Director, AI Success Strategist, Customer Success

Zendesk • New York, NY

19d • $227,000 - $341,000 • Hybrid

About The Position

Why This Role? Why Now? As Zendesk scales AI across the market, we need leaders who can convert product innovation into predictable, company-level outcomes. The Director will lead multiple teams of AI Success Strategists, setting strategy and operational rigor for AI adoption across a large portfolio. This is a strategic, high-impact role: you’ll partner with senior Product and GTM leaders and own org-level outcomes that directly affect revenue, retention, and product roadmaps. Mission You will own strategy, operations, and outcomes across a broader AI Success organization (~15–30 people; managers reporting in). You’ll ensure the organization scales repeatable, measurable AI programs, drives product adoption at scale, and provides executive-level forecasting and risk management that informs company strategy. Overarching Objective For The Role: Define and deliver org‑level strategy for ~15–30 people that translates product innovation into market outcomes — accelerate product adoption at scale, drive measurable improvements in retention and expansion (GRR/NRR), and increase portfolio ROI on AI investments Build forecasting, predictive health models and executive reporting that materially improve forecast accuracy, lower portfolio churn, and enable data‑driven product and GTM prioritization — so leadership can make investment decisions with confidence Architect the people, governance and cross‑functional playbooks (including responsible‑AI guardrails) that let managers scale repeatable, measurable AI programs — reducing deployment risk, standardizing executive engagements, and creating scalable motion for revenue and product roadmap influence

Requirements

• Strategic Skills & Expertise Product partnership track record: Demonstrable experience turning portfolio adoption signals into prioritized roadmap investments, pilots, or betas with Product/ProdDev.
• Forecasting & risk management outcomes: Implemented forecasting/predictive health models and executive reporting that improved forecast accuracy or materially reduced churn.
• Operational scale experience: Defined/playbooked KPIs, SLAs and tooling for cross‑functional delivery across Sales/Services/Product/Partners.
• Executive presence: Regularly advised C‑suite customers and presented board‑quality trend/forecast analysis to senior leadership.
• Commercial impact: Proven ownership for team targets (GRR/NRR, adoption, expansion) with measurable ROI or revenue outcomes.
• Change & strategic judgment: Evidence of converting insights into prioritized product asks, GTM pivots, or investment decisions that moved company metrics.
• Mindset: Entrepreneurial/ownership mentality; comfortable operating in ambiguity while enforcing disciplined accountability and measurement.
• 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.

Responsibilities

• Org leadership & people strategy: 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.
• Strategic product partnership & roadmap influence: Be the voice of the customer by turning portfolio signals into prioritized product and GTM investments. Partner with Product to accelerate measurable adoption.
• Operational ownership & cross‑functional coordination: 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.
• Executive engagement & external relationships: 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.
• Portfolio‑level risk forecasting & business insight: 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.
• Commercial outcomes & growth: 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.
• Responsible AI governance & policy guidance: 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.

What This Job Offers

• Job Type: Full-time
• Career Level: Director