Job Specifications
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
Position Overview
We are seeking a Director, Post-sales Strategy & Operations to partner with Professional Services and Support leadership in building a world-class, technology-enabled customer success organization.
You will define and execute the vision, strategy, and roadmap for post-sales excellence, leveraging AI and automation to scale operations and optimize customer experience.
Our products are used by over 23,000 organizations, including 62% of the Fortune 500, 90% of the FTSE 100, and 83% of the ASX 200. The ideal candidate will have a proven track record in building high-performing customer experience operations, with hands-on expertise in applying AI/ML to transform workflows and decision-making in SaaS environments.
In this role, you can expect the following responsibilities:
Recommend, lead, and execute the Professional Services and Support strategy, embedding AI and automation into processes to drive scale and drive incremental GDR lifts.
Partner with leadership teams to reimagine the post-sales customer journey through AI-powered insights and personalized experiences.
Identify and realize business opportunities and process improvements across PS and Support teams (e.g., automation for workflows such as case routing and onboarding sequences)
Establish automated dashboards to monitor business health and surface real-time recommendations for corrective action
Work with partners to drive the Professional Services and Support annual planning process, including bottom-up target setting
Introduce anomaly detection to proactively flag operational risks before they impact customer experience
Attract, grow, and retain top talent, cultivating strategic, operational, AI literacy and data fluency across the team
Champion a culture of innovation, experimentation, and continuous learning
To thrive in this role, you have:
10+ years of experience in a strategic, operations, and/or consulting role
5+ years managing high-performing teams
Experience with Salesforce and OpenAir (and other PS tools)
Strategic and Builder Mentality: Sharp analytical and problem-solving skills with a strong bias for action, thinking from first principles and delivering the best results
An AI Mindset: You are a strategic thinker with a bias for execution via AI. You naturally gravitate towards systems-thinking, automation, and applying design principles to solve operational challenges
Data-First and Analytically Rigorous: You have a proven ability to translate complex data into actionable business insights and strategic recommendations
Cross-Functional Leadership: Ability to lead cross-functional teams and collaborate across departments (Professional Services, Support, Customer Success, IT, Analytics) to ensure alignment and successful execution of Post-sales operations
Process Optimization: Strong understanding of business process optimization and automation, with experience redesigning and scaling processes to meet the needs of a growing organization
Leadership and Communication Skills: Strong leadership skills, with the ability to lead cross-functional teams, collaborate across departments, manage teams and engage with both technical and non-technical stakeholders. Ability to proactively communicate complex topics to diverse audiences
Adaptability & Execution: Ability to thrive in a fast-paced, ever-changing environment, managing multiple priorities and executing efficiently to achieve business goals
U.S pay range
$131,000—$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,
About the Company
Diligent created the modern governance movement. As the leading governance, risk and compliance (GRC) SaaS company, we serve 1 million users from over 25,000 customers around the globe. Our innovative platform gives leaders a connected view of governance, risk, compliance and ESG across their organization. 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 peo...
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