GC AI is the fastest-growing and most trusted legal AI platform for in-house legal teams. We're building the future of legal work, and we're doing it fast. You'll join at a pivotal moment—when decisions matter, impact is immediate, and the runway to shape your career is wide open. We’re a high-performing team where you'll have real ownership and influence from day one.

More than 1,700 companies use GC AI to drive their business forward, including 150+ public companies, 25+ unicorns, and brands such as News Corp, Miro, Bass Pro Shops, Snyk, Skims, Liquid Death, Vercel, Zscaler, and TIME.

We've 10x'd revenue in 12 months, raised a $60 million Series B ($555 million valuation), and are growing faster than ever. We are backed by incredible investors, including Scale Venture Partners, Northzone, Sound Ventures, and Guillermo Rauch, CEO of Vercel.

If you thrive when the stakes are high and the path isn't paved, you'll love it here. Our six guiding principles are: 1% better every day, customer obsession, ship today, find a way, care deeply, and own it completely. Come shape the future of legal work with us.

About The Role

As Associate General Counsel, Commercial, you'll lead and scale GC AI's commercial legal function, reporting directly to the General Counsel. You'll own the full commercial deal cycle for a company growing at extraordinary speed, supporting enterprise and mid-market transactions globally while building the infrastructure, playbooks, and team that will carry us through the next phase of growth.

This role sits at the intersection of legal, sales, product, and customer success, and the right person will be as comfortable closing a complex enterprise deal on customer paper as they are designing scalable self-serve resources for go-to-market teams. This is a sell-side role: you will be representing GC AI as the vendor selling its product, not buying or procuring it. At a company that builds legal AI, you'll also have a front-row seat to the future of how commercial legal work gets done.

The Impact You Will Have

Own and drive the commercial legal function, directly enabling GC AI's revenue growth and customer expansion.
Continue building our commercial legal infrastructure (playbooks, escalation frameworks, template libraries, and self-serve resources) that scales with the business.
Serve as a trusted advisor to senior leadership, distilling complex deal risks into clear, actionable guidance.
Lead, mentor, and develop the commercial legal team.
Push GC AI's product to its limits in real commercial workflows, becoming a primary driver of how it evolves for the commercial use case.
Partner closely with the product team as the voice of commercial legal, turning your day-to-day deal work into structured feedback that shapes the roadmap.

What You'll Do

Independently manage the full commercial deal cycle from negotiation through close, including complex enterprise transactions and customer paper.
Draft, review, and negotiate the full range of commercial agreements (MSAs, order forms, DPAs, NDAs, and bespoke terms) from the sell side.
Build and iterate on commercial playbooks, escalation frameworks, and template libraries.
Create self-serve resources that empower sales, customer success, and other go-to-market teams to move faster.
Partner cross-functionally with sales, product, customer success, and security teams to balance legal risk with deal velocity.
Advise senior leadership on commercial deal strategy, risk allocation, and market-facing legal issues.
Own quarter-end and month-end closing cycles, doing whatever it takes to get deals across the line on the timelines our customers and sales team require, including during evenings and weekends.
Manage, mentor, and develop members of the commercial legal team.
Use GC AI as your primary tool across the full commercial deal cycle and stress-test it against real enterprise transactions, surfacing gaps, edge cases, and opportunities before our customers hit them.
Work hand-in-hand with product and engineering, providing detailed, prioritized feedback grounded in commercial legal practice to make the product the strongest in the market for sell-side commercial teams.
Translate commercial legal workflows into product requirements and self-serve resources, helping define what "great" looks like for the commercial use case both internally and for our customers.
Act as a design partner and early adopter for new features, validating them in live deals and championing the ones that move the needle.
Take on additional projects and tasks as needed in response to the evolving needs of a fast-growing startup.

Required Experience

JD and active bar membership in at least one US jurisdiction.
12–15 years of technology transactions experience, with a substantial portion supporting a B2B SaaS environment.
Currently sitting in an in-house, sell-side commercial legal role at a B2B SaaS company. You must be representing the vendor selling the product. Candidates whose current focus is procurement, vendor management, or buy-side contracting are not a fit for this role.
Currently managing a team of at least two legal professionals (direct reports).
Primary focus on commercial transactions across the Americas.
Demonstrated ability to independently manage a full commercial deal cycle from negotiation through close, including complex enterprise transactions and customer paper.
Experience building or scaling commercial legal infrastructure: playbooks, escalation frameworks, template libraries, and self-serve resources for go-to-market teams.
Strong executive-facing communication skills, with the ability to distill complex legal and business issues into clear, actionable guidance for senior leadership.
Proven ability to balance legal risk with business objectives while maintaining deal velocity.
Experience partnering cross-functionally with sales, product, customer success, and security teams.
Comfort working under pressure, particularly during month-end and quarter-end closing periods.

Nice To Have

Experience managing commercial legal matters across global markets in addition to the Americas.
Experience at a high-growth startup or scale-up company (Series B through pre-IPO).
Familiarity with AI, machine learning, or legal technology sectors.
Privacy certification (CIPP/US, CIPP/E) or substantive privacy experience, including advising on GDPR, CCPA, and state privacy laws.
Experience advising on product and AI-related legal issues, including data processing, model training, and responsible AI frameworks.
Experience implementing or managing AI-powered legal workflows.
Prior big law firm experience in technology transactions.
You are already a GC AI user.
Prior experience as a design partner, beta tester, or product advisor for a legal tech or SaaS product, ideally informing a commercial or contracting workflow.

A Note On Pace

We’re building something new in a once-in-a-generation shift in technology and the legal industry, so we move at a relentless pace. We expect urgency, ownership, and good judgment even when things aren’t perfectly clear. If you need structure and consensus to do your best work, this isn’t the right place for you. If you thrive in ambiguity and growth, work with intensity, and want real responsibility, keep reading. We’re excited to meet you.

Location

We have a preference for candidates in the following locations: San Mateo, CA; Chicago, IL; NYC, NY; Provo, Utah; Seattle, Washington. This role is for U.S.-based candidates only.

Location Policy

This is a remote role unless you fall within the following parameters. If you live within approximately 50 miles of our San Mateo, CA or Provo, UT office, the position follows a hybrid schedule with in-office days on Tuesdays, Wednesdays, and Thursdays.

Equal Opportunity Employment

GC AI is an equal opportunity employer that supports workplace diversity and does not discriminate on the basis of race, color, religion, gender identity/expression, national origin, age, military service eligibility, veteran status, sexual orientation, marital status, physical or mental disability, or any other protected class. GC AI is committed to working with and providing reasonable accommodation to applicants with physical and mental disabilities. #LI-GCAI

Fraud Notice to GC AI Applicants

To protect yourself against phishing and recruitment fraud, please note that GC AI only accepts job applications through our official careers page at https://gc.ai/careers and through sponsored jobs on LinkedIn. All legitimate communication from our team regarding job opportunities will come from a GC AI team member with a @gc.ai or @getgc.ai email address.

GC AI will never:

Refer you to external websites to apply
Conduct interviews over email, chat platforms, or messaging apps
Ask you to provide payment or purchase equipment
Request personal or financial information such as your mailing address, social security number, credit card numbers, or banking information during the application process

Examples of fraudulent email addresses:

info.gcai.careers.com@gmail.com
info.gc.aicareers.online.com@gmail.com
Any email address ending in @gmail.com, @yahoo.com, or other free email services

If you are contacted by someone claiming to be from GC AI via an unofficial channel or from a suspicious email address, please do not share any information. Mark the communication as "phishing" or "spam" and do not respond.