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

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.

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