Director, AI Software Engineering

Role overview

Diligent is hiring a hands-on Director of AI Software Engineering to guide and expand AI engineering work across several business units in governance, risk, and compliance (GRC). The position blends product delivery, platform growth, and applied AI to create measurable improvements in key business workflows.

This is a builder-first leadership role rather than a pure people-management position. The team is looking for someone who has recently contributed production code, launched systems end to end, and is comfortable navigating ambiguity while bringing teams and stakeholders into alignment.

Key responsibilities

You will own delivery of AI-driven features embedded in business workflows such as risk analysis, compliance automation, reporting, and due diligence. You will work closely with product, data, and platform teams to turn business problems into scalable AI systems.

The role also requires active technical involvement, including architecture work, code reviews, and implementation on critical paths, along with experimentation and validation of newer approaches such as LLMs, agents, retrieval systems, and classification pipelines. You will help define engineering practices that improve performance, reliability, and cost efficiency.

In addition, you will lead and mentor a strong team of AI/ML and software engineers, support hiring and coaching, and build a culture centered on ownership, speed, and technical excellence. You will be expected to ship production systems, not proof-of-concept experiments, while balancing delivery speed with security, privacy, and compliance requirements.

The position also involves strong cross-functional communication. You will connect engineering and business stakeholders, explain trade-offs and risks clearly to senior leaders, and keep multiple initiatives moving with clear prioritization and shared timelines.

What the company is looking for

The ideal candidate brings more than 10 years of software engineering experience, including recent hands-on coding. You should have a track record of launching production systems at scale and experience with modern AI/ML technologies such as LLMs, NLP, search, or data platforms.

Strong backend development ability is important, with experience in languages such as Python, Java, or similar. You should also be familiar with distributed systems, APIs, and cloud environments such as AWS, GCP, or Azure, plus modern AI infrastructure including vector search, embeddings, model serving, and agent frameworks.

The role requires a leader who can stay technically involved while managing engineers, earn credibility with senior technical talent, and challenge ideas constructively. You should also be able to simplify complex technical concepts for non-technical audiences and operate effectively at both executive and implementation levels.

Success in this role depends on a bias toward action, comfort working in fast-changing and ambiguous settings, and a focus on measurable business outcomes rather than technical output alone.

Nice to have

Additional value will be given to candidates with experience in GRC, fintech, or regulated environments, exposure to FedRAMP or comparable compliance frameworks, and a background in building AI-powered products rather than only research-oriented work.

Why this opportunity stands out

This role offers direct influence over how AI reshapes core GRC workflows, the chance to define and scale AI-native systems across the platform, high visibility with senior leadership and business stakeholders, and the opportunity to build real customer-facing products rather than internal experiments.

Compensation

The stated pay range for this role is CAD 200,000 to CAD 240,000 per year.

About Diligent

Diligent is a governance, risk, and compliance SaaS company focused on helping more than 1 million users and 700,000 board members better understand risk, strengthen governance, and make faster decisions. Its platform provides a unified view of GRC activities for practitioners, executives, and boards.

The company describes itself as fast-moving and innovation-driven, with teams working on large language model applications and AI-enabled workflow redesign. It values curiosity, experimentation, continuous learning, and work that creates positive change.

Work model and locations

Although headquartered in New York, Diligent operates office hubs in Washington D.C., Vancouver, London, Galway, Budapest, Munich, Bengaluru, Singapore, and Sydney. This position follows a hybrid arrangement. If you live within commuting distance of a Diligent office, you are expected to be onsite at least 50% of the time.

Benefits and culture

• Innovative, collaborative culture that encourages creative thinking and new ways of working
• Flexible work environment
• Global days of service
• Comprehensive health coverage
• Meeting-free days
• Generous paid time off
• Wellness programs
• Commitment to diversity, supported by employee resource groups, learning resources, and open dialogue

Additional information

Diligent states that it is a drug-free workplace and an equal opportunity employer. Hiring decisions are made without discrimination based on protected characteristics, and qualified applicants are considered regardless of criminal history where permitted by law.

The company also says it will provide reasonable accommodations in the application process for qualified individuals with disabilities and disabled veterans. Recruitment agencies are asked not to submit unsolicited resumes, as such submissions will not be accepted and fees will not be paid for them.