Operations

Welcome to Crosby, the next-generation law company!

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 enhance the lawyer-machine relationship radically. We want to review complex documents, for example, 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 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.
  
  

The Role:

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.

What You’ll Do:

• Own mission-critical workflows that blend human and machine to deliver legal work faster and better than ever before
• Design and implement new operational processes, from scoping to rollout, across legal delivery, quality control, training, and client success.
• Partner with product and engineering to prototype and deploy internal tools that increase throughput and reduce error.
• Define and operationalize Crosby’s evolving playbooks, training systems, and incentives as we scale.
  
  

What We’re Looking For:

• 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.
  
  

Why Work at Crosby Legal:

• Competitive salary and equity compensation.
• Comprehensive health, dental, and vision insurance.
• Unlimited PTO
• In-person team in NYC with a collaborative, high-energy environment.
  
  

Apply now to join Crosby and be part of transforming the legal landscape.