The Team

Our Business Applications and Analytics team plays a pivotal role in driving business success through data-driven decision-making and operational excellence. This dynamic team manages enterprise-wide applications, including ERP, CRM, and BI systems. By harnessing the power of data and advanced analytical tools, we provide valuable insights that inform strategic initiatives, optimize processes, and enhance overall performance. Within this team sits our AI Solutions group, a small, high-impact squad of AI Solutions Architects partnering with AI Solutions Engineers building and scaling internal AI/GenAI capabilities across the company. This is the team you will lead.

Position Overview

Diligent is ‘All-In’ on AI and is seeking an experienced, hands-on leader to head our AI Solutions Architecture function as a Senior Manager / Director. You will lead a team of six, a mix of AI Solutions Architects and AI Solutions Engineers, responsible for identifying, designing, building, and scaling AI/GenAI solutions that accelerate our internal AI capabilities across Marketing, GTM/Sales, Customer Success & Support, Finance, HR, Legal, and Product & Engineering. This is both a people-leadership and a technically heavy role with expectation to get your hands dirty. You will own the strategy, roadmap, and delivery of the internal AI portfolio: setting technical direction and architectural standards, coaching and growing the team, partnering with senior business stakeholders to prioritize the highest-value opportunities, support execution, and ensuring every solution is delivered securely, responsibly, and with measurable ROI. The ideal candidate pairs strong AI/GenAI and enterprise-systems fluency with a track record of building and leading high-performing engineering or solutions teams, and can move comfortably between executive conversations and technical delivery.

Alongside the internal AI portfolio, this role required to partner with platform engineering for a number of Diligent’s core IT platforms including Salesforce, Gainsight, Atlassian, Snowflake, Workday, Netsuite and the Microsoft ecosystems taking accountability for their continued modernization and for embedding AI capability into them where it drives value. The ideal candidate pairs strong AI/GenAI and enterprise-systems fluency with a genuine builder’s track record and experience leading high-performing engineering or solutions teams, and can move comfortably between executive conversations, deep technical review, and hands-on delivery.

Key Responsibilities

Leadership & Team Development Lead, coach, and grow a team of five AI Solutions Architects and Engineers — setting clear goals, providing regular feedback, and supporting career development and technical growth. Own hiring and capability planning for the function: attract, retain, and develop top AI/engineering talent, and shape the team structure as the portfolio scales. Foster a culture of experimentation, rapid iteration, engineering excellence, and responsible AI, where the team learns fast and shares findings openly. Balance leadership with hands-on depth stay technically credible enough to review designs, unblock the team, and make sound architectural trade-off decisions.

Strategy & Roadmap

Define and communicate the strategy, vision, and roadmap for internal AI solutions, aligned to Diligent’s business goals and operating priorities. Partner with senior business leaders across Marketing, GTM/Sales, Customer Success & Support, Finance, HR, Legal, and Product & Engineering to identify, prioritize, and act on the highest-value AI opportunities. Develop and steward architectural standards, reusable patterns, and reference implementations that the Architects design and the Engineers build against, ensuring consistency and reuse across the portfolio. Manage the portfolio and its trade-offs — sequencing initiatives, allocating team capacity, and balancing quick wins against durable, scalable platform investments.

Delivery & Technical

Operate as a player-coach actively contribute to hands-on build work (prototypes, reference implementations, integrations, and unblocking complex problems), adding real delivery capacity to the team rather than managing from a distance. Oversee the end-to-end lifecycle of AI solutions from ideation and prototyping through production deployment, monitoring, tuning, and operational handover. Ensure solutions embed AI/GenAI capabilities (RAG, copilots, agents, summarization, classification) into core business applications such as ERP, CRM, and BI in a robust, maintainable, and user-friendly way. Champion quality and reliability driving standards for architecture reviews, testing, observability, cost management, and incident response across the team’s work. Establish and track KPIs and ROI for AI initiatives, monitoring the performance and effectiveness of deployed solutions and continually refining them.

Governance, Responsible AI & Stakeholder Management

Champion responsible AI privacy, security, fairness, and ethical guidelines — and ensure compliance with data protection and regulatory requirements across all implementations. Act as the primary point of contact and trusted advisor to business and executive stakeholders on internal AI capability, translating technical possibilities into clear business value. Drive AI and data literacy across the organization through enablement, workshops, and reusable documentation, runbooks, and playbooks. Stay abreast of AI advances — tools, patterns, and methodologies — and introduce the right ones to the organization at the right time.

Required Qualifications

Bachelor’s degree in Computer Science, Engineering, AI/ML, Data Science, or a related field (or equivalent experience); an advanced degree is a plus. 8+ years in software, data, or solutions engineering, including experience building and operating production AI/GenAI or enterprise systems. 3+ years of people leadership managing and developing engineers, architects, or technical solutions professionals, ideally including hiring and performance management. Proven track record of setting technical direction and delivering enterprise-scale AI/GenAI or software solutions with measurable business impact. Strong, current understanding of AI/GenAI patterns LLMs, prompt engineering, RAG, agents/workflows, and output evaluation and the judgment to apply them appropriately. A genuine builder who leads from the front (player-coach): still writes code and delivers hands-on, with proficiency in at least one modern language (e.g., Python, TypeScript/Node.js, Java, or C#), APIs and integrations, and cloud platforms (AWS preferred; Azure/GCP welcome). Experience owning or engineering enterprise IT platforms the Atlassian suite, the Microsoft ecosystem (M365 / Azure), or comparable including configuration, integration, automation, and lifecycle management. Experience integrating AI/GenAI into enterprise systems such as Salesforce/CRM, ERP, or BI/analytics platforms. Strong grasp of responsible AI, privacy, security, and compliance in a regulated or enterprise SaaS context. Excellent communication and stakeholder-management skills able to influence senior business leaders and explain technical trade-offs to non-technical audiences. Experience leading cross-functional, globally distributed teams across business, data, security, and operations.

Preferred Qualifications

Experience standing up or scaling an internal AI / AI enablement function within a global SaaS or enterprise organization. Familiarity with MLOps/LLMOps concepts, model lifecycle, experiment tracking, evaluation, and drift monitoring, and with containerization and CI/CD. Exposure to classical ML/analytics (e.g., Scikit-learn, dashboards) sufficient to guide and collaborate with data and ML teams. Prior experience in a global SaaS company operating across India, North America, and EMEA time zones. Strategic thinker with strong analytical and problem-solving skills and a demonstrated ability to drive measurable outcomes through AI/GenAI.

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. 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 recruitment@diligent.com. 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: https://www.diligent.com/legal/candidate-privacy 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.