Enterprise Commercial Counsel - AI & Data Licensing

Commercial Counsel

You'll run a large share of Firecrawl's day-to-day commercial contracting. Enterprise deals, data-licensing agreements, vendor paper, partnership terms: you'll draft them, negotiate them, and get them closed. This is not a role where you review other people's paper and send back comments. You'll be across the table from counterparties yourself, sitting next to sales and BD while deals are live, and you'll help build the templates and playbooks that let the company move faster without taking on risk it shouldn't.

You'll work alongside the Senior Commercial & Product Counsel and report to the General Counsel on a legal team that's being built from scratch. The questions here are genuinely novel: who owns AI-generated output, what data access is permissioned and by whom, how liability works for infrastructure that other AI companies build on. Very few lawyers this early in their career get real reps on them.

Salary Range: $246,000–$270,000 USD/year (SF) / $200,000–$211,000 CAD/year (Toronto), plus eligibility for up to $50,000 USD in semi-annual performance bonuses, totaling up to $100,000 USD annually. (Range shown is for US-based employees in San Francisco, CA, and Canada-based employees in Toronto, ON. Compensation is adjusted fairly based on your location's cost of living.)

Equity Range: Competitive equity - details shared during the process.

Location: Location: San Francisco, CA (SF HQ) or Toronto, ON (Toronto Hub). Hybrid, onsite 3+ days a week. Open to remote within US time zones (UTC-5 to UTC-10) for the right candidate.

Job Type: Full-Time

Experience: 3–8 years of commercial, technology, or product counseling experience

Visa: Open to candidates already authorized to work in the US or Canada. In the US, we also support H-1B transfers, F-1 OPT and STEM OPT, TN (Canada and Mexico), and E-3 (Australia). We’re not able to sponsor new H-1B visas for candidates outside the US. For Canada, we’ll consider work permit sponsorship case by case through our Toronto Hub.

About Firecrawl

Firecrawl is the easiest way to turn the web into data AI agents can use. One API call converts any URL into clean, LLM-ready markdown or structured data. It's the boring-hard problem everyone building with LLMs eventually hits, solved.

In September 2026, we raised a $75M Series B led by Smash Capital, and we're spending it building the largest repository of knowledge in the world. We hit 8 figures in ARR in year one and more than doubled it in year two. We have 192k+ GitHub stars, putting us in the top 40 repositories of all time, and developers, agents, and category-defining AI companies build on us every day. Growth like this is rare, and we're just getting started.

We're a small team punching far above our weight. Everyone here owns a real piece of the product and company, end to end, and runs it themselves. No hiding behind process or headcount.

This is a place for people who want to work at the frontier: an AI company building the infrastructure other AI companies run on, not one bolting AI onto an existing product. We move fast, go deep, and are building the tools superintelligence will rely on to gather data from the web. That library is called Alexandria, and it starts now.

What You'll Do

• Draft and negotiate enterprise customer agreements, data-licensing deals, vendor contracts, NDAs, and partnership agreements

• Be the legal partner sales and BD actually want in the room, not the one they route around

• Advise on data rights, privacy, confidentiality, security, IP, indemnification, and limitations of liability

• Work with product and engineering on data access and AI questions as they come up in deals

• Help build and maintain the templates, playbooks, fallback positions, and approval thresholds that keep deals moving without a lawyer in every loop

• Support the compliance programs and company policies the legal team is standing up

• Spot the matters that need the GC, senior counsel, or outside counsel, and escalate them early and cleanly

• Pick up whatever else the company needs legally as we grow, because early legal teams don't get to have narrow scopes

What We're Looking For

• You've negotiated real technology agreements. Not reviewed them. Negotiated them, across the table, with a counterparty's counsel pushing back, and you've held the positions that mattered and conceded the ones that didn't

• You can carry a deal on your own. You don't need someone to structure the negotiation for you or check every redline before it goes out. You take a matter and bring it to signature

• You know exactly when to escalate. This role has real autonomy and that only works if you're good at telling routine from novel, and you flag the novel one early rather than after it's a problem

• You give business advice, not legal cover. Our teams need a recommendation and a risk read they can act on, not a memo listing every possible exposure. If your default answer is no, this will be frustrating for both of us

• You work well with non-lawyers. Most of your internal clients are engineers and salespeople. They'll trust you if you're fast, clear, and unpretentious

• You're an AI super user. Non-negotiable. You should already be using AI heavily in your own practice, and you should want to push it further than anyone has taken it in this profession. We'll give you room to try things that don't have a precedent

• Membership in good standing in at least one US state bar or Canadian provincial law society. Preferred: a J.D. from a T14 law school or comparable academic credentials, and prior experience at an Am Law 100 firm or a comparably sophisticated firm. Exposure to data licensing, privacy, IP, or data-access issues is a plus

What We're NOT Looking For

• A lawyer who runs commercial legal as a gatekeeping function and measures success by deals slowed down

• Someone who needs a fully staffed team, a CLM platform, and defined process before they can be effective

• A pure litigator or generalist looking to pivot into commercial work on the job

• Someone who wants to stay in a specialty lane. This team is four people and the work is whatever comes in

A Note On Pace

We operate at an absurd level of urgency because the window for what we're building won't stay open forever. If that excites you, keep reading. If it doesn't, no hard feelings, but this role probably isn't for you.

If you're a strong lawyer looking for an interesting escape from BigLaw, this is the one. It won't be boring, and you'll build skills at the absolute frontier of AI and the legal profession.

Benefits & Perks

Available to all employees

• Salary that makes sense: $246,000–$270,000 USD/year (SF) / $200,000–$211,000 CAD/year (Toronto), plus eligibility for up to $50,000 USD in semi-annual performance bonuses, totaling up to $100,000 USD annually. Adjusted fairly for location, based on impact, not tenure

• Own a piece: Gain competitive equity in what you're helping build

• Generous PTO: 15 days mandatory, anything after 24 days, just ask (holidays excluded). Take the time you need to recharge

• Parental leave: 12 weeks fully paid, for all parents

• Wellness stipend: $100 USD/month for the gym, therapy, massages, or whatever keeps you human

• Learning & Development: Expense up to $1,000 USD/year toward anything that helps you grow professionally

• Team offsites: A change of scenery, minus the trust falls

• Sabbatical: 3 paid months off after 4 years, do something fun and new

Available to US-based full-time employees

• Full coverage, no red tape: Medical, dental, and vision (100% for employees, 50% for partner and kids). No weird loopholes, just care that works

• Life & Disability insurance: Employer-paid basic life and AD&D, short-term disability, and long-term disability. Coverage for life's curveballs

• Virtual care and a health guide: Teladoc for the couch doctor visit, plus Rightway to answer coverage questions and fight billing errors for you

• Mental health: Talkspace, therapy and psychiatry on your schedule

• Fertility and family building: Carrot, covering you and your partner

• EAP: Free confidential counseling, legal and financial consults, and online will prep through Guardian

• 401(k) plan: Retirement might be a ways off, but future-you will thank you

• Pre-tax benefits: HSA, FSA, and commuter benefits to help your wallet out a bit

• Supplemental options: Extra life and AD&D, accident, critical illness, hospital indemnity, plus pet, legal, and identity protection through MetLife

Available to Canada-based full-time employees

• Full coverage, no red tape: Extended health, dental, and vision through Manulife (Diamond, the top tier), 100% employer-paid for you, your partner, and your kids

• Life & Disability insurance: Employer-paid life, AD&D, short-term disability, and long-term disability. Coverage for life's curveballs

• Virtual care: Dialogue Premium, so you can see a doctor or nurse from your couch, any hour

• Mental health: Talkspace Elite, therapy and psychiatry on your schedule

• Fertility and family building: Carrot, covering you and your partner

• Retirement: Group RRSP through Wealthsimple, so future-you can thank you

Available to SF-based employees

• SF HQ perks: Snacks, drinks, team lunches, intense ping pong, and peak startup energy

• E-Bike transportation: A loaner electric bike to get you around the city, on us

Available to Toronto-based employees

• Toronto Hub perks: Snacks, drinks, team lunches, glass-walled views down University Avenue, and a home base steps from Union Station

• Transit, covered: A PRESTO card loaded for GO Transit, subway, and streetcar, plus station parking if you drive to the train. Winter-proof, on us

Interview Process

Application Review: Send us your resume and a short note on why this excites you. Tell us about a deal you owned, what you fought for, and what you gave up.

Intro Chat (~25 min): A quick conversation to get to know each other before we go deep. What you've been working on, what drew you to Firecrawl, and what you're looking for. Time for your questions too.

Case Chat (~45 min): We'll work through a real problem from our world, a data-licensing structure or an enterprise redline where the standard position doesn't fit, and talk through how you'd approach it. Come ready to think out loud. We care how you reason, not whether you know the market term.

Redline Exercise (Paid, ~90 min): One scoped, realistic document. You mark it up and give us a short read on the two or three issues you'd actually escalate.

Founder Chat (~25 min): Culture, pace, ownership, and how you like to work. Time for your questions too.

Decision: We move fast after the exercise.

If you want real ownership of commercial legal work at the infrastructure layer of AI, before anyone has written the playbook, you should join us.

Apply now.