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Director of Enterprise AI Success.

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Remote from
USA
Salary
USD 180k–245k / yr
Employment
Full Time
Experience
Director
Published
Apply before
26 Nov 2026
Listing views
32
Application actions
3
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AI Summary

The role, at a glance.

Cresta is seeking a senior customer-success leader to manage and develop Enterprise AI Success Managers serving complex enterprise accounts. The role is accountable for customer adoption, measurable value realization, renewals, risk management, and expansion across an AI SaaS portfolio. It requires close collaboration with Sales, Product, Engineering, Marketing, and Professional Services while building scalable operating practices and coaching systems. The successful candidate combines executive customer leadership, data-driven portfolio management, and practical fluency with AI-enabled SaaS products. Approximately 25% travel and cross-time-zone work are expected.

Role DNA

A quick view of the complexity, pace, ownership and collaboration implied by the job description.

Job Complexity

5/5
EasyHard

Pace & Pressure

5/5
RelaxedFast-paced

Autonomy Level

5/5
GuidedFull ownership

Communication Load

5/5
IndependentCollaborative
AI insightThis is a high-stakes leadership role responsible for enterprise retention and expansion while scaling a team in a rapidly changing AI product environment. Success requires balancing strategic customer outcomes, technical product fluency, people leadership, and cross-functional influence.

Salary analysis

Estimated compensation compared with the broader US market for similar roles.

Estimated job median (per year)Market rate
$212,500
US market range (per year)$180k–$260k
AI insightThe yearly pay period is inferred from the job context; it was not explicitly stated by the employer. The employer discloses a base salary range of $180,000–$245,000 USD. The annual cadence is inferred from the professional US base-salary range and full-time director-level role, as the posting does not explicitly state a pay period. Estimated US market base pay for comparable enterprise customer-success director roles is approximately $180,000–$260,000 USD per year, excluding bonus and equity.

Core skills

Skills and capabilities most closely associated with this opportunity.

Sample interview questions
How would you create a consistent operating rhythm for a team managing a large portfolio of complex enterprise AI customers?

I would establish a tiered account framework, standardized success plans, health-score reviews, and regular portfolio inspections. I would use adoption, business-value, risk, renewal, and expansion indicators to focus coaching and executive intervention on the accounts with the greatest impact.

Describe how you would help an enterprise customer move from AI experimentation to measurable business value.

I would begin by aligning leaders on priority business outcomes and baseline metrics, then define a phased adoption plan with accountable owners. The team would measure usage, workflow changes, and performance improvements, review results regularly, and use those findings to expand successful use cases.

How do you coach Success Managers to have credible technical conversations without turning them into implementation specialists?

I set clear expectations for product fluency around core configuration, workflows, prompts, rules, and data-driven troubleshooting. Coaching focuses on connecting those capabilities to the customer's operating goals while engaging technical specialists early when deeper implementation expertise is required.

What actions would you take when an important enterprise account shows declining adoption before renewal?

I would quickly validate the root cause through usage data, stakeholder interviews, and a review of the original success criteria. I would then coordinate a recovery plan with executive sponsorship, concrete adoption milestones, owner accountability, and a frequent review cadence shared with the customer.

How would you partner with Sales while maintaining a customer-first success organization?

I would create shared account plans, transparent health signals, and agreed rules for identifying expansion opportunities. Sales and Customer Success should jointly pursue growth only where measurable customer value and adoption readiness are established, protecting long-term trust and retention.

This analysis is generated from the job description. Salary estimates, role characteristics and sample answers are guidance, not employer-provided facts.
Opportunity details

About this role.

Cresta unlocks the true potential of the customer experience, turning every conversation into a competitive advantage. Cresta’s unified AI platform combines conversational AI agents, real-time human agent augmentation, and comprehensive conversation intelligence to drive revenue and efficiency gains across every channel. The world’s leading companies, including United Airlines, Cox Communications, and Marriott, use Cresta to power world-class customer experiences every day.

Born from the Stanford AI Lab, Cresta has raised more than $270 million from the world’s leading investors, including a16z, Greylock, and Sequoia. Cresta’s leadership includes some of the leading minds in AI today. Our CEO, Ping Wu, founded and led Google’s Contact Center AI and Vertex AI platforms before joining Cresta to build the future of AI-driven customer experiences.

Over the next few years, AI is going to redefine how people all over the world interact with businesses every day. Come build that future at Cresta.

About the Role:

As the Director of Enterprise Customer Success at Cresta, you will lead and develop a high-performing team of AI Success Managers supporting our enterprise customers.

Customer Success at Cresta has evolved beyond a traditional relationship-management model. Our AI Success Managers operate as a hybrid of strategy consultant, AI product expert, and account owner—helping enterprise customers translate AI capabilities into measurable business outcomes, drive adoption, and navigate meaningful workflow and process change.

In this highly visible leadership role, you will build the operating rhythm, coaching culture, and customer strategy that enables your team to deliver exceptional outcomes across a complex enterprise portfolio. You will partner closely with Sales, Product, Engineering, Marketing, and Professional Services to drive retention, expansion, and long-term customer value.

Key Responsibilities:

  • Lead and Develop AI Success Managers: Hire, coach, and develop a world-class team of Enterprise AI Success Managers. Create the tools, training, and career development needed for the team to excel in a rapidly evolving AI environment.
  • Drive Strategic Customer Outcomes: Guide your team in building trusted relationships with executive, operational, and technical stakeholders. Ensure customers have clear success frameworks, actionable plans, and measurable paths to value.
  • Lead at Enterprise Scale: Coach and support AI Success Managers as they manage multiple complex enterprise accounts simultaneously. This requires strong prioritization, operational discipline, resilience, and grit—helping customers navigate competing priorities while continuing to drive adoption, value realization, renewals, and expansion across the portfolio.
  • Scale AI Adoption and Value Realization: Help the team move customers from AI ideas to real-world impact—driving adoption, usage, workflow change, and measurable performance improvements through Cresta’s platform.
  • Coach for Product Expertise and Execution: Ensure AI Success Managers develop deep product fluency and the confidence to engage hands-on when needed, including guiding customers on product configuration, prompts, workflows, rules, and new capabilities.
  • Own Retention and Expansion: Lead the team’s strategy and execution around customer health, renewals, risk mitigation, and expansion. Partner with Sales to identify opportunities to deepen Cresta’s impact across accounts.
  • Establish Operational Excellence: Define, monitor, and improve key success metrics, including adoption, time-to-value, customer health, Gross Renewal Rate, and Net Dollar Retention. Use data to identify trends, prioritize action, and improve team performance.
  • Drive Cross-Functional Alignment: Partner closely with Sales, Product, Engineering, Marketing, and Professional Services to ensure a seamless customer experience and accelerate customer outcomes.
  • Champion the Voice of the Customer: Bring customer insights, challenges, and opportunities into the organization. Partner with Product and Engineering to influence priorities and help shape how Cresta continues to serve enterprise customers.

We’re Looking For Someone Who:

  • Has experience leading and developing Customer Success, Strategic Account Management, Consulting, or similarly customer-facing teams in a fast-paced SaaS, AI, or technology environment.
  • Brings a strong track record of driving retention, expansion, adoption, and measurable customer outcomes across enterprise accounts.
  • Has experience leading teams that manage a high-volume portfolio of complex enterprise customers, with the prioritization, grit, and operational rigor required to deliver meaningful outcomes at scale.
  • Understands how to coach a team to connect technical capabilities and product usage to real business results—not just feature adoption.
  • Is comfortable operating in a technical, AI-driven environment and can help their team build fluency in SaaS configuration, data analysis, AI tools, and evolving product capabilities.
  • Thinks strategically and systematically, with the ability to bring structure to ambiguity and translate insights into action.
  • Has exceptional executive communication skills and can build trust with customers and internal stakeholders at every level.
  • Is highly data-driven and able to use performance metrics to identify risks, coach teams, and improve customer outcomes.
  • Thrives in a high-growth environment where the product, customer needs, and best practices are evolving quickly.
  • Is willing to travel approximately 25% and work across time zones.

Perks & Benefits:

We offer a comprehensive and people-first benefits package to support you at work and in life:

  • Comprehensive medical, dental, and vision coverage with plans to fit you and your family
  • Flexible PTO to take the time you need, when you need it
  • Paid parental leave for all new parents welcoming a new child
  • Retirement savings plan to help you plan for the future
  • Remote work setup budget to help you create a productive home office
  • Monthly wellness and communication stipend to keep you connected and balanced
  • In-office meal program and commuter benefits provided for onsite employees

Compensation at Cresta:

Cresta’s approach to compensation is simple: recognize impact, reward excellence, and invest in our people. We offer competitive, location-based pay that reflects the market and what each individual brings to the table.

Base Salary Range: $180,000–$245,000 + Bonus + Equity

Actual base salaries will be based on candidate-specific factors, including experience, skill set, location, and applicable local minimum-pay requirements. Your recruiter can provide further details. In addition, total compensation includes a comprehensive benefits package for you and your family.


Our use of AI in recruiting: We may use AI tools in our recruiting process, which require human review and oversight. If you have questions about our use of AI or wish to opt out, please contact recruiting@cresta.ai (if you are opting out, please use the subject ‘Opt-Out’ in your email).

Recording & AI transcription: We do not authorize candidates to record or use AI transcription of any interview by phone, notetaker app, AI glasses, or other device. Candidates may request an exception or accommodation for review during the interview process as needed.

Recruiting impersonation scams: We have noticed a rise in recruiting impersonations across the industry, where scammers attempt to access candidates’ personal and financial information through fake interviews and offers. All Cresta recruiting email communications will always come from the @cresta.ai domain. Any outreach claiming to be from Cresta via other sources should be ignored.

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