TITLE: HEAD OF CUSTOMER SUCCESS

Location: New York or SF Bay Area preferred. Remote in USA Tier 1 city
Reports to: CEO

REQUIREMENTS

• 8+ years in customer success or post-sales leadership, with 4+ years managing enterprise CS teams at an Enterprise SaaS company with ACV over $200K
• At a minimum, managed 5+ CSMs or AEs responsible for post-sales
• Total Book Value (Managed ARR): minimum $10M ARR under team
• Direct experience managing accounts with ACV over $500K in high-touch motion
• Direct experience with enterprise sales cycles, especially pilot or POC-based land and expand motions
• Develop and operationalize data-driven playbooks and processes for onboarding, adoption/utilization, POC conversion, and expansion—anchored in clear KPIs such as time-to-value, NRR, pilot conversion rate, and account expansion velocity.
• Excellent executive presence, relationship building, communication, and value-selling capability
• Direct experience working cross-functionally with both Pre-sales and Training/User Enablement
• Experience building CS function from scratch in a high-growth environment
• Operationally rigorous with a bias for solution and experimentation
• Interest in fashion/retail clients
• Early stage or late stage startup experience

ABOUT THE ROLE

We’re looking for a strategic and execution-driven Head of Customer Success to lead post-sales for our most important segment: enterprise customers. This is a pivotal role responsible for owning the pilot-to-expansion funnel, increasing conversion from pilot to multi-year contracts, and driving long-term account value.
You will be hands-on in working directly with our top enterprise customers, setting the bar for excellence in customer engagement and success. This role requires someone who can dive into the weeds, while also building and scaling repeatable processes.
You’ll help lead and grow the CSM team, setting clear goals and KPIs across conversion, revenue expansion, retention, and customer health. You’ll serve as both a strategic leader and coach—hiring and mentoring a high-performing team of CSMs and establishing a strong customer-centric culture. You’ll also work cross-functionally with Sales, Product, and Marketing to surface customer insights and inform roadmap, messaging, and growth strategy.