Head of Customer Success, Ramp

• 10+ years of experience in Customer Success, Account Management, or Post-Sales leadership, with at least 5 years in a senior leadership role managing enterprise or strategic accounts
• Proven experience leading change management and digital transformation initiatives within large multinational corporations—you’ve navigated the complexity of global rollouts, multi-entity structures, and executive stakeholder alignment
• Track record of building and scaling high-performing CS teams (20+ CSMs) with clear operating cadences, performance frameworks, and a culture of continuous improvement
• Deep expertise in enterprise activation metrics: spend activation, product adoption, time-to-value, net revenue retention, and customer health scoring
• Strong AI fluency—you actively use AI tools in your work, have a clear point of view on AI’s role in customer success, and can drive adoption of AI-augmented workflows across a team
• Exceptional executive presence and communication skills, with the ability to engage C-suite stakeholders at Fortune 500 companies and translate complex organizational dynamics into actionable CS strategies
• Experience in fintech, SaaS, or financial operations is strongly preferred; familiarity with corporate card, expense management, or procurement platforms is a plus
• Comfort operating in a high-growth, fast-moving environment where you’ll be building the playbook as you go—not inheriting a fully mature operation

Desirable

• 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
• 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
• 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
• 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 recognition
• Collaborate closely with Enterprise Sales, Solutions Engineering, and Partnerships to ensure seamless handoffs and a unified customer experience from pre-sale through long-term expansion
• Influence Product roadmap by synthesizing enterprise customer needs, competitive intelligence, and market trends into actionable insights for the Product team
• Build and maintain executive-level relationships across the customer portfolio, positioning Ramp as a strategic partner—not just a vendor—to the world’s largest organizations
• First 90 Days
• Complete a diagnostic of the current Enterprise & Strategic CS motion: team structure, account coverage model, health scoring, and activation metrics
• Build relationships with key enterprise customers and conduct listening tours with cross-functional stakeholders (Sales, Product, Partnerships)
• Identify the top 3–5 operational gaps and present a 6-month roadmap to the executive team with clear milestones and resource requirements
• Establish initial AI-augmented workflows for at least one core CS process (e.g., health scoring, account prioritization, or QBR preparation)
• By 6 Months
• Enterprise & Strategic activation rates are measurably improving, with a clear correlation to the new playbooks and operating cadences you’ve implemented
• The team has a defined change management framework for multinational rollouts, with at least 2–3 enterprise accounts actively using it
• AI fluency is embedded across the team: every CSM is using AI tools daily, and you’ve shipped at least two AI-augmented workflow improvements
• Cross-functional feedback loops with Product and Sales are formalized and producing actionable insights that influence the roadmap and GTM strategy
• You’ve built a talent strategy for the team—hiring plan, competency framework, and career development pathways are in place