Staff Operations AI Engineer

Checkr•Denver, CO

2h•$150,000 - $176,000•Hybrid

About The Position

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.

Requirements

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

Nice To Haves

Direct experience with Tray.io / Make / Zapier / UiPath
Programming experience in Python
Snowflake specifically (vs strong SQL generally)
Salesforce or Zendesk integrations
Front-end UI widgets / embeds
Prior work in operations technology specifically (vs platform, infra, or product engineering)

Responsibilities

AI Agent Integration & Automation Architecture
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.
Systems Engineering & Data Foundations
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.
AI Quality, Safety & Guardrails
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.

Benefits

A fast-paced and collaborative environment
Learning and development allowance
Competitive cash and equity compensation, and opportunity for advancement
100% medical, dental, and vision coverage
Up to $25K reimbursement for fertility, adoption, and parental planning services
Flexible PTO policy
Monthly wellness stipend

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