Principal AI Success Strategist, Customer Success

Job Description Why This Role? Why Now? Customer experience is transforming through AI-driven innovation. At Zendesk, we don’t just embrace this change — we lead it. As visionary architects of our AI-powered Resolution Platform, AI Success Strategists shape and deliver long-term AI success for our customers. This role transcends technical deployment; it is about owning the strategic AI roadmap, maximizing business impact, and builds executive partnerships from day one so AI initiatives start strong and scale predictably. Mission You will own end-to-end delivery of customers’ AI roadmaps: translating product capabilities into clear business strategies, defining a long-term AI vision, aligning internal and external teams, and driving execution from initial adoption through sustained expansion. Your success is measured by high customer satisfaction, increased automated resolution usage, and improved retention—while orchestrating the right mix of product, services, and partner resources. You will lead structured discovery and success-planning engagements that create measurable playbooks and milestones early in the lifecycle. Overarching Objective For The Role: Accelerate customers’ time‑to‑value by driving adoption and operational excellence for Zendesk AI solutions, ensuring customers realize measurable business impact from initial deployment through scale Own customers’ multi‑year AI roadmap and execute cross‑functional delivery—aligning Product, Services, Sales, and Partners to scale safe, sustainable AI programs Deliver quantifiable commercial outcomes —protect renewals, grow account expansion, and translate AI adoption into predictable revenue and retention improvements How You’ll Make an Impact Strategic Responsibilities Full Ownership of AI Roadmap Delivery: Lead the design, planning, and execution of comprehensive AI adoption and expansion roadmaps for key customers, ensuring alignment to their broader business goals and customer success vision. Design Authority: Serve as the design authority for customers’ AI deployments — lead solution design reviews, ensure deployments align with the latest best practices and collaborate with Professional Services on integration and configuration guidance. For complex agent implementations, coordinate troubleshooting and technical escalations with Professional Services, Product and Engineering to resolve blockers quickly. Long-term AI Vision & Business Strategy: Partner with executive stakeholders to co-create and refine a forward-looking AI strategy that anticipates market trends and customer needs. Serve as the primary AI thought leader and trusted advisor throughout the engagement lifecycle. Internal and External Stakeholder Alignment: Dedicate effort to internal cross-functional collaboration, aligning Product, Professional Services, Sales, Success, and other teams to deliver on the AI roadmap. Serve as the Engagement Lead: Coordinate and sequence activities, identify and escalate risks early, and ensure the right technical, product, and services resources are engaged at the appropriate times. Sustain Engagement & Mutual AI Roadmap: Maintain recurring outcome-driven cadences and mutual AI Roadmap that define strategic goals, shared initiatives, measurable success, and a roadmap to maximize value and secure renewal. Channel & Adoption Strategy: Own the channel strategy for AI solution dissemination and adoption, balancing direct customer delivery with channel enablement and partner engagement. Measure and Drive Impact: Utilize data-driven insights to track AI adoption, resolution metrics, and gross revenue retention improvements. Continuously refine strategies to optimize outcomes and customer satisfaction. Responsible AI & Compliance: Confidently advise customers on ethical AI practices, data governance, and compliance considerations — framing use cases within safe, explainable, and policy‑aligned guardrails. What You’ll Need to Succeed Strategic Skills & Expertise Project & Program Management: Proven ability to orchestrate multi-phase technology adoption projects, managing diverse teams and timelines with clarity and agility. Product and Technical Knowledge: Product expert who assesses customers' use case automation potential and technical readiness (generative AI, integrations, authentication), helps craft user journeys and translates features into value. Liaise with ProdDev teams to remove blockers for adoption, implement fixes and provide feedback on (beta) features. Business & Strategic Acumen: Demonstrated skill in aligning AI solutions to customer business challenges, driving revenue growth, and influencing executive decision-making. Consultation & Communication: Strong stakeholder engagement skills—whether customer executives or internal teams—to advance AI adoption and sustain strategic partnerships. Analytical & Outcome-Focused: Strong analytical capacity to interpret adoption data, develop predictive health scores, forecast retention/expansion, and translate metrics into prioritized action plans. Forward-Thinking & Pragmatic: Visionary in embracing AI’s potential with a grounded, realistic approach to execution—balancing innovation with practical delivery feasibility. Qualifications Must have a minimum of 10+ years of related experience in Customer Success / Experience, 2+ years of AI related experience Previous experience in go-to-customer/GTM roles in enterprise technology / SaaS — either customer success management, professional services/consulting, technical account management, or solutions engineering/pre-sales consulting Demonstrated experience in using adoption and health analytics to forecast churn and expansion; surface early risk signals and recommended mitigations to secure retention and growth. Bachelor’s degree in Business, Computer Science, Engineering, or related field; advanced degrees; certifications in AI strategy or project management preferred. Experience managing AI or software adoption programs with demonstrated impact on business metrics such as retention or satisfaction. Demonstrated experience designing and executing success plans or roadmaps that drive measurable customer outcomes Excellent program management and cross-functional influence skills. Familiarity with emerging AI trends is a plus Ability to distill complex AI concepts for diverse audiences, especially executive stakeholders. Great to have AI Domain Expertise: Deep understanding of AI capabilities within Zendesk’s platform, not necessarily hands-on technical, but sufficient to translate product features into business value and strategic initiatives. The intelligent heart of customer experience Zendesk software was built to bring a sense of calm to the chaotic world of customer service. Today we power billions of conversations with brands you know and love. Zendesk believes in offering our people a fulfilling and inclusive experience. Our hybrid way of working, enables us to purposefully come together in person, at one of our many Zendesk offices around the world, to connect, collaborate and learn whilst also giving our people the flexibility to work remotely for part of the week. As part of our commitment to fairness and transparency, we inform all applicants that artificial intelligence (AI) or automated decision systems may be used to screen or evaluate applications for this position, in accordance with Company guidelines and applicable law. Zendesk is an equal opportunity employer, and we’re proud of our ongoing efforts to foster global diversity, equity, & inclusion in the workplace. Individuals seeking employment and employees at Zendesk are considered without regard to race, color, religion, national origin, age, sex, gender, gender identity, gender expression, sexual orientation, marital status, medical condition, ancestry, disability, military or veteran status, or any other characteristic protected by applicable law. We are an AA/EEO/Veterans/Disabled employer. If you are based in the United States and would like more information about your EEO rights under the law, please click here . Zendesk endeavors to make reasonable accommodations for applicants with disabilities and disabled veterans pursuant to applicable federal and state law. If you are an individual with a disability and require a reasonable accommodation to submit this application, complete any pre-employment testing, or otherwise participate in the employee selection process, please send an e-mail to with your specific accommodation request.