Head of Customer Success

Title: Head of Customer Success

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

Raspberry AI is a leading provider of industry-defining AI design software for fashion brands and retailers. Our software empowers brands to rapidly understand consumer demand and create unique designs within minutes. Leveraging cutting-edge AI analytics and generative AI capabilities, we help fashion brands revolutionize their design and merchandising processes.

We are a Series A startup, backed by top-tier venture capital firms such as Andreessen Horowitz, Khosla Ventures, MVP and Greycroft.

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.

Customer Success Strategy

• Design and own our enterprise customer journey, from pilots to multi-year expansion

• Drive segmentation strategy for enterprise accounts to tailor engagement models by customer type, maturity, and strategic value.

• Build playbooks to maximize pilot conversion, value realization, onboarding, user engagement, and user adoption

• Establish strong relationships across executive sponsors, mid-level stakeholders, and user populations across enterprise clients

POC Conversion & Expansion

• Own pilot success plans and develop frameworks to consistently convert pilots into contracts

• Partner with Sales to shape deal structure and success metrics pre-sale

• Develop and track leading indicators of expansion potential across accounts, enabling early upsell motions.

• Lead quarterly business reviews (QBRs), executive alignment, and value storytelling

Team Leadership

• Build and lead a world-class CS team across customer success managers, solution architects, and training/support

• Implement team-wide rituals for knowledge sharing, deal retros, and continuous improvement across CS team

• Recruit, coach, and develop a high-performing team that thrives in technical and enterprise environments

Cross-functional Execution

• Serve as the voice of the customer to Product and Engineering teams, influencing roadmap based on enterprise needs

• Collaborate with Marketing on customer references, case studies, and product education

• Partner with Sales to track usage data, health scores, and renewal signals
  

• 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

Nice to have

• Strong familiarity with generative AI tools

• Previous experience with fashion/retail clients

• Previous background managing creative stakeholders (design, marketing, ecommerce)

• Experience managing technical stakeholders, including innovation and IT teams