Director, Post-sales Strategy & Operations

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—$164,000 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 View email address on swooped.co .

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.