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:
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.
Key Responsibilities
Customer Outcomes & Strategy
- 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.
Operational Leadership
- 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.
Team Leadership & Development
- 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.
Strategic Collaboration
- 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.
Customer Voice & Advocacy
- 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.
Required Experience/Skills
Experience:
- 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
- Preferred experience within the not-for-profit and public sector including school board administration and local community government
- Proven track record of meeting or exceeding retention, expansion and client satisfaction targets
- Location in New York, Washington D.C. or Vancouver is desirable
Skills:
- 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.
Leadership:
- 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.
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 [email protected].
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.
