Diligent is looking for a Technical Director of Data Engineering to help design and build the next generation of data and AI infrastructure powering our products and internal platforms.

This is not a traditional management role. We are looking for an experienced builder; someone who still enjoys writing code, debugging distributed systems, evaluating frameworks, and getting hands-on with architecture and implementation.

You will work across large-scale ingestion pipelines, search systems, AI/LLM infrastructure, event-driven architectures, vector databases, analytics platforms, and real-time data processing. You should be equally comfortable discussing high-level architecture with senior leadership and diving into a failing Kubernetes pod or optimizing a Spark job.

The ideal candidate has strong opinions informed by real-world experience, understands tradeoffs deeply, and can move quickly without creating unnecessary complexity.

What You’ll Do

Design and build scalable data platforms and distributed processing systems
Develop modern ingestion, transformation, and retrieval pipelines for structured and unstructured data
Build systems supporting AI/LLM applications, semantic search, RAG pipelines, vector search, and agentic workflows
Work hands-on with engineering teams to implement production-grade solutions rather than producing slideware
Evaluate and standardize frameworks, tooling, and infrastructure patterns across teams
Improve performance, reliability, observability, and cost efficiency of data systems
Partner with product and platform engineering teams to accelerate delivery of AI-native capabilities
Drive pragmatic engineering decisions balancing speed, maintainability, and operational simplicity
Mentor engineers technically through design reviews, architecture guidance, and pair debugging
Help establish engineering standards around CI/CD, testing, data quality, monitoring, and operational excellence

What We’re Looking For

Strong Hands-On Engineering Experience

Candidates should have significant real-world experience building and operating production systems using many of the following:

Data & Distributed Systems

Airflow
Elasticsearch / OpenSearch
Vector databases and semantic retrieval systems
MongoDB, PostgreSQL, DynamoDB, or similar platforms

Cloud & Infrastructure

AWS
AWS CDK
Serverless architectures
Distributed observability and monitoring stacks

AI / Search / Modern Data Applications

LLM integration patterns
RAG architectures
Embeddings and vector search
MCP servers and AI orchestration frameworks
LangChain, LlamaIndex, DSPy, or similar ecosystems
AI evaluation, tracing, and observability tooling
Search relevance and ranking systems

Backend Engineering

Python strongly preferred
Experience with Java, Go, or TypeScript is a plus
API design and distributed service architectures
Event-driven and asynchronous systems

The Right Candidate

Still enjoys building and debugging systems directly
Has strong technical depth, not just architectural vocabulary
Comfortable operating in ambiguity and fast-moving environments
Understands how to simplify systems instead of endlessly abstracting them
Has experience modernizing legacy platforms and evolving architectures incrementally
Can distinguish between engineering fundamentals and hype cycles
Values shipping working systems over theoretical perfection

What Success Looks Like

Engineering teams can move faster because the underlying platforms are reliable and scalable
AI and data systems become production-grade rather than experimental prototypes
Infrastructure costs and operational complexity are reduced through better architecture
Search, ingestion, and retrieval systems improve significantly in performance and relevance
Teams adopt consistent, maintainable technical patterns without excessive bureaucracy

Nice to Have

Experience with large-scale news, document, or regulatory data pipelines
Experience with search relevancy tuning and semantic retrieval
Exposure to governance, compliance, risk, or enterprise SaaS platforms
Familiarity with modern AI engineering workflows and agentic systems
Experience supporting both startup-speed execution and enterprise-scale operations

Pay Range

$180,000—$210,000 CAD

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.}

Technical Director, Data Engineering