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Diligent · 1 day ago

Director, Customer Success - SMB/MDO

Washington, DC

Full-time

Hybrid

Lead/Staff, Director/Executive

$151K/yr - $189K/yr

5+ years exp

Diligent is an AI leader in governance, risk and compliance SaaS solutions. The Director of Customer Success for SMB/MDO/Scaled CS is responsible for driving customer outcomes, retention, and the performance of a large Customer Success team, focusing on delivering exceptional customer experiences and strategic direction.

Business IntelligenceCollaborationComplianceData CenterInformation TechnologyMeeting SoftwareMessagingRisk ManagementSaaSSoftware

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 - 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

Qualification

Customer Success strategyCS metrics expertiseExperience in B2B SaaSLeadership of large teamsAIAutomation proficiencyChange management expertiseCross-functional collaborationExecutive-level communicationCommercial acumenTeam development

Required

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 strategy and able to identify and build a team structure that provides optimal support ecosystem across the region

Ability to manage and navigate executive level conversations to drive departmental behaviors across all lines of the business