Director, Customer Success - SMB​/MDO

Director, Customer Success - SMB/MDO

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The Director of Customer Success for SMB/MDO/Scaled CS is a senior leader responsible for driving customer outcomes, regional retention and growth, and the performance of a 30+ person Customer Success team. This role focuses on delivering world‑class customer experiences and exceeding metrics for gross and net revenue retention (GRR/NRR), renewals, product adoption, and customer satisfaction. You’ll provide strategic direction, develop operational processes, scale team capabilities, champion AI and automation use internally, and partner cross‑functionally to ensure the success of our clients across all segments and geographies within the region.

A primary focus is to ensure the team has the right skills and capabilities to effectively communicate and demonstrate Diligent’s value proposition, including partnering with the BUs and GTMR teams on enablement programs, and coaching team members to develop their direct reports as product advocates and experts. The role finds opportunities to continuously improve the way we target and engage clients, including renewal & expansion opportunities, leveraging AI and automation, and building scalable client engagement, retention, risk mitigation processes to proactively address client needs and improve retention.

Given the seniority of the role, this person will be a critical participant and leader for global Customer Success initiatives, requiring partnership with global CS and Post‑sales teams.

• Drive strategies to monitor customer health at scale, proactively mitigate risk, and optimize forecasting and expansion plans, leveraging data-driven insights and AI‑powered tools.
• Develop and manage high‑impact engagement strategies tailored for a high volume, low ACV customer base, partnering with Onboarding, Training, Professional Services, Customer Success Associates, and Support teams to help customers progress on their maturity curve.
• Create and iterate on digital‑first engagement and save plays to consistently deliver value and drive business outcomes for a large, diverse set of clients.

• Build, scale, and refine post‑sale operating models for high velocity, low ACV segments—including use of pooled resources and rapid‑response support alongside dedicated named account management.
• Drive the automation of key customer journeys through digital, tech touch, and AI‑enabled processes to deliver efficient, scalable support and engagement.
• Continuously enhance reporting capabilities to track team and customer outcomes, improve accountability, and refine retention forecasting. Ensure KPIs are set and achieved on a quarterly and monthly cadence.
• Manage the Customer Success budget with focus on high efficiency and optimized resource allocation for a hybrid team structure.
• Identify and execute on opportunities to further automate and streamline CS operations using technology and AI.

• Lead and mentor a hybrid Customer Success team—combining named account CSMs and a pooled CS account management model—to ensure rapid response to evolving customer needs.
• Foster a culture of performance, curiosity, learning, and collaboration. Champion product mastery across the team to drive stronger product advocacy and client adoption.
• Define clear role expectations, establish KPIs for each team member, and ensure ongoing accountability through structured performance management.
• Drive implementation of coaching, career development frameworks, and compensation strategies in alignment with HR, Finance, and global CS leadership.
• Communicate transparently and frequently to keep teams motivated, informed, and aligned—celebrating successes and learning from challenges.

• Partner with Sales, Account Management, and other Post‑Sales teams (Onboarding, Training, Professional Services, Support) to shape expansion and renewal strategies and maximize the customer lifecycle value for high volume, low ACV accounts.
• Collaborate horizontally with product, engineering,…