Engineering Manager

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 our Engineering Manager, you will be a foundational leader responsible for scaling our people, processes, and technology. Reporting directly to the CTO, you will take full ownership of the engineering team, enabling them to do the best work of their careers while ensuring we execute effectively on our ambitious product vision.

Your primary mission is to build the machine that builds the machine. This is a role for a leader who thrives on building teams, defining technical strategy, and creating an environment where engineers can ship high-quality products at pace

What You’ll Do:

• Lead & Mentor: Manage, coach, and grow a high-performing engineering team (comprising junior, senior, and staff+ engineers). Own all aspects of people management, including 1:1s, performance reviews, and career development, with a focus on turning our junior talent into senior leaders

• Define Technical Strategy: Drive the long-term technical vision for Crosby’s platform. You will own the core architectural decisions, ensuring our systems are scalable, reliable, and prepared for future complexity

• Scale the Team: Partner with our recruiter to own the end-to-end hiring process for the engineering team. You will define roles, interview, and close top-tier senior product and machine learning engineers to meet our growth targets

• Drive Execution: Refine and scale our engineering processes to improve velocity and execution quality. While you won't be responsible for maintaining the product roadmap, you will be the key partner for product and the founders in translating company goals into a well-executed technical reality

• Collaborate & Influence: Work closely with cross-functional counterparts to ensure the engineering team is aligned with business objectives and delivering maximum impact for our users and legal experts.

What We’re Looking For:

• Experience: 7+ years of software engineering experience, with at least 3+ years in a direct engineering management role

• Proven Team Builder: You have a demonstrated track record of successfully hiring and scaling engineering teams, ideally through a similar growth phase (ex: from 10 to 50+)

• Strong Technical Acumen: You are a strong technical generalist with deep knowledge of system design and architecture. While you won't be expected to code day-to-day or be an expert in our specific stack, you have the credibility to lead senior engineers and make critical architectural decisions

• People-First Leader: You are passionate about developing engineers and building a supportive, high-trust culture. You lead with empathy and have a strong playbook for mentorship and career growth

• Builder Mindset: You are excited by the opportunity to build process and structure in a fast-growing startup environment. You know when to introduce process and when to stay nimble

• Ownership: You are a pragmatic leader who takes full responsibility for the team's success, from shipping features to hitting hiring goals

Ideal Qualifications:

• Experience in a high-growth, venture-backed startup environment (Series A/B)

• Familiarity with our technical domain (AI, LLMs, NLP) is a strong plus, but not a requirement

Why Work at Crosby:

• Build the Foundation: This is a rare opportunity to build an engineering organization from the ground up. You will shape the team, its culture, and its processes for years to come

• Massive Impact: Play a pivotal leadership role in transforming a massive, antiquated industry with technology

• Complex Challenges: Solve fascinating technical problems at the intersection of AI, NLP, and legal services

• Competitive salary and significant equity compensation

• Comprehensive health, dental, and vision insurance

• 401k (including employer match on contributions made while employed by Crosby)

• Flexible PTO

• In-person team in NYC with a collaborative, high-energy environment

Apply now to join Crosby and build the future of 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 - $260,000 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.