Head of Customer Success

Role Overview

We are seeking a Head of Customer Success to lead and scale our Customer Success function. Reporting directly to the CEO, this role will own the end-to-end customer lifecycle—from onboarding and engagement through renewals and expansion.

You will manage and grow a team of Customer Success professionals, partner closely with Sales, Marketing, Product, and Legal experts, and play a critical role in driving customer retention, satisfaction, and revenue growth. This is a highly visible leadership role with direct impact on company performance.

• Customer Success Strategy and Leadership
• Define and execute Legal On’s customer success strategy to drive adoption, retention, renewals, and expansion
• Lead, mentor, and grow a high-performing Customer Success team (currently 5+ members)
• Establish clear goals, success metrics (e.g., NRR, churn, product adoption), and operating rhythms
• Own and continuously improve the customer onboarding experience to ensure fast time-to-value
• Design engagement models tailored to different customer segments (SMB, mid-market, enterprise)
• Partner with Product to incorporate customer feedback into roadmap and feature prioritization
• Play a critical role in driving renewals and identifying expansion opportunities in partnership with Sales
• Develop proactive strategies to mitigate churn and increase customer lifetime value
• Support executive-level customer relationships and strategic accounts as needed
• Cross-Functional Collaboration
• Collaborate with Legal experts and other internal stakeholders who also support customers to deliver a seamless, high-quality customer experience
• Partner with Marketing on customer advocacy, case studies, trainings, and community initiatives
• Work closely with Sales on handoffs, renewals, and expansion strategy
• Operational Excellence
• Ensure Customer Success operations scale effectively as the company grows globally
• Track and report on customer health, performance, and key insights to executive leadership
• Build scalable processes, playbooks, and tooling to support growth

• 8+ years of experience in Customer Success, Account Management, or related roles in a B2B SaaS environment
• Proven experience hiring, retaining, and leading high performance Customer Success teams
• Strong track record of driving renewals, retention, and expansion
• Experience working cross-functionally with Sales, Marketing, Product, and executive leadership
• Excellent communication, leadership, and stakeholder management skills
• Data-driven mindset with experience using customer success metrics and tools
• You have a bias for action and are relentlessly resourceful – able to get things done despite constraints, roadblocks, and setbacks
• Preferred
• Experience in legal tech or serving in-house legal teams
• JD and experience as an attorney
• Experience working with global customers or scaling CS functions internationally
• While we are open to candidates located anywhere in the United States, we prefer candidates excited to work in office 1-2 days per week in San Francisco