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 integration experience building production tools used by thousands of employees
- Enterprise data migration and integration architecture expertise across complex HR systems
- Automation platform mastery and workflow design skills
- Exposure to the intersection of people, process, technology, and change management while building relationships across HR, IT, Data, and Apps teams
- Portfolio-worthy work: AI agents, data pipelines, and integrations used by 2,500+ employees across 21 countries
- Experience that translates to HR tech consulting, product engineering, or senior IC/leadership roles
This is a one year fixed-term role (possibility to move to permanent) tied to our Workday implementation and AI transformation roadmap. You'll report to the Senior Director of HR AI & Systems Transformation (who is based in London) and work closely with our global team across HR Operations, HRIS, IT, Data, Apps, and transformation project teams.
#LI-Hybrid
About Us
Diligent is the AI leader in governance, risk and compliance (GRC) SaaS solutions, helping more than 1 million users and 700,000 board members to clarify risk and elevate governance. The Diligent One Platform gives practitioners, the C-Suite and the board a consolidated view of their entire GRC practice so they can more effectively manage risk, build greater resilience and make better decisions, faster.
At Diligent, we're building the future with people who think boldly and move fast. Whether you're designing systems that leverage large language models or part of a team reimaging workflows with AI, you'll help us unlock entirely new ways of working and thinking. Curiosity is in our DNA, we look for individuals willing to ask the big questions and experiment fearlessly - those who embrace change not as a challenge, but as an opportunity. The future belongs to those who keep learning, and we are building it together. At Diligent, you’re not just building the future - you’re an agent of positive change, joining a global community on a mission to make an impact.
Learn more at diligent.com or follow us on LinkedIn and Facebook
What Diligent Offers You
- Creativity is ingrained in our culture. We are innovative collaborators by nature. We thrive in exploring how things can be differently both in our internal processes and to help our clients
- We care about our people. Diligent offers a flexible work environment, global days of service, comprehensive health benefits, meeting free days, generous time off policy and wellness programs to name a few
- We have teams all over the world. We may be headquartered in New York City, but we have office hubs in Washington D.C., Vancouver, London, Galway, Budapest, Munich, Bengaluru, Singapore, and Sydney.
- Diversity is important to us. Growing, maintaining and promoting a diverse team is a top priority for us. We foster and encourage diversity through our Employee Resource Groups and provide access to resources and education to support the education of our team, facilitate dialogue, and foster understanding.
Diligent created the modern governance movement. Our world-changing idea is to empower leaders with the technology, insights and connections they need to drive greater impact and accountability – to lead with purpose. Our employees are passionate, smart, and creative people who not only want to help build the software company of the future, but who want to make the world a more sustainable, equitable and better place.
Headquartered in New York, Diligent has offices in Washington D.C., London, Galway, Budapest, Vancouver, Bengaluru, Munich, Singapore and Sydney. To foster strong collaboration and connection, this role will follow a hybrid work model. If you are within a commuting distance to one of our Diligent office locations, you will be expected to work onsite at least 50% of the time. We believe that in-person engagement helps drive innovation, teamwork, and a strong sense of community.
We are a drug free workplace. Diligent is proud to be an equal opportunity employer. We do not discriminate based on race, color, religious creed, sex, national origin, ancestry, citizenship status, pregnancy, childbirth, physical disability, mental disability, age, military status, protected veteran status, marital status, registered domestic partner or civil union status, gender (including sex stereotyping and gender identity or expression), medical condition (including, but not limited to, cancer related or HIV/AIDS related), genetic information, or sexual orientation in accordance with applicable federal, state and local laws. We also consider qualified applicants regardless of criminal histories, consistent with legal requirements. See also Diligent's EEO Policy and Know Your Rights. We are committed to providing reasonable accommodations for qualified individuals with disabilities and disabled veterans in our job application procedures. If you need assistance or an accommodation due to a disability, you may contact us at recruitment@diligent.com.
To all recruitment agencies: Diligent does not accept unsolicited agency resumes. Please do not forward resumes to our jobs alias, Diligent employees or any other organization location. Diligent is not responsible for any fees related to unsolicited resumes.
