Senior Director, AI Software Engineering

Overview

Diligent is searching for a proactive and technically skilled Director of AI Software Engineering to spearhead and expand AI-related engineering initiatives across multiple business units within Governance, Risk, and Compliance (GRC). This leadership position bridges product delivery, platform advancements, and applied AI to generate tangible improvements in critical workflows.

This role demands a hands-on leader who regularly engages with production coding, oversees complete system deployment, and thrives in ambiguous situations while effectively aligning multiple teams and stakeholders.

Key Responsibilities

• Lead the delivery of AI-enhanced features deeply integrated within business workflows such as risk assessment, automation of compliance, reporting, and due diligence.
• Collaborate closely with product, data, and platform teams to convert business challenges into scalable AI solutions.
• Remain actively involved in architecture design, code reviewing, and implementing essential components.
• Experiment with new AI methodologies including large language models, agents, retrieval systems, and classification pipelines.
• Define and uphold engineering standards to ensure top performance, reliability, and cost effectiveness.
• Lead and nurture a high-performing team comprising AI/ML and software engineers.
• Manage recruitment, provide coaching, and foster career growth for team members.
• Promote a culture emphasizing ownership, agility, and technical excellence.
• Ensure delivery of robust, production-ready systems rather than mere experiments.
• Maintain balanced prioritization and oversight across simultaneous ongoing projects with focus on security, privacy, and compliance.
• Serve as a liaison between engineering groups and business stakeholders to communicate clearly about trade-offs, risks, and deliverables.
• Align cross-functional teams on shared objectives and timelines.

Required Qualifications

• At least 10 years of experience in software engineering, featuring recent practical coding involvement.
• A proven history of launching scalable production software systems.
• Expertise with contemporary AI/ML technologies such as LLMs, natural language processing, search, or significant data platforms.
• Robust backend development skills using languages like Python, Java, or equivalents.
• Experience working with distributed system architectures, APIs, and cloud technologies (AWS, GCP, Azure).
• Knowledge of modern AI infrastructure including vector search, embeddings, model deployment, and agent frameworks.
• Demonstrated leadership quality with the ability to lead engineering teams while staying technically involved and fostering credibility among senior engineers.
• Excellent communication skills enabling simplification of complex technical matters for non-technical stakeholders.
• Capability to operate effectively at both executive and detailed implementation levels.
• Strong bias toward action, thriving in rapidly evolving and unclear environments.
• Focus on generating measurable business outcomes beyond technical accomplishments.

Preferred Experience

• Background in Governance, Risk, and Compliance domains, fintech, or environments subject to regulation.
• Familiarity with FedRAMP or related compliance standards.
• Experience creating AI-driven products instead of purely research-focused AI.

About Diligent

Diligent stands out as a leader in AI-driven SaaS solutions for governance, risk, and compliance, supporting over 1 million users and 700,000 board members worldwide to better understand and manage risk, enhance governance, and improve decision-making processes.

Our vibrant culture is built on creativity, innovation, and continuous learning. We prioritize a flexible workplace, comprehensive health programs, generous leave policies, and foster diversity and inclusion through dedicated resource groups and educational resources.

This position offers hybrid work, expecting onsite presence about half the time for those near company offices, promoting collaboration and community.

Compensation

The salary range for this role spans from 250000 to 310000 CAD annually.

Equal Opportunity and Recruitment Information

Diligent is an equal opportunity employer committed to diversity and non-discrimination in hiring. Reasonable accommodations are provided for applicants with disabilities. The recruitment process involves AI-assisted tools for organizing applications, but final decisions are human-made.

Visa sponsorship may be available depending on role requirements. Recruitment agencies should note that unsolicited resumes are not accepted.