Customer Strategy Director

About the Role

This is a senior individual contributor role on Cresta's Customer Strategy team, a small, high-impact group that operates at the intersection of AI strategy, contact center transformation, and enterprise sales. We show up as operators, not software vendors. Our job is to turn AI anxiety into AI confidence for the enterprises ready to lead the next era of customer experience.

You'll engage at the C-suite and executive level with Cresta's largest and most strategic accounts, acting as a trusted advisor who can make the value of AI concrete and stay accountable to real, measurable outcomes. You'll partner closely with Sales, Professional Services, and Customer Success, and serve as a thought leader both in customer engagements and internally across product, marketing, and GTM.

East or Central US strongly preferred. This role involves regular customer travel (1-2 days/week) and the majority of Cresta's largest strategic accounts are concentrated in the Eastern time zone.

What You'll Do

Vision & Thought Leadership

• Open strategic enterprise engagements with executive-level vision sessions, not pure product pitches, establishing Cresta's point of view on how AI will reshape contact center operations
• Help customers see where AI is taking their business, not just what's available today
• Represent Cresta at external events as a credible voice in AI and CX transformation

Strategic Customer Engagement

• Lead business value discovery, stakeholder alignment, and use-case scoping across complex, multi-stakeholder enterprise accounts
• Guide customers through operational readiness, change management, and deployment planning, including Center of Excellence models and governance structures
• Support pilot and Conversational Assessment design, goal-setting, and executive readouts
• Facilitate business case development as a collaborative exercise with the customer, rather than a Cresta-owned spreadsheet, so customers internalize and own the value story

Scope & Deal Strategy

• Partner with Sales to push deals toward full platform adoption where warranted, expanding beyond initial narrow use cases
• Advise on pricing strategy and business models for non-standard deal structures
• Own positioning and sale of professional services as part of a broader engagement strategy

Internal Contribution

• Serve as voice of the customer for Product, Marketing, and Partner teams
• Build repeatable playbooks, frameworks, and executive assets that scale the team's approach across the Enterprise segment
• Help Cresta stay ahead of AI trends and their implications for customers and our own GTM

What We're Looking For

• Deep credibility in AI agents: you understand the technology, its current limitations, and the competitive landscape well enough to advise customers making real transformation decisions
• Contact center domain expertise, whether from operating inside one or selling into them at enterprise scale
• Exceptional executive presence and storytelling ability; you can hold a C-suite room, make complex AI strategy legible, and leave customers with conviction, not just information
• A visionary orientation; customers are anxious about AI and overwhelmed with options, you're the person who gives them clarity and a path forward
• Strong product and technical fluency; PM background is a strong signal, you need to engage credibly on integration tradeoffs, deployment architecture, and model behavior without necessarily being an engineer
• Proven experience leading large, complex enterprise engagements with multiple stakeholders and long sales cycles
• Comfort with an IC role and a high-travel cadence; this is not a team management position, the leverage comes from depth of customer engagement