[Hiring] Director of Enterprise AI Success @Cresta

Role Description

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.

Qualifications

• Experience leading and developing Customer Success, Strategic Account Management, Consulting, or similarly customer-facing teams in a fast-paced SaaS, AI, or technology environment.
• Strong track record of driving retention, expansion, adoption, and measurable customer outcomes across enterprise accounts.
• 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.
• Understanding of how to coach a team to connect technical capabilities and product usage to real business results—not just feature adoption.
• 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.
• Strategic and systematic thinker, with the ability to bring structure to ambiguity and translate insights into action.
• Exceptional executive communication skills and can build trust with customers and internal stakeholders at every level.
• 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.
• Willing to travel approximately 25% and work across time zones.

Benefits

• 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.