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ABOUT CROSBY Crosby is built on a simple conviction: a great legal system is the watermark of a great society — and the best legal work comes from combining human expertise with the right technology, not replacing one with the other. Crosby is the first AI-native law firm, helping ambitious companies like Cursor, Ramp, and Cognition sign commercial contracts faster. Legal work is both art and science, and we're mapping the frontier between the two — codifying what can be systematized, amplifying human judgment where it matters most. That's why the right way to bring AI into law isn't to sell software and walk away. It's to own the outcome together: higher-quality work, delivered faster. We build proprietary tools and human-in-the-loop workflows that change what's possible for corporate legal teams. Crosby was founded by Ryan (Stanford Law, Cooley, startup GC) and John (Penn, first 15 engineers at Ramp). Help us transform one of society's most important industries. We believe: - A great legal system is the watermark of a great society. - Legal work is an art and science. We want to discover the frontier between the two and codify the scientific parts, which is a magnificent puzzle. - Selling work, not software, is the best way to realize the productivity gains of GenAI for professional services. The Role: As the second recruiter on our legal team, you’ll run full-cycle hiring across all of our legal roles, from sourcing through close, building scalable processes and helping define what great hiring looks like at Crosby. This is an opportunity to be a strategic partner to leadership, have a meaningful voice in company growth, and leave your mark on the future of our team and culture. The lawyers we hire are energized by the intersection of law and technology, excited to apply AI in their practice, and ready to trade the billable hour for outcomes. They’re in high demand, so winning them is a craft. You’ll evangelize Crosby and learn what each candidate cares about, shaping their experience around it. The people you close are raring to start, and the ones who don’t still leave as fans. What You’ll Do: - Own full-cycle hiring across our legal roles: sourcing, screening, scheduling, and closing. - Partner directly with Henry https://www.linkedin.com/in/henry-klein-412927b4/, hiring managers and leadership to deeply understand each role deeply before you pitch it. - Build scalable processes and track the metrics that tell us what’s working. - Source and engage passive candidates, including lawyers who aren’t looking yet. - Evangelize Crosby and make the case for a different way to practice law. - Close. Move candidates from interested to committed, and turn the ones who pass into referrals and advocates. - Build a candidate experience good enough to become part of how the market sees us. - Hold a high bar as we scale, and protect the team’s time along the way. - Learn from every conversation, and feed it back so we recruit and sell sharper each time. What We’re Looking For: - Recruiting experience in legal specifically, or high-slope recruiting in another domain with the hunger to get up to speed on law fast. - A closer, not just a sourcer. You’ve moved in-demand, discerning candidates over the line. - Strong sourcing instincts and the ability to build pipelines from scratch. - A great communicator who earns trust with candidates and hiring managers alike. - Ability to adapt on the fly in a fast-paced, sometimes ambiguous, start-up environment - Curious about AI and how it's changing professional work, enough to speak to it credibly. - Experience with an ATS (we use Ashby) or the ability to pick it up quickly. Bonus Points: - You’ve been an early or “first” recruiter and love building from 0 → 1 - You’ve recruited lawyers or other high-end professional talent - You are a culture and team builder Benefits: - Competitive salary and equity compensation - Generous, flexible PTO - Medical insurance (multiple plan options through Anthem & Cigna) - HSA or FSA, depending on your plan choice - Dental insurance - Vision insurance - 401(k) match - A collaborative, high-energy environment EQUAL OPPORTUNITY Crosby is an equal opportunity employer. We do not discriminate based upon race, religion, color, national origin, sex (including pregnancy, childbirth, reproductive health decisions, or related medical conditions), sexual orientation, gender identity, gender expression, age, status as a protected veteran, status as an individual with a disability, genetic information, political views or activity, or other applicable legally protected characteristics. Background checks for applicants will be administered in accordance with applicable law, and qualified applicants with arrest or conviction records will be considered for employment consistent with those laws, including the New York City Fair Chance Act. Pursuant to New York Labor Law Section 194-b, the US Pay Range for this position is listed in the job post. Final compensation will be determined based on skills, experience, and qualifications.

Listed by Crosby for a position based in the United States. Employers on this board attest they are hiring domestically.

Writing / Editing

123 days ago

Writer

Crosby · New York City, New York, United States

Pay

$100k–180k

Setting

On-site

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ABOUT CROSBY Crosby is built on a simple conviction: a great legal system is the watermark of a great society — and the best legal work comes from combining human expertise with the right technology, not replacing one with the other. Crosby is the first AI-native law firm, helping ambitious companies like Cursor, Ramp, and Cognition sign commercial contracts faster. Legal work is both art and science, and we're mapping the frontier between the two — codifying what can be systematized, amplifying human judgment where it matters most. That's why the right way to bring AI into law isn't to sell software and walk away. It's to own the outcome together: higher-quality work, delivered faster. We build proprietary tools and human-in-the-loop workflows that change what's possible for corporate legal teams. Crosby was founded by Ryan (Stanford Law, Cooley, startup GC) and John (Penn, first 15 engineers at Ramp). Help us transform one of society's most important industries. ABOUT THE ROLE In today’s ever-evolving digital landscape, we are truly living in a remarkable golden age of content. It’s not just that it’s easier to write pieces, but also the finished product is more enjoyable to read. Wait, sorry, you’re absolutely right–that was AI slop! Take 2: we’re hiring a human writer. LLMs can produce a lot of average writing. We sell to a lot of not-average people. Founders of fast-scaling AI startups. General counsels at Fortune 500 companies. Chief Revenue Officers at trusted financial services firms. We’re hiring a 99th percentile writer who can reach our 99th percentile customers. WHAT YOU’LL DO 1. Write short and long form essays, blog posts, and social posts for various ICPs we care about (executives, legal leadership, sales leadership, and engineers and researchers) 2. Help founders, execs, and engineers get their thoughts organized clearly and polished for their audiences 3. Produce other content: build story boards for videos we’ll shoot, write copy for new website landing pages, cut the best clips from an interview to post on social 4. Wear many hats: some days we’re crafting the right pitch for our founder to go on a podcast, others we’re racing around the east village finding a screen printer who will make last minute swag for an event tonight WHO YOU ARE 1. Experience: 2+ years of experience 2. Track record of excellent written work 3. Ownership: Driven to take responsibility for projects from ideation through execution 4. Curious, eager learner able to quickly pick up new topics 5. Have good intuition on when to push hard to edit something to the best copy vs let the author’s voice shine through 6. Able to explain complex topics succinctly 7. Fast mover: you know that if the right idea hits at the right moment we need to write great copy in minutes to get it on the timeline 8. Strong understanding of technical topics and ability to write crisp engineering blog posts is a plus 9. Proficient in video editing is a plus EQUAL OPPORTUNITY Crosby is an equal opportunity employer. We do not discriminate based upon race, religion, color, national origin, sex (including pregnancy, childbirth, reproductive health decisions, or related medical conditions), sexual orientation, gender identity, gender expression, age, status as a protected veteran, status as an individual with a disability, genetic information, political views or activity, or other applicable legally protected characteristics. Background checks for applicants will be administered in accordance with applicable law, and qualified applicants with arrest or conviction records will be considered for employment consistent with those laws, including the New York City Fair Chance Act. Pursuant to New York Labor Law Section 194-b, the US Pay Range for this position is listed in the job post. Final compensation will be determined based on skills, experience, and qualifications.

Listed by Crosby for a position based in the United States. Employers on this board attest they are hiring domestically.

AI/ML

207 days ago

Head of Data

Crosby · New York City, New York, United States

Pay

$220k–375k

Setting

On-site

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ABOUT CROSBY Crosby is built on a simple conviction: a great legal system is the watermark of a great society — and the best legal work comes from combining human expertise with the right technology, not replacing one with the other. Crosby is the first AI-native law firm, helping ambitious companies like Cursor, Ramp, and Cognition sign commercial contracts faster. Legal work is both art and science, and we're mapping the frontier between the two — codifying what can be systematized, amplifying human judgment where it matters most. That's why the right way to bring AI into law isn't to sell software and walk away. It's to own the outcome together: higher-quality work, delivered faster. We build proprietary tools and human-in-the-loop workflows that change what's possible for corporate legal teams. Crosby was founded by Ryan (Stanford Law, Cooley, startup GC) and John (Penn, first 15 engineers at Ramp). Help us transform one of society's most important industries. ABOUT THE ROLE As Head of Data at Crosby, you'll play a critical role in defining and leading our data strategy across the company. You’ll be responsible for building the systems, pipelines, and teams that power our AI models, product analytics, and decision-making infrastructure. You’ll work closely with engineering, product, and legal teams to ensure we are leveraging data as a core competitive advantage — from improving model performance to driving business insights. This is a highly strategic and hands-on role, requiring both technical depth and strong leadership. WHAT YOU'LL DO 1. Own data strategy: Define and execute Crosby’s data strategy across ML, analytics, and infrastructure. 2. Build and scale data systems: Design and implement robust data pipelines, storage systems, and tooling to support both product and modeling needs. 3. Enable AI performance: Partner closely with ML and engineering teams to improve data quality, labeling systems, and feedback loops that drive model performance. 4. Drive analytics and insights: Establish metrics, dashboards, and analytical frameworks to support product, business, and operational decision-making. 5. Lead and grow the team: Hire, mentor, and manage a high-performing data team across data science, analytics, and data engineering. 6. Ensure data quality and governance: Build systems and processes to ensure data accuracy, consistency, and reliability across the organization. WHO YOU ARE 1. 8+ years of experience in data science, data engineering, or analytics, with experience leading or managing teams 2. Strong technical foundation in data systems, including experience with data pipelines, warehousing, and large-scale data processing 3. Experience working closely with machine learning teams and understanding the data needs of ML systems 4. Proven ability to define metrics, build analytical frameworks, and drive data-informed decision-making 5. Strong leadership skills with experience building and scaling teams in fast-paced environments 6. Excellent communicator who can work effectively across technical and non-technical stakeholders 7. Highly organized, pragmatic, and motivated to build systems that drive real-world impact EQUAL OPPORTUNITY Crosby is an equal opportunity employer. We do not discriminate based upon race, religion, color, national origin, sex (including pregnancy, childbirth, reproductive health decisions, or related medical conditions), sexual orientation, gender identity, gender expression, age, status as a protected veteran, status as an individual with a disability, genetic information, political views or activity, or other applicable legally protected characteristics. Background checks for applicants will be administered in accordance with applicable law, and qualified applicants with arrest or conviction records will be considered for employment consistent with those laws, including the New York City Fair Chance Act. Pursuant to New York Labor Law Section 194-b, the US Pay Range for this position is listed in the job post. Final compensation will be determined based on skills, experience, and qualifications.

Listed by Crosby for a position based in the United States. Employers on this board attest they are hiring domestically.

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