RVP, Digital CSM

Triwill Group; San Francisco (CA); On-site; USD 180,000 - 240,000; Full time

Job summary

Cursor is seeking an RVP, Customer Success - Digital to design and lead the digital CS function for a large self-serve user base. You’ll build the scaled, tech-touch motion that drives adoption, retention, and expansion while preserving the developer-first ethos that defines Cursor.

Reporting to the SVP, Customer Success, you’ll own activations, onboarding, health signals, and AI-powered plays, partnering with Product, Growth, RevOps, and Sales to deliver a seamless, product-led growth engine at

Responsibilities

• Build the digital CS motion from the ground up: design the operating model for scaled, one-to-many coverage - pooled CSMs managing large books through tooling and automation rather than 1:1 relationships.
• Own activation & onboarding: ship self-serve onboarding, lifecycle communications, and in-product nudges that reliably get customers to first value with no manual touch.
• Own scaled retention and expansion: accountable for adoption, health, GRR/NRR, and product-led expansion across the self-serve and usage-based segment.
• Stand up automated, signal-driven engagement: health scoring and usage signals (seat utilization, blocked users, MAU/token trends) that trigger outreach without a human watching every account; behavior-based lifecycle plays (e.g. a user hits a rate limit automated play fires); in-app nudges and product-led expansion motions.
• Use AI as a force multiplier: build AI-powered engagement plays that extend a small team's reach, and partner with Product to clarify what this team builds vs. what belongs in the product itself.
• Instrument and operate by data: define what "activated" and "healthy" mean per tier, partner with RevOps/Data to build the health-scoring and reporting backbone, and run a rigorous experimentation program that separates real behavior change from surface activity.
• Build community as a scale layer: Slack/forum communities and self-serve resources as a scalable engagement and support channel.
• Partner cross-functionally: work with Product & Engineering, Growth/PLG, Marketing, RevOps, Sales, and the other RVPs to deliver a seamless scaled experience and unlock expansion.
• Hire, lead, and develop leaders: build and coach a team of Regional Directors (Named + Pooled) and their CSMs, including onboarding, performance management, and career growth.

Job description

Description: 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

We're hiring an RVP, Customer Success - Digital to build and lead Cursor's digital customer success function, the scaled, tech-touch motion that drives adoption, retention, and expansion across our large self-serve and usage-based customer base. This role exists to capture that opportunity: turning Cursor's product-led momentum into repeatable, one-to-many success and expansion outcomes, without scaling headcount linearly, while preserving the speed, flexibility, and developer-first ethos that make Cursor successful.

You’ll be the founding leader of this function, reporting to the SVP, Customer Success, and you’ll own the systems, signals, and playbooks that make scaled success work. We're deliberately not handing you a playbook.

What you'll do

• Build the digital CS motion from the ground up: design the operating model for scaled, one-to-many coverage - pooled CSMs managing large books through tooling and automation rather than 1:1 relationships.
• Own activation & onboarding: ship self-serve onboarding, lifecycle communications, and in-product nudges that reliably get customers to first value with no manual touch.
• Own scaled retention and expansion: accountable for adoption, health, GRR/NRR, and product-led expansion across the self-serve and usage-based segment.
• Stand up automated, signal-driven engagement: health scoring and usage signals (seat utilization, blocked users, MAU/token trends) that trigger outreach without a human watching every account; behavior-based lifecycle plays (e.g. a user hits a rate limit automated play fires); in-app nudges and product-led expansion motions.
• Use AI as a force multiplier: build AI-powered engagement plays that extend a small team's reach, and partner with Product to clarify what this team builds vs. what belongs in the product itself.
• Instrument and operate by data: define what "activated" and "healthy" mean per tier, partner with RevOps/Data to build the health-scoring and reporting backbone, and run a rigorous experimentation program that separates real behavior change from surface activity.
• Build community as a scale layer: Slack/forum communities and self-serve resources as a scalable engagement and support channel.
• Partner cross-functionally: work with Product & Engineering, Growth/PLG, Marketing, RevOps, Sales, and the other RVPs to deliver a seamless scaled experience and unlock expansion.
• Hire, lead, and develop leaders: build and coach a team of Regional Directors (Named + Pooled) and their CSMs, including onboarding, performance management, and career growth.

You may be a fit if

• Built or scaled a digital / tech-touch / one-to-many customer success function - pooled coverage, automation- and lifecycle-driven, serving a large customer base.
• Developer-tools / technical-software domain experience - credibility with a developer/technical audience and their buying/adoption patterns.
• Leader of leaders: proven experience hiring, developing, and managing managers/directors at scale, with a high talent bar.
• Fluency with the scaled-CS toolkit: health-scoring design, usage-based signals, CS/automation tooling, and PLG expansion motions; comfortable owning GRR/NRR.
• Strong understanding of software development lifecycles, engineering org structures, and AI-enabled developer tooling.
• Executive presence and communication - credible with developers and with VP/CTO/CFO-level stakeholders on value.
• High-agency, scrappy operator who thrives in fast-moving, ambiguous, high-growth environments and builds in motion.