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
Drive Change & Transformation Management
Operationalize & Scale with AI
Cross-Functional Leadership
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
By 6 Months
100% medical, dental & vision insurance coverage for you
Partially covered for your dependents
One Medical annual membership
401k (including employer match on contributions made while employed by Ramp)
Flexible PTO
Fertility HRA (up to $10,000 per year)
Parental Leave
Unlimited AI token usage
Pet insurance
Centralized home-office equipment ordering for all employees
Health and Wellness stipend
In-office perks: lunch, snacks, drinks, and more
Budget for intra-office travel
Relocation support to NYC or SF (as needed)
If you are being referred for the role, please contact that person to apply on your behalf.
Pursuant to the San Francisco Fair Chance Ordinance, we will consider for employment qualified applicants with arrest and conviction records.
Beware of recruiting scams: Ramp will only contact you through official @ Ramp.com email addresses and will never ask for payment or sensitive personal information during the hiring process.
Ramp Applicant Privacy Notice