You love turning real business problems into working AI solutions — and you’re not afraid to roll up your sleeves to ship them. In this role, you’ll lead Diligent’s internal AI Solutions function, a small, high-impact team that is embedding AI and GenAI into the systems thousands of colleagues use every day across Marketing, Sales, Customer Success, Finance, HR, Legal, and Product & Engineering.
You’ll set the AI vision and roadmap for internal tools, architect solutions, and still build hands-on — from prototypes and reference implementations through to production-grade integrations. You’ll own how AI shows up inside ERP, CRM, BI and core IT platforms, and you’ll be accountable for making those solutions reliable, secure, compliant, and measurably valuable for the business.
If you enjoy being a “player-coach” who can move seamlessly between executive conversations and deep technical reviews, this role gives you the scope, visibility, and impact to shape how a global SaaS leader uses AI to run smarter and faster.
Here’s a breakdown of what you’ll do (not all of it, just the important stuff)
- Lead, coach, and grow a high-performing team of AI Solutions Architects and Engineers, setting clear goals and building the capabilities the business needs as AI demand scales.
- Define and own the strategy, vision, and roadmap for internal AI solutions, translating business priorities into a focused portfolio of AI and platform initiatives.
- Design and deliver end-to-end AI/GenAI solutions — from ideation and prototyping through production deployment, monitoring, and continuous improvement.
- Embed AI capabilities (such as RAG, copilots, agents, summarization, and classification) into core business applications including ERP, CRM, BI, and other enterprise systems in a robust, maintainable way.
- Act as a trusted advisor to senior and executive stakeholders, turning technical possibilities into clear business value and measurable KPIs and ROI for AI initiatives.
- Champion responsible AI, governance, and security — ensuring privacy, fairness, and regulatory compliance, and driving AI and data literacy through enablement, documentation, and workshops.
These are the essentials you’ll need to get an interview
- Proven “player-coach” experience: you still build hands-on (coding, standing up prototypes/reference implementations, unblocking hard problems) rather than managing AI delivery from a distance.
- Track record of building, leading, and developing technical teams, including hiring, performance management, capability planning, and career development.
- Deep, current AI/GenAI expertise with LLMs, RAG, agents/workflows, prompt engineering, and evaluation, with enough technical depth to review designs and make sound architecture trade-offs.
- Strong background in IT platform engineering for enterprise tools such as the Atlassian suite and Microsoft 365/Azure (or comparable), including configuration, integration, automation, lifecycle management, and ownership of reliability and security.
- Hands-on experience integrating AI into core business platforms (for example Salesforce/CRM, ERP, BI) via APIs and cloud infrastructure (AWS preferred), with solutions running successfully in production.
- Proven ability to own strategy, roadmap, and portfolio for AI and platforms — sequencing initiatives and allocating team capacity across competing demands.
- Confidence working with senior business and IT leaders, including accountability for KPIs/ROI and for responsible AI, security, and compliance across everything shipped.
It would be great if you had these too, but we’ll support you if you don’t
- Experience building or scaling an internal AI or AI enablement function in a global SaaS or large enterprise environment, ideally operating across multiple regions and time zones.
- Familiarity with MLOps/LLMOps practices (model lifecycle, experiment tracking, evaluation, drift monitoring) and modern engineering practices such as containerization and CI/CD.
- Exposure to classical machine learning and analytics (for example Scikit-learn, dashboards) and the ability to collaborate effectively with data and ML teams.
Diligent is an equal opportunity employer. We celebrate diversity and are committed to creating an inclusive environment for all employees.
Pay Range
$131,000—$164,000 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 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.
To support a fair and consistent hiring process, we use AI and digital automated tools to assist our recruitment team in organizing candidate data, surfacing relevant applications, coordinating interview scheduling and summarizing interview notes. All final screening, evaluation, and hiring decisions are made by humans on our team. To learn more about how we collect, protect, and process your information, please review our
Candidate Privacy Policy.
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.
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