Founding IT & Security Operations Lead

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 than ever — 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 both an art and a science — and discovering the frontier between the two is a magnificent puzzle.
Selling work, not software, is the best way to unlock the productivity gains of GenAI in professional services.
In-person collaboration matters. We operate from our NYC office.

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.

What We’re Looking For

Experience

5+ years in IT, Systems, Workplace IT, or Security Operations roles.
Experience supporting fast-growing teams in startup or high-velocity environments.

Ownership & Judgment

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.

Technical Foundation

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.

Customer Mindset

Treats internal users as customers; calm, clear, and empathetic under pressure
Strong written and verbal communicator who sets expectations and follows through

Process Builder

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

Ideal Qualifications

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.

Why Work at Crosby

Competitive salary and meaningful equity.
Comprehensive health, dental, and vision insurance.
Unlimited PTO.
High-ownership role with direct exposure to founders and leadership.
In-person NYC team with a collaborative, fast-moving, and intellectually curious culture.
Opportunity to define how IT and security operate at a company reinventing legal services.

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 $200,000- $250,000 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.