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 and 

What Diligent Offers You  

• Creativity is ingrained in our culture. We are innovative collaborators by nature. We thrive in exploring how things can be differently both in our internal processes and to help our clients
• We care about our people.  Diligent offers a flexible work environment, global days of service, comprehensive health benefits, meeting free days, generous time off policy and wellness programs to name a few
• We have teams all over the world . We may be headquartered in New York City, but we have office hubs in Washington D.C., Vancouver, London, Galway, Budapest, Munich, Bengaluru, Singapore, and Sydney.
• Diversity is important to us. Growing, maintaining and promoting a diverse team is a top priority for us. We foster and encourage diversity through our Employee Resource Groups and provide access to resources and education to support the education of our team, facilitate dialogue, and foster understanding.

Diligent created the modern governance movement. Our world-changing idea is to empower leaders with the technology, insights and connections they need to drive greater impact and accountability – to lead with purpose. Our employees are passionate, smart, and creative people who not only want to help build the software company of the future, but who want to make the world a more sustainable, equitable and better place. 

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.

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 Diligent's 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 View email address on job-boards.greenhouse.io .

At Diligent, we recognize the value of a diverse global workforce. Visa sponsorship may be available for select positions based on business needs and specific role requirements. Sponsorship decisions are evaluated on a case-by-case basis, and eligibility should not be assumed for all opportunities.

Please find the link to our candidate privacy policy here:  

To all recruitment agencies: Diligent does not accept unsolicited agency resumes. Please do not forward resumes to our jobs alias, Diligent employees or any other organization location. Diligent is not responsible for any fees related to unsolicited resumes.