[Remote] Director, AI Success Strategist, Customer Success

Note: The job is a remote job and is open to candidates in USA. Zendesk is a company focused on enhancing customer service experiences, and they are seeking a Director, AI Success Strategist to lead teams in driving AI adoption. This role involves setting strategy and operational rigor for AI initiatives, partnering with senior leaders to influence product roadmaps and improve company outcomes.

Responsibilities

• Own hiring, org design, and talent development for the AI Success org (~15–30). Scale managers, build clear career frameworks and learning programs, and track employee satisfaction, promotion velocity, and retention
• Be the voice of the customer by turning portfolio signals into prioritized product and GTM investments. Partner with Product to accelerate measurable adoption
• Define playbooks and KPIs to ensure consistent delivery at scale. Own handoffs and tooling across Sales, Services, Product, Partners, Legal, and Finance so teams can context‑switch quickly and execute reliably
• Own C‑level relationships for strategic customers and represent Zendesk in various events. Standardize executive briefings and coach managers to run scalable, outcome‑focused C‑suite interactions
• Build top‑down forecasting and predictive health signals that aggregate trends across portfolios and regions. Surface prescriptive mitigations to senior leadership and own improvements in forecast accuracy and churn reduction
• Set and own team‑level targets for adoption, GRR/NRR, and expansion velocity. Partner with Sales, Finance, and RevOps on quota targets, renewal plays, and ROI-driven scaling or pivot decisions
• Define practical guardrails for safe, explainable, and compliant AI deployments. Operationalize requirements with Product, Legal, and Security, and ensure ongoing training/certification across the org

Skills

• 12+ years of experience in Customer Success, Professional Services, Technical Account Management, Solutions Consulting, or similar enterprise SaaS roles; 3+ years in roles focused on AI adoption or AI products go‑to‑market
• 5+ years of people leadership with experience managing managers and scaling teams (responsible for ~15–30 people, including manager layers)
• 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
• Proven experience partnering with senior Product leadership and influencing product roadmaps based on customer outcomes and usage data
• Strong record of working with executive stakeholders (customer C‑suite and internal executive leadership) and presenting business-critical forecasts and trend analyses
• Strategic mindset with deep business acumen — comfortable owning outcomes that intersect with revenue, product, and GTM strategy
• Exceptional communication skills and a proven track record of developing leaders and high-performing teams
• Advanced degrees; certifications in AI strategy or project management preferred

Benefits

• Bonus
• Benefits
• Related incentives

Company Overview

• Zendesk develops a customizable customer service platform for organizations. It was founded in 2007, and is headquartered in San Francisco, California, USA, with a workforce of 5001-10000 employees. Its website is http://zendesk.com.

Company H1B Sponsorship

• Zendesk has a track record of offering H1B sponsorships, with 50 in 2025, 69 in 2024, 37 in 2023, 92 in 2022, 93 in 2021, 44 in 2020. Please note that this does not guarantee sponsorship for this specific role.

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