Operations Lead

We're a team of technologists and legal experts collaborating closely to reimagine corporate legal services from the ground up. We build proprietary technology and human in the loop workflows to radically enhance the lawyer machine relationship. Our mission is to review complex documents faster than ever and with perfect quality

Crosby was founded by Ryan (Penn, Stanford Law, ex Cooley, former GC) and John (Penn M&T, ex Ramp, ex Google)

We believe:

• A great legal system is the watermark of a great society.

• Legal work is art and science. We are discovering the frontier between the two— codifying what can be systematized, and amplifying human expertise where judgment matters most.

• The right way to deploy AI in law isn’t by selling software. It’s by selling outcomes — higher-quality legal work, delivered faster and more efficiently

• In an in-person culture at our NYC office.

• 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.

• In an in-person culture at our NYC office.

This is not your typical bizops role. Operations are core to our business and are a competitive advantage, so we are designing an ambitious, world class org.

As a member of the Operations Team at Crosby, you will take full ownership of scaling the best law firm ever built – designing and optimizing complex human-in-the-loop workflows, cracking our automation, and ensuring quality.

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  Own mission-critical workflows that blend human and machine to deliver legal work faster and better than ever before

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  Design and implement new operational processes, from scoping to rollout, across legal delivery, quality control, training, and client success.

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  Partner with product and engineering to prototype and deploy internal tools that increase throughput and reduce error.

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  Define and operationalize Crosby’s evolving playbooks, training systems, and incentives as we scale.

• 2–5 years of experience in operations, consulting, finance, or a similarly analytical and high pressure, execution-focused environment. Priority given to former founders.

• Deep curiosity about how things work—and how they can work better.

• Proven ability to own complex systems or projects end-to-end, especially in ambiguous or high-stakes settings.

• Excitement about working in-person with a team that values precision, pace, and constant reinvention.

• An interest in law or legal services is a plus, but not required—this is an operations-first role.