Senior Director, AI Software Engineering

Overview 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 Lead AI Engineering Across GRC 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 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 $250,000 — $310,000 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.