AI Systems & Data Engineer

About the Role Diligent is the AI leader in GRC solutions, helping organizations around the world turn governance, risk, compliance, audit, and ESG into a competitive advantage. Within HR we're embarking on our own transformation journey to fundamentally redesign how our people experience HR at Diligent. We're looking for a AI Systems & Data Engineer who can co-own the technical heavy lifting of this transformation. This isn't just configuration work — you'll write Python scripts for complex data conversions, build AI agents and standalone people-facing solutions, architect integrations, design automation workflows, and solve problems we haven't encountered yet. We need a strong engineer who can figure things out, move fast, and think about the impact on thousands of people, not just data rows—someone who cares about impact, not just technically elegant solutions. You'll have the autonomy to propose ideas, experiment, and own outcomes, while working with experienced HR and technology teams who can provide context and support. Key Responsibilities Play a key role in the data migration workstream from Oracle HCM and Greenhouse to Workday — writing Python scripts for complex data transformations, conducting manual data audits to validate integrity, and building automated validation frameworks. Design and build a modern AI-powered automated acceptance testing framework for the Workday implementation — enabling the team to run rigorous, repeatable UAT without manual overhead. Design and build scalable workflow automations across the HR tech stack, using Workato and other platforms. Build conversational AI agents and standalone AI-powered solutions (e.g. self-service People Experience tools) on DiligentGPT (Glean), Workato, self-hosted, and other platforms — including hosted tools with their own presence beyond a single chat interface. Build AI-powered auditing and validation agents to monitor data integrity, flag anomalies, and surface quality issues across HR systems — with AI layer exploration. Support implementation and configuration of HR tooling and integrations across the tech stack, ensuring systems are properly connected and maintained. Create data visualisations and dashboards that enable HR stakeholders to access insights, make data-driven decisions, and identify opportunities for automation — while also monitoring migration progress and system health. Document technical architecture, data flows, and integration patterns to enable future maintenance and support knowledge transfer. Troubleshoot and resolve data quality issues, integration failures, and system errors as they arise during implementation and post-go-live. Partner with HR Operations, HRIS, and business stakeholders to gather technical requirements and translate business needs into technical solutions. Question assumptions, propose better approaches, and advocate for solutions that are technically sound and human-centred. Required Skills & Experience 4+ years of hands-on engineering experience building data pipelines, integrations, or automation systems Strong Python skills with experience in complex data transformations and clean, maintainable code Experience with APIs (REST, SOAP), JSON, XML and integrating different systems; comfortable with SQL and database concepts Experience with automation/integration platforms (e.g. Workato, JSM) and AI agents, chatbots, or LLM-powered applications Familiarity with enterprise HRIS platforms (Workday, Oracle HCM) and understanding of HR data structures Proven track record of leading technical projects end-to-end with stakeholder management and delivery ownership Self-directed and outcome-focused — you figure things out, communicate technical concepts clearly, and care about solving problems What You'll Gain Understanding of how HR transformation works at scale across a global organization. Deep hands-on experience with Workday (industry-leading HRIS) implementation and configuration AI agent development and LLM integrati