Director, AI Success Strategist, Customer Success

Job Description

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

How You’ll Make an Impact

Strategic 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 You’ll Need to Succeed

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.

Qualifications

• 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.

#LI-WO1

The US annualized OTE (On Target Earnings) range for this position is $227,000.00-$341,000.00 with a pay mix of 70/30 (base/commission). This position may also be eligible for bonus, benefits, or related incentives. While this range reflects the minimum and maximum value for new hire salaries for the position across all US locations, the offer for the successful candidate for this position will be based on job related capabilities, applicable experience, and other factors such as work location. Please note that the compensation details listed in US role postings reflect the base salary only (or OTE for commissions based roles), and do not include bonus, benefits, or related incentives.

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 [email protected] with your specific accommodation request.