Staff Operations AI Engineer

About Checkr
Checkr is building the data platform to power safe and fair decisions. Established in 2014 Checkrs innovative technology and robust data platform help customers assess risk and ensure safety and compliance to build trusted workplaces and communities. Checkr has over 100000 customers including DoorDash Coinbase Lyft Instacart and Airtable.

Were a team that thrives on solving complex problems with innovative solutions that advance our mission. Checkr is recognized on Forbes CloudList and is a Y Combinator 2024 Breakthrough Company.

About the Role

Were looking for a Staff Operations AI Engineer who will architect build and refine the intelligent systems that power Checkrs AI-driven this role youll be the technical expert responsible for designing the integrations workflows and data structures that enable AI Agents and automation to operate reliably at scale.

Youll work across system integration workflow orchestration application logic data transformation AI guardrails and multi-platform automationtranslating leaderships strategic direction into high-quality technical execution. Youll 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.

What Youll Own

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.

What You Bring

Required Experience

• 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)

Systems & Architecture

• 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

Mindset & Leadership

• 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 Checkrs values; mentors others and contributes to a healthy inclusive team culture

Nice-to-Have Experience

• Direct experience with / 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)

What youll get

• 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

#TD-LI1

At Checkr we believe a hybrid work environment strengthens collaboration drives innovation and encourages connection. Our hub locations are Denver CO San Francisco CA Nashville TN and Santiago Chile. Individuals are expected to work from the office 3 days a -office perks are provided such as lunch five times a week a commuter stipend and an abundance of snacks and beverages. A relocation stipend may be available for those willing to relocate to a Checkr hub location.

Equal Employment Opportunities at Checkr
Checkr is committed to building the best product and company which requires hiring talented and qualified individuals with a diverse set of perspectives and lived experiences. Checkr believes in hiring people of all backgrounds including those whose histories are impacted by the justice system in accordance with local state and/or federal laws including the San Franciscos Fair Chance Ordinance.

Applicant Privacy Policy
If you are a California resident or are located in Alberta or British Columbia our Applicant Privacy Policy applies to our collection and processing of your personal information when you apply for a role with us or otherwise participate in our recruitment process.

*Legitimate Checkr emails will always include our official domain name after the @ symbol (e.g. or ).