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Checkbox is a Series A B2B legal technology company building foundational tools for enterprise legal teams to manage and resolve legal work at scale. The platform combines modern SaaS workflow tooling with agentic AI-native product experiences, helping legal teams capture, triage, route, manage and complete work with greater visibility, speed and control.
As a Senior Customer Success Manager, you will partner with enterprise legal teams to ensure they realize meaningful business outcomes with Checkbox. You will guide customers from initial adoption through long-term growth, helping them embed Checkbox into their legal workflows and achieve measurable operational impact. You will own the health, retention and expansion of a portfolio of enterprise customers.
Key responsibilities include: taking ownership of enterprise customers as they transition from onboarding toward go-live; ensuring customers successfully embed Checkbox into their legal workflows and achieve operational impact; building trusted relationships with stakeholders across legal, operations and business teams; identifying and driving expansion opportunities by introducing new workflows, departments and use cases; owning retention and renewals of your customer portfolio; leading strategic conversations through regular check-ins, business reviews and roadmap discussions; capturing structured feedback and usage insights to inform product roadmap priorities; driving customer advocacy initiatives including success stories and testimonials; leveraging data to monitor account health and identify risks and growth opportunities; and leading resolution of complex customer challenges by coordinating with internal teams.
You bring 5+ years of experience in customer success or account management with a proven track record managing large, complex enterprise accounts. Experience working in legal technology or supporting legal and legal operations teams is strongly preferred. You think strategically while remaining detail-oriented and hands-on. You have strong understanding of SaaS products and experience working closely with technical teams. You bring a relentless focus on customer success, ability to build trusted long-term relationships, and a strong commercial mindset comfortable identifying expansion opportunities and managing renewals. You have excellent interpersonal and communication skills, can confidently lead complex discussions and executive-level conversations, and thrive in fast-paced, high-growth environments managing multiple priorities.
