Director of Customer Success

SimpleDocs is a fast-growing Legal AI software company helping global in-house legal teams modernize how they manage contracts. Our award-winning platform combines AI-powered contract review, drafting, workflow automation, and contract lifecycle management into a unified solution.

We are looking for a Director of Customer Success to lead the next stage of our customer experience. SimpleDocs already has established Sales, Legal Engineering, and Technical Implementation leadership. We now need a leader to define and execute the customer success strategy from post-sale transition through adoption, expansion, and renewal.

You will be responsible for helping hundreds of enterprise customers achieve measurable value from our products. Working closely with Sales, Technical Implementation, Legal Engineering, and Product, you will create consistent customer engagement practices, build strong relationships with legal and business stakeholders, and ensure customers continue to see value as their needs evolve.

This is a player-coach role. You will lead and develop an existing team while directly managing a portfolio of accounts, including strategic relationships. As the business grows, you will help shape the team, processes, and systems required to scale. Success will be measured primarily by customer satisfaction, retention, and expansion.

• Own the post-sale customer lifecycle. Establish a clear, repeatable approach to handoffs, success planning, onboarding coordination, adoption, business reviews, renewal preparation, and growth.
• Lead customer relationships. Act as a trusted partner to general counsel, legal operations leaders, and other senior stakeholders, connecting product capabilities to business outcomes.
• Drive retention and expansion. Monitor account health, identify risks early, develop recovery plans, and work with Sales to uncover and advance additional product and usage opportunities.
• Manage a portfolio of accounts. Personally own selected enterprise customers, model excellent account management, and remain close to day-to-day customer needs.
• Build and coach the team. Set priorities, clarify account ownership, establish engagement standards, and develop customer success managers as the organization grows.
• Partner across functions. Work with Technical Implementation and Legal Engineering to ensure successful deployments and transitions; collaborate with Sales on commercial opportunities and renewals; and bring structured customer feedback to Product and Engineering.
• Establish operating discipline. Introduce practical customer health scoring, segmentation, success plans, account reviews, renewal forecasting, and reporting that can scale across hundreds of customers.
• Improve adoption and value realization. Develop engagement and education programs that help customers increase utilization across SimpleAI, Repository, Workflow, and the broader platform.

• Retention: gross and net revenue retention, renewal rates, and reduction in preventable churn.
• Expansion: growth within existing accounts, product adoption, and qualified expansion opportunities developed with Sales.
• Customer satisfaction: customer feedback, relationship quality, and measurable improvements in customer experience.
• Execution: healthy account coverage, proactive risk management, successful post-implementation transitions, and reliable renewal visibility.

• 7+ years of experience in B2B customer success or strategic account management at a SaaS company, including meaningful experience managing enterprise customers.
• Demonstrated success improving retention, driving expansion, and managing renewal and account-health programs.
• Experience leading and coaching customer-facing teams, combined with a willingness to manage accounts directly.
• Ability to build credible relationships with senior customer stakeholders and navigate complex, multi-stakeholder organizations.
• Strong commercial judgment, data fluency, and experience working in close partnership with Sales and technical delivery teams.
• A practical, hands-on approach to building repeatable processes in a fast-growing company.
• Clear communication, sound judgment, and comfort learning sophisticated products and customer workflows.
• Experience in legal technology, CLM, enterprise workflow software, or AI-enabled products is helpful but not required.

• Help shape the customer experience at a fast growing Legal AI company serving hundreds of in-house legal teams around the world.
• Work with an established Sales and Implementation organization, strong technical and legal expertise, and a broadening product portfolio.
• Join a fully remote team of approximately 40 employees worldwide, with hubs in Mexico, California, the UK, and Cyprus.
• Make a direct impact on customer outcomes, recurring revenue, and the next stage of the company's growth.