Principal AI Success Strategist, Customer Success

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 building 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.
• 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.
• 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.
• Responsible AI & Compliance: Confidently advise customers on ethical AI practices, data governance, and compliance considerations.

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.
• 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 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.

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.
• Demonstrated experience in using adoption and health analytics to forecast churn and expansion.
• 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.
• 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.