Senior Staff Software Engineer

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.

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Position Overview 

Diligent is transforming governance with intelligence. As a Senior Staff Software Engineer, Agentic AI, you will play a critical leadership role in shaping the next generation of Diligent's AI infrastructure and agentic solutions. Based in our Vancouver Center of Excellence, you'll drive architectural strategy and lead innovation across our AI Platform — the foundation that powers intelligent, secure, and scalable solutions across Diligent's product ecosystem. 

This is a senior-level technical role for a visionary engineer who thrives on solving complex problems, guiding architecture at scale, and applying AI to real-world enterprise challenges. You will partner closely with senior engineering, product, and research leaders to translate the latest advancements in AI — particularly large language models (LLMs) — into impactful, production-ready capabilities. 

Key Responsibilities 

• Architect and evolve Diligent's AI Platform to deliver scalable, reliable, and secure AI services that power data-driven decision-making for global organizations.
• Lead development of enterprise-grade AI applications leveraging LLMs, retrieval-augmented generation (RAG), and emerging multimodal AI technologies.
• Define and implement architectural best practices that ensure consistency, observability, and operational excellence across teams and services.
• Collaborate with applied science and product teams to accelerate innovation — turning cutting-edge models into differentiated product experiences.
• Champion the use of AI-assisted development tools to increase velocity, improve quality, and enhance the developer experience across the organization.
• Mentor and influence engineering leaders across multiple teams, fostering technical excellence and a culture of experimentation, learning, and impact.
• Stay ahead of industry trends in AI, cloud architecture, and software delivery — bringing fresh ideas and strategic insights to shape Diligent's technology roadmap.
• Represent Diligent's AI engineering vision in cross-functional initiatives and, when appropriate, in public forums, conferences, or technical communities. 

Required Experience/Skills 

• 10+ years of professional software engineering experience, with 5+ years in a senior or staff-level architecture or technical leadership role.
• Proven success designing and scaling cloud-native, event-driven architectures on AWS (or similar), including deep knowledge of serverless, microservices, and IaC (AWS CDK, Terraform, or similar).
• Strong experience developing AI applications using LLMs and related frameworks (e.g., LangChain, OpenAI SDK, AWS Bedrock, or Hugging Face).
• Ability to architect end-to-end AI systems — from data ingestion and model orchestration to API delivery, monitoring, and continuous improvement.
• Proficiency in Python and modern backend technologies; experience with TypeScript and React is a plus.
• Deep understanding of AI development lifecycle, including evaluation, prompt optimization, and observability for AI systems.
• Demonstrated ability to lead and mentor engineers, driving architectural alignment and improving development efficiency across multiple teams.
• Passion for continuous learning and staying at the forefront of emerging AI technologies and software architecture trends. 

Preferred Experience/Skills 

• Experience designing LLM applications and services at scale, including cost optimization and performance tuning.
• Familiarity with AI agent frameworks, and workflow orchestration (e.g., LangGraph, CrewAI, Semantic Kernel, or similar).
• Strong experience with DevOps and CI/CD in large-scale cloud environments. 

Pay Range

$130,000 - $180,000 CAD

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

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.

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