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). We work together, in person, in New York City — because the best ideas still happen in the same room. Help us transform one of society's most important industries.

About the role

As Crosby’s first dedicated IT & Security Operations Lead, you’ll own the systems, processes, and day-to-day operations that keep our team productive, secure, and unblocked.

This is a hands-on, high-ownership role at a fast-growing Series B company. You’ll design and run Crosby’s IT function end-to-end — from onboarding new hires and managing hardware, to securing devices and identities, to building repeatable processes that scale with the company.

You’ll work closely with the founders, engineering, People Ops, and Finance to define how IT operates at Crosby. Your work will directly impact employee experience, security posture, and the company’s ability to scale efficiently.

What you’ll do

• Own employee IT from end to end: onboarding, offboarding, access management, and day-to-day support.

• Design and operate our endpoint management strategy (laptops, security baselines, patching, encryption).

• Manage identity and access systems (SSO, MFA, role-based access, admin separation).

• Build and run a lightweight helpdesk system with clear intake, prioritization, and SLAs.

• Procure, deploy, and manage hardware inventory and lifecycle (ordering, spares, repairs, replacements).

• Support in-person office IT needs (Wi-Fi, conference rooms, AV, printers as needed).

• Handle security operations basics: phishing response, lost devices, access incidents, vendor security reviews.

• Establish clear documentation, runbooks, and self-service resources to reduce ad-hoc requests.

• Partner with People Ops and Finance on tooling, procurement, and compliance initiatives (e.g., SOC 2).

• Evaluate and manage vendors, MSPs, and external tools as needed.
  

Who you are

• 5+ years in IT, Systems, Workplace IT, or Security Operations roles.

• Experience supporting fast-growing teams in startup or high-velocity environment

• Comfortable being the first IT hire and building systems from scratch.

• Strong security instincts (least privilege, MFA everywhere, no risky shortcuts).

• Able to balance speed, usability, and risk in a pragmatic way.

• Hands-on experience with identity systems (Google Workspace or M365, Okta/Entra).

• Experience with endpoint management (Jamf, Intune, Kandji, or similar).

• Familiarity with EDR/AV, device encryption, patch management, and SaaS administration.

• Treats internal users as customers; calm, clear, and empathetic under pressure

• Strong written and verbal communicator who sets expectations and follows through

• Enjoys turning chaos into clean workflows, documentation, and automation.

• Experience supporting in-person or hybrid offices.

• Basic scripting or automation experience (Bash, PowerShell, Python).

• Prior involvement in SOC 2 / ISO 27001 or similar compliance efforts.

• Experience working with MSPs or outsourced IT vendors.

Benefits & Perks

• Unlimited PTO

• Lunch & dinner in the office every day

• Medical insurance (multiple plan options through Anthem & Cigna)

• HSA or FSA, depending on your plan choice

• Dental insurance

• Vision insurance

• One Medical membership

• 401(k) match

• In-office desk setup stipend
  

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.