Head of Customer Success, Enterprise & Strategic

Ramp is building the smart infrastructure for finance teams, embedded in the transaction flow of every dollar a business spends. We automate how over $100B in annualized spend flows in and out of 50,000+ 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.

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.

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.

• 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.

• 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.

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.

• Flexible PTO

• Unlimited AI token usage

• Centralized home-office equipment ordering

• Health and wellness stipend

• Budget for intra-office travel

• Weekly coffee stipend

• 100% medical, dental & vision insurance coverage for you, with partial coverage for dependents

• One Medical annual membership

• 401(k), including employer match on contributions made while employed by Ramp

• Fertility HRA (up to $10,000 per year)

• Parental leave: up to 16 weeks (80 days) at 100% pay

• Pet insurance

• In-office perks: lunch, snacks, drinks, and more

• Relocation support to NYC or SF (as needed)

• Group medical, dental, and vision coverage through Sun Life

• Life, AD&D, and disability coverage

• Fertility drug coverage (up to $4,000 lifetime)

• Group Retirement Plan with employer match (RRSP + DPSP)

• Parental leave: up to 16 weeks (80 days) at 100% pay, with additional time available at reduced pay

• Employee Assistance Program and virtual care through Lumino Health

• Private medical insurance through Freedom Elite

• Virtual GP and at-home care via eMed x Livi

• Workplace pension through Penfold, with salary sacrifice option

• Parental leave: up to 16 weeks (80 days) at 100% pay, with additional time available at reduced pay

If you are being referred for the role, please contact that person to apply on your behalf.

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