# Head of Customer Success, Enterprise & Strategic

**Company:** [Ramp](https://hotfix.jobs/companies/ramp)
**Location:** New York, NY, San Francisco, CA
**Role:** Customer Success
**Salary:** $261k – $358k/yr
**Experience:** 10+ years
**Skills:** AI, Salesforce, Gong, Change Management, Net Revenue Retention, Customer Health Scoring, Predictive Analytics, SaaS, Fintech, Digital Transformation
**Posted:** 2026-04-13

> Leads Customer Success for enterprise and strategic accounts, building AI-augmented workflows, driving activation metrics like spend adoption and NRR, and managing a team of CSMs through complex global transformations. Requires 10+ years experience with 5+ in senior leadership, AI fluency, and fintech/SaaS background.

## Job Description

## 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.

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