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:

• As the Lead Infrastructure Engineer at Crosby Legal, you will take end-to-end ownership of our cloud systems, developer platform, and security posture as we scale. You’ll work alongside our founding engineering team to build the foundation that powers Crosby’s legal-tech stack.

• This role is perfect for someone who thrives on autonomy, systems thinking, and building reliable, secure infrastructure from the ground up.

What You’ll Do:

• Own and evolve our cloud infrastructure (AWS + Pulumi + GitHub Actions + Modal).

• Build and maintain robust observability, tracing, and alerting systems.

• Lead efforts around security and compliance (IAM, SOC 2 readiness, secure networking).

• Define and enforce best practices for infrastructure reliability and performance.

• Collaborate with software engineers to streamline CI/CD and deploy systems that scale.
  Set the long-term strategy for infrastructure as we grow the product and team.
  

What We’re Looking For:

• 5+ years in DevOps, Site Reliability, or Platform Engineering roles.

• Deep experience with modern cloud infrastructure (preferably AWS) and infrastructure-as-code tools (Pulumi, Terraform, etc.).

• Proficiency with CI/CD pipelines and automation (GitHub Actions or similar).

• Strong experience with observability tooling (e.g., Datadog, OpenTelemetry, Prometheus).

• Understanding of security best practices in cloud environments.

• You’re highly autonomous, thrive in high-ownership settings, and enjoy solving ambiguous problems.

• Passion for building foundational systems in a fast-paced, high-stakes environment.

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.