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Salary: USD 150,000 - 176,000 / annual
Checkr is building a data platform to power safe and fair decisions, serving over 140,000 companies and millions of people for AI-driven verification across hiring, housing, transportation, childcare, and dating. The company is recognized on the Forbes Cloud 100 2025 list and is a Y Combinator 2024 Breakthrough Company.
As Staff Operations AI Engineer, you will architect, build, and refine the intelligent systems powering Checkr's AI-driven operations. You'll be the technical expert responsible for designing 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.
Key responsibilities include:
**AI Agent Integration & Automation Architecture:** Design and own the integration architecture enabling 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 coordinating 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, leading technical solutions that improve reliability and scale.
**Systems Engineering & Data Foundations:** Build and maintain technical foundations powering AI-driven workflows, including structured data pipelines, normalized schemas, and predictable JSON inputs for LLMs. Establish engineering standards for workflow design, code quality, and system observability. Communicate architecture clearly through documentation and diagrams, serving as a technical authority across teams to ensure consistent, high-quality execution.
**AI Quality, Safety & Guardrails:** Implement guardrails, validation rules, and safety checks ensuring 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.
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.
**Requirements:**
- 5-7+ years in 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 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, with proven 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 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
- A-player mindset with strong bias for action: raise the bar, move with urgency, stay resilient through ambiguity, take ownership to deliver meaningful outcomes
**Nice-to-Have:** Direct experience with Tray.io, Make, Zapier, or UiPath; Snowflake specifically; Salesforce or Zendesk integrations; front-end UI widgets/embeds; prior work in operations technology.
