Staff Operations AI Engineer, Checkr

• 7+ years in systems engineering, automation platforms, integration architecture, or AI-enabled operations
• Deep expertise in API design, OAuth/token-based authentication, webhooks, and event-driven systems
• Proven experience building reliable automation workflows with observability, retries, and failure handling
• Strong JavaScript and/or Python expertise for backend logic, scripting, and internal tooling
• Solid SQL experience for data transformation, validation, and operational analytics (Snowflake a plus)
• 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

Desirable

• 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
• 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
• Proactively identify integration gaps, system bottlenecks, and failure modes, and lead the technical solutions that improve reliability and scale
• Build and maintain the technical foundations that power AI-driven workflows, including structured data pipelines, normalized schemas, and predictable JSON inputs for LLMs
• Write high-quality JavaScript and SQL to support automation logic, internal tooling, and operational insights
• Establish engineering standards for workflow design, 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 and accurately in production
• Evaluate model output quality and continuously refine prompts, transformations, and logic to improve consistency, reliability, and trust in AI-driven decisions