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 radically enhance the lawyer-machine relationship. Our mission is to review complex documents faster and with higher quality than ever before.

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.

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.

Note: 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. Pursuant to New York Labor Law Section 194-b, US Pay Range is $160,000 - $220,000 which represents the base salary we reasonably expect to pay for this position at the time of this posting. Final compensation will be determined based on skills, experience, and qualifications.