Strategic Finance Lead

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 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.

This is Crosby’s first dedicated finance hire. We expect this role to be a senior individual contributor with broad ownership and high visibility.

As Strategic Finance Lead, you’ll have the unique opportunity to build the financial foundation that helps Crosby scale. You’ll own the core models, planning processes, and reporting systems that shape how we make decisions across the business.

In this role, you’ll work directly with the founders and partner closely with leaders across growth, legal, operations, and engineering. You’ll help Crosby understand what is happening in the business, what should happen next, and where we should invest.

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  Own Crosby’s financial model across revenue, margin, headcount, cash, and scenario planning.

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  Run the company’s forecasting and planning cadence, including bi-weekly reviews, quarterly planning, and board support.

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  Build the financial frameworks behind how Crosby scales, including pricing, capacity planning, utilization, and unit economics.

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  Work closely with growth on pipeline, forecasting, pilots, expansion, and go-to-market efficiency.

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  Own cash planning, runway analysis, and capital allocation work.

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  Partner with external accounting, tax, and audit firms to keep the financial foundation clean and reliable.

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  Support fundraising, investor reporting, and other high-priority strategic projects as needed.

• Experience: 5+ years in strategic finance, FP&A, investment banking, private equity

• Problem-focused: Strong sense of the problem behind a problem and good judgment about what matters most

• Builder mindset: Excited about the opportunity to establish systems, models, and operating rhythms from the ground up

• Collaborative: Effective communicator who thrives in cross-functional teams and can work closely with both technical and non-technical leaders

• Ownership: Driven to take responsibility for projects from ideation through execution

• Hands-on: Excited to own the work directly

• Curiosity: Motivated by understanding how a business really works and using that understanding to improve decisions

• Strong financial modeling and analytical judgment

• Experience in SaaS, tech-enabled services, marketplaces, or other operationally complex businesses

• Experience working with leadership teams on forecasting, planning, and KPI development

• Experience with SQL, BI tools, or data analysis workflows

• Experience with legal services or hybrid software plus services businesses is a plus.