We 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 Do

Own 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 For

Proven 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

• 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


• 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


• Prospect 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

$173,920 - $217,400 CAD

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 Diligents 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 [email protected].