Head of Enterprise & Strategic Activations (Customer Success)

About Ramp Ramp is building the smart infrastructure for finance teams, embedded in the transaction flow of every dollar a business spends. We automate how over $200B in annualized spend flows in and out of 70,000+ companies: authorizing payments, flagging risk, categorizing spend, and closing books. The problems are high-stakes, data-dense, and unforgiving. We hire people with high agency and high urgency. We look for slope over intercept. We care less about where you trained and more about what you’ve built. At Ramp, everyone is a builder who owns problems end to end and makes consequential decisions that shape the outcome. The median Ramp customer saves 5% and grows revenue 16% in their first year – far in excess of businesses operating without Ramp. We believe every ambitious company deserves the same. If you want to build systems that directly shape how companies move and manage billions, Ramp is the place to do it. About the Role Ramp is the fastest-growing corporate card and spend management platform in America. Our Customer Success team is the driving force behind how the world’s most ambitious companies unlock the full power of Ramp’s platform to transform their financial operations. We’re looking for a Head of Enterprise & Strategic Success to lead our Customer Success motion across Ramp’s largest and most complex accounts—enterprise organizations and strategic partnerships with large multinational corporations. This is a senior leadership role responsible for building and executing the activation strategy that drives spend adoption, deepens product penetration, and accelerates time-to-value for accounts where organizational complexity, global footprint, and change management are defining challenges. You will own the customer journey for our highest-value segment, leading a team of CSMs who manage enterprise and strategic accounts through onboarding and activation across multiple products on the Ramp platform. You will be a thought partner to Sales, Product, and Partnerships leadership, ensuring that our post-sale experience matches the sophistication of our go-to-market motion. This role requires a leader who is deeply fluent in AI-augmented workflows: someone who doesn’t just adopt AI tooling, but has a clear point of view on where AI should replace, augment, or stay out of the customer experience. You will set the standard for how the CS org leverages AI for customer communication, data synthesis, account prioritization, and predictive engagement—driving efficiency gains while maintaining the high-touch, consultative relationships our enterprise customers expect. What You'll Do Lead Enterprise & Strategic Customer Success - Own the end-to-end customer success strategy for Ramp’s Enterprise and Strategic segments, setting the vision for how we activate, retain, and expand our largest accounts. - Build, lead, and develop a high-performing team of Enterprise CSMs, establishing a culture of accountability, intellectual curiosity, and customer obsession. - Define and drive the key metrics for the segment: spend activation rate, product adoption rate, time-to-value, net revenue retention, and customer health scores. Other metrics could include CSM-sourced leads and multiple-product attach rates. - Serve as the executive sponsor and escalation point for Ramp’s most complex and highest-value customer relationships. Drive Change & Transformation Management - Design and lead change management frameworks tailored to large multinational corporations undergoing financial operations transformation, including agentic workflows, with Ramp. - Partner with enterprise customers’ executive stakeholders (CFOs, VPs of Finance, Procurement leaders) to build adoption roadmaps that account for organizational complexity, regional variance, and multi-entity structures. - Develop playbooks for navigating the unique challenges of enterprise activation: multi-stakeholder alignment, global rollout sequencing, compliance requirements, and legacy system migration. - Bring a transformation management lens to every engagement—ensuring that Ramp is not just a tool adoption, but a catalyst for how enterprises rethink their financial operations. Operationalize & Scale with AI - Build AI-augmented workflows across the enterprise CS motion—from AI-driven health scoring and predictive analytics to automated customer communication and just-in-time product enablement. - Develop a clear framework for where AI should handle, assist, or defer to human CSMs across the customer lifecycle, ensuring the right balance of efficiency and high-touch service. - Champion AI fluency across the team: set the expectation that every CSM actively uses AI tools in their day-to-day work and maintains a point of view on how AI is reshaping customer success. - Partner with Product and Engineering to build feedback loops that translate enterprise customer insights into platform improvements, powered by data synthesis and AI-driven pattern recogn