Managing Chief Counsel

General Counsel Full-time | United States (New York, Hybrid)

Be one of the first applicants, read the complete overview of the role below, then send your application for consideration.
You’ll help build a category-defining legal tech company, transform how hundreds of legal teams operate, and shape the future of the GC role while still doing meaningful, high-impact legal work yourself.

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 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 the General Counsel at Checkbox, you will own and lead the company’s legal work. As our first in-house legal hire, we’re looking for a General Counsel who doesn’t just want to support the business, but help shape it. Someone who loves legal work, but gets itchy feet doing legal work alone. Own the entire legal surface area
Expect primarily commercial legal work, leading high-velocity negotiations across enterprise SaaS MSAs and strategic partnerships
Define and protect our IP strategy, ensuring our product, data, and innovation are defensible
Be the primary legal partner for our people and culture across a globally distributed team
Support data, privacy, and security compliance and risk management while enabling responsible data access and AI adoption at scale
Treat outside counsel as a precision tool, not a default, bringing work in-house wherever possible and holding external advisors to high standards of efficiency, clarity, and impact

Be the voice of the customer internally
Work with Marketing to shape Checkbox’s external narrative by pressure-testing product messaging and positioning through a GC lens
Work with Sales to understand the GC buyer and support revenue enablement to help close more deals
Work with Customer Success to help design strategies to deliver real value to GC customers to drive engagement, retention, and growth
Work with Product to invent what “legal-first product design” looks like by embedding real GC thinking directly into product decisions and design

Be a visible, credible face of Checkbox in the market, representing the company as a modern, thoughtful, and trusted leader in legal technology
Build a point of view on the future of the GC, legal operations, and AI in legal by speaking, writing, and contributing meaningfully to industry conversations
Attend and participate in industry events, panels, and forums while building a personal brand that strengthens Checkbox’s reputation and influence with legal leaders
Join customer and prospect sales conversations to provide a peer-level GC perspective, build trust with legal buyers, and directly support improved deal confidence and win rates

Build a modern legal function from scratch
Design and implement processes, systems, and playbooks before adding headcount
Be an active adopter and evangelist of AI and legal technology, using it to multiply impact rather than defaulting to traditional resourcing models
Establish legal operations as a xrczosw first-class discipline with clear workflows, metrics, and data
Build a modern legal function from a true blank slate, free from legacy systems or outdated ways of working

You have been a General Counsel, Assistant/Associate GC, or Head of Legal at a SaaS company
You genuinely love legal work and being a driver of business outcomes
You deeply value legal operations and process design
You have strong judgment around balancing speed and risk
You enjoy being visible externally through speaking and writing
You already have a strong LinkedIn presence or GC network
11 days paid Federal holidays per year
~ Health insurance, including dental and vision coverage
~401K retirement savings match
~ Fully paid annual trips to company off-sites (past destinations include Australia, Bali, South Korea)