Senior Customer Success Manager (Legal)

Senior Customer Success Manager

Full-time, Hybrid, New York (or Remote/USA for the right candidate)

The Company

Checkbox is a Sequoia-backed software company building the AI Legal Front Door for in-house legal teams. General Counsels and Legal Operations use Checkbox to redefine how legal work enters, flows through, and gets resolved inside enterprise companies. Our customers today are the in-house legal departments from companies like SAP, Hitachi, and Pepsi.

Support teams had Zendesk. Sales had Salesforce. IT had ServiceNow. Each became the defining system of record and engagement for their function, enabling new levels of scale, visibility, and impact. But more than that, each system fundamentally redefined how the function operated. Each of these business functions had its moment of transformation. And legal is next.

Until now, legal has been the last major business function without its own purpose-built platform to orchestrate workflows, manage service delivery, and demonstrate value to the business. This is what we’re building at Checkbox – AI-powered Service Management for in-house legal teams.

As a company, we are a passionate and ambitious team of 70+ people across the United States, Australia, and Asia, made up of high performers and Co-Founders in the Forbes 30 Under 30 list. Our culture is one of our superpowers. It's what people talk about when they join us, work with us, and leave us.

Read about what makes all of us a "Checkmate" here:

The Position

At Checkbox, we set a high bar for customer experience. It’s what we are known for, what we celebrate internally, and a core driver of our success. Our customers choose us not only for category-defining technology, but for a team that delivers measurable outcomes and sustained impact across their legal function. That standard shapes how we hire, how we operate, and how we partner.

As a Senior Customer Success Manager, you will partner with enterprise legal teams to ensure they realize meaningful business outcomes with Checkbox. Ideally, you bring prior experience working with legal tech platforms or supporting legal and legal operations teams, allowing you to quickly understand the workflows and challenges faced by in-house legal departments.

In this role, 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.

You will work closely with Legal Engineers, Onboarding and Product teams to drive adoption, identify opportunities for growth and ensure customers continue to realize increasing value from their investment in Checkbox.

Outcomes you will drive in this role

Account Ownership

• Take ownership of enterprise customers as they transition from onboarding toward go-live, ensuring a smooth handoff and continuity in the customer journey.

Customer Adoption & Operational Impact

• Ensure customers successfully embed Checkbox into their legal workflows after go-live, helping legal teams transition from initial deployment to meaningful operational impact across their organization.

Long-Term Customer Partnerships

• Build trusted relationships with stakeholders across legal, operations and business teams, positioning Checkbox as a strategic platform within their legal operations ecosystem.

Account Growth & Expansion

• Identify and drive opportunities to expand Checkbox usage by introducing new workflows, departments and use cases that increase the platform’s value across the organization.

Customer Retention & Renewals

• Own the retention and renewal of your portfolio of enterprise customers by ensuring continued alignment between customer goals and the outcomes delivered through Checkbox.

Strategic Customer Engagement

• Lead strategic conversations with customers through regular check-ins, business reviews, roadmap discussions and workflow optimization sessions.

Customer Insights & Product Influence

• Capture structured feedback and usage insights from customers and partner with Product and Engineering to inform roadmap priorities and improve the platform.

Customer Advocacy

• Drive advocacy initiatives including customer success stories, reviews and testimonials that showcase the impact of Checkbox across customer organizations.

Data-Driven Account Management

• Leverage data and customer insights to monitor account health, identify risks and growth opportunities and guide proactive engagement strategies.

Complex Issue Leadership

• Lead the resolution of complex customer challenges by coordinating with internal teams and ensuring timely, effective outcomes for customers.

About you

• 5-7 years of experience in customer success or account management, with a proven track record of managing large, complex enterprise accounts and delivering results.

• Experience working in legal technology or supporting legal and legal operations teams is strongly preferred. You understand the workflows, stakeholders and operational challenges faced by in-house legal departments.

• Ability to think strategically and see the big picture, while also being detail-oriented and hands-on in execution. Your ability to connect customer goals with product capabilities allows you to guide customers toward meaningful outcomes.

• A strong understanding of SaaS products and experience working closely with technical teams to deliver tailored solutions for customers. Experience with legal tech, workflow automation, or no-code platforms is a plus.

• A relentless focus on customer success, with the ability to build and sustain trusted, long-term relationships with stakeholders across customer organizations.

• Bring a strong commercial mindset to customer engagement. You are comfortable identifying expansion opportunities, leading upsell conversations, and managing renewals to drive long-term account growth.

• Excellent interpersonal and communication skills, with the ability to confidently lead complex discussions, workshops and executive-level conversations with both technical and non-technical stakeholders.

• Comfortable working in a fast-paced, high-growth environment, managing multiple priorities and navigating ambiguity with confidence.

• A results-driven mindset with a strong track record of improving customer outcomes and driving key success metrics such as adoption, retention, expansion, NPS and overall account health.

Benefits

• 20 days PTO per year, with rollover of unused leave (paid out upon leaving the company)

• 11 days paid Federal holidays per year

• Paid parental leave (primary and secondary)

• Health insurance, including dental and vision coverage

• 401K retirement savings match

• Fully paid annual trips to company offsites (past destinations include Australia, Bali, South Korea)