Head of Customer Success

Glassbox is seeking a proven Customer Success leader to build and lead a new team of Strategic CSMs supporting our largest and most complex North American customers. These accounts are primarily top-tier financial institutions with ARR typically ranging from $500K to more than $2M per customer.

In this role, you will redesign the Customer Success operating model, establish processes and playbooks, and enable your team to deliver measurable value, strong renewal readiness, and referenceable customer outcomes. You will manage a team of hands-on, insights-driven CSMs to ensure customers realize the full value of Glassbox across their digital journeys. You will build executive alignment and enable your team members to surface insights that strengthen adoption and long-term partnership. 

This is a strategic, high-visibility role for a leader who understands enterprise digital experience analytics, has experience working with large financial institutions, and excels at building scalable CS programs from the ground up.

Key Responsibilities

• Lead, coach, and develop a team of CSMs covering Glassbox’s large enterprise customers, ensuring renewal readiness and willingness to expand.
• Build the Customer Success operating model, including processes, playbooks, metrics, and team standards.
• Manage 1-2 customers hands-on to experience challenges firsthand and demonstrate leadership by example.
• Create templates for adoption planning, covering goals, success metrics, and action plans.
• Provide guidelines for identifying business units that would see value from Glassbox and potential champions.
• Build tools for data-driven analysis of product usage across the enterprise business units.
• Curate a repository of recommendations for expanding usage across additional journeys and teams.
• Define cadences for regular check-ins, QBRs, and executive business reviews.
• Establish a consistent approach to value realization, providing clear evidence of business impact.
• Fine-tune the risk identification methodology, providing early warning and accurate predictions.
• Work closely with other teams to scope and deliver technical and consulting services to the customers.
• Partner with the account management team to support the renewal process and identify opportunities for expansion.
• Escalate customer issues quickly and coordinate resolution with key managers across the organization.
• Represent Customer Success in cross-functional planning and management meetings.
• Support the implementation and use of a Customer Success platform for account health & workflow management.
• Develop referenceable customers by showcasing success stories and ensuring high-quality experiences.
• Partner with leadership to refine segmentation, coverage models, and resource allocation for strategic accounts.
• Provide input into product roadmap priorities based on customer feedback and industry needs.

Qualifications

• 8+ yrs experience in Customer Success for enterprise SaaS solutions.
• 3+ years of proven success managing Customer Success teams supporting enterprise customers.
• Experience working with banking customers and other highly regulated industries.
• Deep familiarity with digital experience analytics, UX optimization, and data-driven SaaS products.
• Experience building Customer Success processes, playbooks, operating models, and team standards.
• Strong ability to interpret data and translate into business recommendations.
• Demonstrated skill engaging C-suite and VP-level executives at large, complex organizations.
• Experience partnering closely with Account Management, Services, Support, and Product organizations.
• Hands-on expertise with CS and CRM tools - experience onboarding a CS platform is a plus.
• Strong communication, executive presence, and storytelling skills.
• AI fluency and comfort using AI-enabled tools and workflows are referred.
• Bachelor’s degree or equivalent - advanced degree is a plus.