Senior Director, AI Software Engineering
Diligent CorporationVancouver, British Columbia, Canada · Posted 4 months agoDescription
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
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.
Learn more at diligent.com or follow us on LinkedIn and Facebook
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.
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 US EEOC’s Know Your Rights. We are a drug free workplace.
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 recruitment@diligent.com.
Similar jobs
Diligent is looking for a Technical Director of Data Engineering to help design and build the next generation of data and AI infrastructure powering our products and internal platforms. This is not a traditional manageme…
This position is based in Vancouver, BC, within Diligent’s Technical Center of Excellence. We are currently hiring candidates who are based in or able to work from Vancouver. Software Engineer — Platform AI Service Level…
Here’s a summary of the role: Lead a strong engineering team, deliver software that matters, and help people do the best work of their careers. This is a hands-on team management role for someone who enjoys combining peo…
Est. 80,000 EUR
Position Overview As a Software Engineer at Diligent, you’ll be hands-on in building and improving the services that power our SaaS platform. You’ll work on designing, developing, and maintaining secure and scalable micr…
Here’s a summary of the role: Diligent is seeking for an Advisory Specialist I (Entities) to join our growing Professional Services team. We're looking for individuals who are passionate about technology and consistently…
Position Overview: The Services team has unrivalled expertise across corporate governance, audit, risk, compliance, and regulatory environments in many sectors. They have the scale and reach to deliver significant change…
Est. 84,000 EUR
Here’s a summary of the role: As a Senior Software Engineer at Diligent, you’ll be hands-on in shaping the future of our Compliance Products by designing and delivering secure, scalable, and high-performing services that…
Est. 111,640 USD
Position Overview Diligent is looking for an experienced GRC Advisor to join the team and work on Key accounts to drive adoption and retention and identify areas for expansion within our platform. This position will leve…
Est. 84,000 EUR
Here’s a summary of the role: Imagine owning features from user interface to cloud infrastructure, working on Diligent's flagship product, and helping build technology used by some of the world's most influential organiz…
Platform administration isn't the part of the product anyone screenshots for a demo. Nobody's writing a blog post about your identity provisioning flow. But it's the thing every other team at Diligent quietly depends on…
Est. 65,000 EUR
Role Overview You’re a hands-on backend engineer who enjoys owning features end to end and working on real products that customers rely on every day. In this Software Engineer II role, you’ll help build and evolve a Thir…
Position Overview You are a highly operational, execution-focused project leader who is passionate about technology and innovation. In this role, you will lead customer adoption and implementation projects for Diligent’s…
You’ll shape the future of a business‑critical platform as the technical lead across both product engineering and cloud infrastructure. You’ll modernize a mature .NET application running on AWS today, while steering its…
Tired of just writing boilerplate? Ready to orchestrate, refine, and ship high-impact product features with modern agentic workflows? If you are a builder who pairs solid engineering fundamentals with cutting - edge AI d…
Est. 60,000 EUR
Position Overview: As a Senior Software Engineer at Diligent, you’ll be hands-on in shaping the future of our platform by designing and delivering secure, scalable, and high-performing microservices that power our SaaS s…
Position Overview Diligent is looking for an experienced GRC Advisor to join the team and work on Key accounts to drive adoption and retention and identify areas for expansion within our platform. This position will leve…
Role Overview As an Analyst II, Security Engineer, you’ll play a key role in keeping Diligent’s corporate systems, infrastructure, and cloud environments secure. You’ll work hands-on with modern security tools, partner w…
Here’s a summary of the role: You are a seasoned AI engineer ready to design, ship, and own production‑grade agentic systems that solve real enterprise problems. At Diligent, you’ll take technical ownership of Compliance…
Please note: This is a fully on-site position for the first six months, requiring attendance in the office five days per week.Overview Diligent's Commercial AI Transformation function builds AI agents that automate real…
Role Overview You’ll be the Principal Software Engineer driving the next generation of a large-scale enterprise SaaS platform. In this role, you combine deep hands-on engineering with high-impact technical leadership, sh…
Here’s a summary of the role: Diligent is seeking Advisory Specialists I (Risk & Audit) to join our growing Professional Services team. We're looking for individuals who are passionate about technology and consistent…
Est. 147,500 USD
Help shape the technology that enables a global organisation to do its best work. As Senior Manager, Platform Engineering, you’ll lead the team responsible for Diligent’s Atlassian and Microsoft platforms while setting t…
Est. 70,000 USD
Total Compensation: $60,000 base / $80,00 OTE Hiring Locations: Must be based in Washington DC/commutable distance Work Schedule: This is a hybrid position. 3 days in office in Washington DC (Tuesday, Wednesday and Thurs…
Est. 112,000 USD
Position Overview Diligent is looking for an experienced GRC Advisor to join the team and work on Key accounts to drive adoption and retention and identify areas for expansion within our platform. This position will leve…
Est. 84,000 EUR
Position Overview Spend your days making a difference, not just working for a living. At Diligent, we build Security, Risk Management, Compliance, and Audit software that helps uncover fraud, waste, environmental risks,…
Est. 80,000 GBP
Here’s a summary of the role: Diligent is seeking a Service Sales Manager (Risk & Audit) to join our Professional Services department. The Services Sales team works closely with Sales to ensure the appropriate profes…
Here’s a summary of the role: Diligent is seeking Advisory Specialists I (Risk & Audit) to join our growing Professional Services team. We're looking for individuals who are passionate about technology and consistent…
Here’s a summary of the role: If you enjoy solving customer problems, getting hands-on with web applications, and digging into issues rather than simply passing them on, this could be a great fit. As a Technical Support…
Est. 125,000 USD
Position Overview You are passionate about technology, creatively and commercially driven and are fully committed to a beautiful customer experience. Using your Project Management skills and experience, you will lead cus…
Est. 80,000 EUR
Position Overview: A Manager, Services allocates resources and ensures full team utilization while overseeing quality across the Professional Services customer journey. They coach and mentor the team, lead recruitment an…