Operations AI Engineer

About Checkr Checkr is building the data platform to power safe and fair decisions. Established in 2014, Checkr’s innovative technology and robust data platform help customers assess risk and ensure safety and compliance to build trusted lern workplaces and communities. Checkr has over 100,000 customers including Door Dash, Coinbase, Lyft, Instacart, and Airtable. We’re a team that thrives on solving complex problems with innovative solutions that advance our mission.

Checkr is recognized on Forbes Cloud 100 2025 List and is a Y Combinator 2024 Breakthrough Company.

We’re looking for a Staff Operations AI Engineer who will architect, build, and refine the intelligent systems that power Checkr’s AI‑driven operations. In this role, you’ll be the technical expert responsible for designing the integrations, workflows, and data structures that enable AI Agents and automation to operate reliably at scale აც them.

You’ll work across system integration, workflow orchestration, application logic, data transformation, AI guardrails, and multi‑platform automation—translating leadership’s strategic direction into high‑quality technical execution. You’ll own complex, high‑impact projects end‑to‑end, serve as a technical authority across teams, and develop robust systems that materially improve operational efficiency and AI performance.

• Design and own the integration architecture that enables AI Agents to operate safely and reliably across Checkr systems and third‑party platforms.
• Build production‑grade API integrations with secure authentication flows, webhook and event‑driven patterns, and robust automation workflows that coordinate actions across tools like Zendesk, Salesforce, and internal services.
• Ensure AI‑driven operations are resilient through strong error handling, retries, observability, and fallback mechanisms.

• Build and maintain the technical foundations that power AI‑driven workflows, including structured data pipelines, normalized schemas, and predictable JSON inputs for LLMs.
• Establish engineering standards for workflow design اجل code quality and system observability.
• Communicate architecture clearly through documentation and diagrams, and serve as a technical authority across teams to ensure consistent, high‑quality execution.

• Implement guardrails, validation rules, and safety checks that ensure AI Agents act responsibly và accurately in production.
• Evaluate model output quality and continuously refine prompts, transformations, and logic to improve consistency, reliability, and trust in AI‑driven decisions.

Required Experience

• 7+ years in systems engineering, automation platforms, integration architecture, or AI‑enabled operations
• Deep expertise in API design, OAuth/token‑based ډېر authentication, webhooks, and event‑driven systems
• Proven experience building reliable automation workflows with observability, retries, and failure handling
• Advanced comfort with JSON, schemas, and data normalization for LLM and automation use cases
• Hands‑on experience running LLM‑powered agents or automations in production, including guardrails and output validation
• Formal experience in prompt engineering frameworks
• Familiarity with integrating with CRM and support systems (e.g., Salesforce, Zendesk)
• Track record designing end‑to‑end integration architectures across multiple platforms
• Ability to translate complex operational needs into scalable, maintainable technical systems
• Experience in anticipating API changes, schema drift, and downstream impacts in production environments
• Systems thinker who understands how data, automation, and AI interact across the stack
• Strong sense of ownership and commitment to building reliable, testable, observable systems
• High bar for engineering rigor, with sound judgment around AI safety, governance, and compliance
• Clear communicator who collaborates effectively across technical and non‑technical partners
• Role model of Checkr’s values; mentors others and contributes to a healthy, inclusive team culture

Nice‑to‑Have Experience

• Direct experience with Tray.io / Make / Zapier / Ui Path
• Programming…