOTE The base salary range for this role is listed below. The starting salary will be determined based on skills and experience. In addition to base salary, our total rewards components include cash compensation (overtime, bonus/commissions, if eligible), benefits, and equity (if eligible). Pay Range$133,000—$213,000 USDHow 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. 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: [Upgrade to PRO to see link] 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 [Upgrade to PRO to see contact]. ------ 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.