Job Description

Job Description

General Counsel

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

The Role

Most GCs say they want to be strategic partners to the business. With this role, it’s unavoidable. 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.

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:

-values

The Position

As the General Counsel at Checkbox, you will own and lead the company’s legal work. But this is not a traditional GC role. This is a builder, operator, and strategic partner role inside a high-growth SaaS company that sells to GCs, meaning your perspective matters everywhere.

You will report directly to the Co-Founder and CEO, be a member of the executive leadership team, and attend Board meetings.

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. Someone who wants to sit at the intersection of law, product, revenue, and technology, and directly influence business outcomes.

What You’ll Do

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
• Lead corporate governance, board processes, and supporting capital raises
• 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 the voice of Checkbox externally

• 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 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

About You

• You have been a General Counsel, Deputy/Associate GC, or Head of Legal
• You genuinely love legal work and being a driver of business outcomes
• You are excited by AI and actively use it in your day-to-day work
• You deeply value legal operations and process design
• You think like a builder and operator, not just an advisor
• You own your lane but contribute broadly across the business
• You bring urgency, pragmatism, and a revenue mindset to decisions
• You have strong judgment around balancing speed and risk
• You enjoy being visible externally through speaking and writing
• You are a strong public speaker and writer
• You are hard-working with a bias for action
• You have a positive outlook, growth mindset, and accountability
• You are coachable, humble, and comfortable with feedback

Nice-to-Have

• You already have a strong LinkedIn presence or GC network
• You’ve founded or worked in an early-stage start-up

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 off-sites (past destinations include Australia, Bali, South Korea)

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