Head of Customer Success

Why Legal On

Legal On is a global leader in AI for in-house legal teams. We help corporate counsel guide, govern, and grow their businesses with speed and sound judgement. By combining trusted legal expertise with agentic AI that adapts to each customer’s policies and practices, Legal On delivers the first productivity platform for everyday legal work across contracting, counseling, and governance.

Trusted by 7,500+ organizations worldwide and growing quickly, Legal On is backed by $200 million from leading investors, including Goldman Sachs and Soft Bank. With headquarters in San Francisco and Tokyo, and teams in London, Munich, and Singapore, Legal On supports businesses of all sizes, across industries and languages.

We are building the most trusted and beloved brand in legal technology, and we want ambitious and driven individuals to join us. If you are eager to grow your career through performance, capability, and impact, you will thrive at Legal On.

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.

Responsibilities

• 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

• Customer Onboarding & Engagement
- 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

• Renewals & Expansion
- 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

Qualifications

• 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

Benefits

• Competitive compensation and equity.

• Generous paid time off policies.

• Health, dental, and vision insurance.

• 401(k)

• Professional development opportunities.

#JLjbffr