Head of Customer Success, Enterprise & Strategic
WFA Digital Insight
As demand for digital transformation specialists grew 27% in 2025, companies like Ramp are at the forefront of innovation. With a focus on finance teams, Ramp's customer success team drives real impact. To succeed in this role, candidates need a deep understanding of GTM strategies and Salesforce. Ramp stands out for its commitment to building systems that shape how companies manage billions. Before applying, candidates should be aware of the high stakes and fast-paced environment, requiring high agency and urgency.
Job Description
About the Role
The Head of Enterprise & Strategic Success is a senior leadership role that leads the customer success motion across Ramp's largest and most complex accounts. This role is 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.The ideal candidate will have a deep understanding of AI-augmented workflows and the ability to set the standard for how the CS org leverages AI for customer communication, data synthesis, account prioritization, and predictive engagement.
Ramp is building the smart infrastructure for finance teams, embedded in the transaction flow of every dollar a business spends. The company automates how over
What You Will Do
- Lead 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.
- 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.
- Partner with enterprise customers' executive stakeholders 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 integration.
- 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.
What We Are Looking For
- 8+ years of experience in customer success, with a focus on enterprise and strategic accounts.
- Proven track record of leading high-performing teams and driving customer growth.
- Deep understanding of GTM strategies and Salesforce.
- Experience with AI-augmented workflows and a clear point of view on where AI should replace, augment, or stay out of the customer experience.
- Strong communication and interpersonal skills, with the ability to build relationships with executive stakeholders.
- Experience with change management and transformation initiatives.
- Strong analytical and problem-solving skills, with the ability to drive data-driven decisions.
Nice to Have
- Experience with finance and accounting systems.
- Knowledge of cloud-based software and SaaS platforms.
- Certification in customer success or a related field.
Benefits and Perks
- Competitive salary and equity package.
- Comprehensive health, dental, and vision insurance.
- 401(k) matching program.
- Flexible PTO policy and remote work options.
- Professional development opportunities and access to industry events.
- Access to the latest tools and technologies, including Salesforce and AI-powered software.
How to Stand Out
- Tip: Highlight your experience with GTM strategies and Salesforce in your application, and be prepared to discuss how you've used these tools to drive customer growth.
- To stand out, focus on building a strong portfolio that showcases your customer success expertise and ability to lead high-performing teams.
- When interviewing, be prepared to discuss your experience with change management and transformation initiatives, and how you've driven data-driven decisions in previous roles.
- Be aware of the high stakes and fast-paced environment at Ramp, and be prepared to discuss how you handle pressure and urgency.
- Research the company culture and values, and be prepared to discuss how you align with Ramp's mission and vision.
- Don't be afraid to ask questions about the role and the company during the interview process - it shows that you're interested and engaged.
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