Senior Technical R&D Operations Manager

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 def