Head of Customer Success, Enterprise & Strategic

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 recognition.

Cross-Functional Leadership

• 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.

What You Need

• 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.

Nice to Have

• Experience with management consulting or professional services delivery for enterprise accounts.
• Background in organizational change management methodologies (e.g., Prosci, Kotter, ADKAR) applied in a technology adoption context.
• Experience building or leading customer success for a category-creating product—where you had to define what “success” looks like for customers, not just optimize an existing motion.
• Familiarity with Gong, Salesforce, or similar platforms for call coaching, pipeline management, and customer intelligence.