Director, Customer Success - SMB/MDO

Diligent•New York, NY

40d•Hybrid

About The Position

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 of this role is to ensure the team have the right skills and capabilities to effectively communicate and demonstrate Diligent's value proposition. This also includes partnering with the BUs and GTMR teams on enablement programs, and coaching team members to develop their direct reports as product advocates and experts. This role finds opportunities to continuously improve the way we target and engage clients, including renewal & expansion opportunities, and including leveraging AI and automation. A key focus is 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.

Requirements

5+ years in customer-facing roles within B2B SaaS, 5+ years in a senior CS leadership role (team lead, manager of a CS discipline.
Demonstrated success leading post-sales functions (CS, Onboarding, Renewals, Support - or if only one, then CS) in smaller ACV accounts
Developed team-level KPIs to drive towards a high-performing team of CS professionals
Deep understanding enterprise software/SaaS market
Proven track record of meeting or exceeding retention, expansion and client satisfaction targets
Develop and execute on CS strategy to drive client retention, satisfaction and product engagement
Strong command of CS metrics: NRR, GRR, CSAT, time-to-value, health scores.
Strategic thinker with hands-on experience building segmentation and engagement models.
Proficient in CS tech and analytics tools (e.g., Gainsight, Salesforce). Has already leveraged AI and automation to build efficiency, scale and drive better client experiences.
Able to operate at both strategic and tactical levels; comfortable with ambiguity.
Skilled in executive-level communication, customer engagement, and cross-functional influence.
Strong commercial acumen, with fluency in sales and expansion methodologies.
Experience leading geographically distributed, multi-layered, high performing teams.
Experience leading a team of 20+ and managing at least 4 people leaders
Track record of hiring A players in all levels of former organizations
Expertise in change management, team design, and organizational scaling.
Ability to influence internal stakeholders and align teams around customer outcomes.
Passionate about developing leaders and reinforcing a high-trust, high-performance culture.
Strong understanding of Diligent solution strategyâ¯andâ¯able to identify and build a team structure that provides optimal support ecosystem across the region
Ability to manage and navigate executiveâ¯levelâ¯conversations to drive departmental behaviorsâ¯acrossâ¯all lines of the business.

Nice To Haves

Preferred experience within the not-for-profit and public sector including school board administration and local community government
Location in New York, Washington D.C. or Vancouver is desirable

Responsibilities

Take ownership of all core Customer Success metrics, including Gross Revenue Retention (GRR), Net Revenue Retention (NRR), Client retention, renewals, adoption, usage, and satisfaction across Diligent's Mission Driven Organization brands (average ACV <$8K).
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, enablement, marketing, community, and training teams to influence product roadmaps, scale customer education, and elevate engagement programs.
Analyze geographic and market data to identify growth opportunities and optimize go-to-market strategies specifically for Mission Driven Organization brands.
Lead strategic visioning and planning as part of annual business cycles, ensuring CS operations are aligned to company priorities.
Serve as the regional advocate for the voice of the customer, representing Mission Driven Organization brands in internal forums and strategy sessions.
Facilitate and scale customer advocacy programs, including digital reference and peer communities, to strengthen engagement and loyalty.
Embed a unified, customer-first mindset and drive alignment on shared KPIs across CS and cross-functional teams.
Capture and synthesize ongoing customer feedback using digital and tech touch methods to inform product development and complementary service enhancements.

Benefits

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

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