OverviewWe are seeking a hands-on Director of AI Software Engineering to lead and scale AI engineering efforts supporting multiple business units across Governance, Risk, and Compliance (GRC). This role sits at the intersection of product delivery, platform evolution, and applied AI-driving real-world impact across core workflows.
This is not a pure management role. We are looking for a builder who leads from the front, someone who has recently written production code, shipped systems end-to-end, and can operate comfortably in ambiguity while aligning teams and stakeholders.
What You'll DoLead AI Engineering Across GRCOwn delivery of AI-powered capabilities embedded directly into business unit workflows (e.g., risk analysis, compliance automation, reporting, due diligence)
Partner with product, data, and platform teams to translate business problems into scalable AI systems
Stay Hands-On- Contribute to architecture, code reviews, and critical path implementation
- Prototype and validate new approaches (LLMs, agents, retrieval systems, classification pipelines, etc.)
- Set engineering standards for performance, reliability, and cost efficiency
Build and Scale Teams- Lead and mentor a high-performing team of AI/ML and software engineers
- Drive hiring, coaching, and career development
- Establish a culture of ownership, speed, and technical excellence
Drive Execution- Deliver production-grade systems-not experiments
- Balance speed with rigor (security, privacy, compliance)
- Operate across multiple concurrent initiatives with clear prioritization
Communicate and Influence- Act as a bridge between engineering and business stakeholders
- Clearly articulate trade-offs, risks, and outcomes to senior leadership
- Align cross-functional teams around shared goals and timelines
What We're Looking ForProven Builder- 10+ years in software engineering, with recent hands-on coding experience
- Demonstrated track record of shipping production systems at scale
- Experience with modern AI/ML systems (LLMs, NLP, search, or data platforms)
Technical Depth- Strong backend engineering skills (e.g., Python, Java, or similar)
- Experience with distributed systems, APIs, and cloud platforms (AWS/GCP/Azure)
- Familiarity with modern AI stacks (e.g., vector search, embeddings, model serving, agent frameworks)
Leadership with Credibility- Experience leading engineering teams while remaining technically engaged
- Ability to earn trust with senior engineers and challenge them constructively
Strong Communicator- Can simplify complex technical concepts for non-technical stakeholders
- Comfortable operating at both executive and implementation levels
Execution-Oriented- Bias for action; thrives in fast-moving, ambiguous environments
- Focused on delivering measurable business impact-not just technical output
Nice to Have- Experience in GRC, fintech, or regulated environments
- Exposure to FedRAMP or similar compliance frameworks
- Background in building AI-powered products (not just research)
Why This Role- Direct influence on how AI transforms core GRC workflows
- Opportunity to define and scale AI-native systems across the platform
- High visibility with senior leadership and business stakeholders
- Build real products used by customers, not internal experiments
Pay Range
$200,000-$240,000 CAD
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.
