Senior Customer Success Manager (Legal)

Checkbox Technology • New York, NY

42d • Hybrid

About 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.

Requirements

• 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.

Nice To Haves

• Experience with legal tech, workflow automation, or no-code platforms is a plus.

Responsibilities

• Account Ownership
• Customer Adoption & Operational Impact
• Long-Term Customer Partnerships
• Account Growth & Expansion
• Customer Retention & Renewals
• Strategic Customer Engagement
• Customer Insights & Product Influence
• Customer Advocacy
• Data-Driven Account Management
• Complex Issue Leadership

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)

What This Job Offers

• Job Type: Full-time
• Career Level: Mid Level
• Education Level: No Education Listed
• Number of Employees: 11-50 employees