Regional Director, AI Deployment

Regional Director, AI Deployment

Our mission is to automate coding. The first step in our journey is to build the best tool for professional programmers, using a combination of inventive research, design, and engineering. Our organization is very flat, and our team is small and talent dense. We particularly like people who are truth-seeking, passionate, and creative. We enjoy spirited debate, crazy ideas, and shipping code.

About the Role

As Regional Director, AI Deployment at Cursor, you'll lead and develop a team of AI Deployment Managers supporting some of our most strategic enterprise customers. This role exists to scale adoption quality and consistency as demand accelerates — translating Cursor's momentum into repeatable, high-impact deployment outcomes while preserving the speed, flexibility, and developer-first ethos that make Cursor successful. You'll own the post-sale experience for our enterprise segment, working closely with Sales and Field Engineering to ensure customers achieve measurable engineering and business value from Cursor. This is a highly cross-functional role that sits at the intersection of customer success, technical depth, and strategic leadership.

What You'll Do

• Hire, lead, and develop a team of AI Deployment — including onboarding, coaching, performance management, and ongoing skill development
• Own post-sale account planning, with accountability for account health, usage, risk mitigation, and expansion pipeline generation
• Act as an escalation point for complex deployments and high-stakes enterprise accounts
• Build lightweight, scalable processes that codify what works while preserving speed, flexibility, and low friction
• Guide best practices around rollout strategy, prompt design, context configuration, and internal enablement
• Partner closely with Sales and Field Engineering to deliver a seamless post-sale experience and support expansion opportunities
• Collaborate with Product, Engineering, and Marketing to advocate for customer needs, influence roadmap priorities, and drive product adoption

You May Be a Fit If

• You have 4+ years of experience leading customer-facing technical teams in TAM, Solutions, Deployment, or similar roles
• You have a strong understanding of software development lifecycles, engineering org structures, and AI-enabled developer tooling
• You have a proven track record of driving adoption and influencing expansion through customer outcomes
• You have executive presence and strong communication skills — comfortable whiteboarding with developers and discussing business value with VP- and CTO-level stakeholders
• You're a high-agency, scrappy operator who thrives in fast-moving, ambiguous environments
• You care deeply about AI and believe that transforming how software is written is one of the most important problems to work on right now