Transformation Lead

Position: Sr. Director, Customer Success Transformation Location: Remote Duration: 6+ months

Job Description: Our Client help organizations create better customer experiences through AI-powered experience orchestration. Our platform connects people, systems, data and AI to help organizations deliver more personalized service, improve operational efficiency and build stronger customer relationships. Help build, support and operate technology used by more than 8,000 organizations in over 100 countries moving AI from possibility to production in real-world enterprise environments every day.

About the Role: The Client is seeking a strategic and execution-focused Senior Director, Customer Success Transformation to help define and drive the future of our global Customer Success organization, with an initial focus on Professional Services and the broader Customer Success operating model. In this role, you will serve as a strategic partner to the Head of CS Transformation and a key architect of the future Customer Success operating model. You will define what that future model looks like and how the pieces fit together - connecting customer engagement, Professional Services, scaled and digital motions, talent, commercial models, technology, and AI into a coherent system for creating customer value at scale. You will translate that architecture into a transformation portfolio and lead the most strategic initiatives required to make it real.

The ideal candidate combines enterprise transformation leadership with strong operating-model architecture skills: someone who sees the organization as an interconnected system, challenges existing assumptions, defines future-state choices, and translates complex ideas into practical models leaders and teams can execute.

You will bring strong understanding of Customer Success, Professional Services, and customer-facing SaaS operating models, with the executive presence to influence senior leaders across a global matrixed organization.

• Architect the future-state Customer Success operating model, defining how customer engagement, Professional Services, scaled and digital motions, talent, technology, AI, and commercial models work together to create scalable customer value.
• Partner with executive leadership to define strategic choices, transformation priorities, and multi-year roadmaps that align Customer Success with company strategy, customer needs, and growth objectives.
• Connect transformation initiatives into a coherent portfolio, sequencing priorities such as Professional Services transformation, AI acceleration, A2O, talent evolution, new offers, and scaled Customer Success around a common future-state model.
• Lead the most strategic and ambiguous transformation initiatives from problem definition and future-state design through incubation, proof, scale, and transition into the business, driving measurable outcomes and sustained adoption.
• Design new operating and commercial models that enable standardization, productization, continuous value realization, and scalable growth, working across Sales, Product, Finance, Operations, HR, Enablement, and Innovation.
• Translate AI and emerging technologies into business transformation opportunities, identifying where AI can change roles, workflows, delivery models, and customer engagement in partnership with AI and Innovation leaders.
• Build compelling executive narratives, decision frameworks, and governance mechanisms that clarify choices, trade-offs, risks, and business impact and enable senior leaders to act.
• Build trusted relationships with senior leaders and influence decisions without direct authority, creating alignment and momentum while challenging conventional thinking and existing ways of working.

• 10+ years of experience in strategic transformation, operating model design, strategy, business operations, or related leadership roles within enterprise SaaS or technology organizations.
• Demonstrated experience designing and implementing new operating models, business models, customer-facing capabilities, or transformation strategies, not simply managing projects or programs.
• Deep understanding of Customer Success, Professional Services, and/or customer-facing SaaS operating models, with the ability to connect customer lifecycle, services, commercial, and operational perspectives.
• Strong understanding of recurring-revenue SaaS economics and the ability to connect customer outcomes to growth, retention, expansion, services performance, and scalable delivery.
• Experience translating AI and emerging technology capabilities into business and organizational transformation opportunities, and leading complex global change in highly matrixed organizations.
• Exceptional strategic problem-solving and executive influence, with the ability to move between strategy and operational detail, create structure in ambiguity, and influence senior stakeholders without formal authority.
• Strong commercial, analytical, and financial acumen, with a data-driven approach to identifying opportunities, building business cases, prioritizing investments, and measuring impact.
• Experience driving organizational change and adoption across geographically dispersed teams, with a strong builder mindset and bias toward creating capabilities that scale into the broader organization.
• Bachelor's degree or equivalent experience; advanced degree preferred.

For applications and inquiries, contact:View email address on us.fitly.work