Founding Account Executive

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).

• 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.

We’re looking for a Founding Account Executive to build and own the commercial side of our business. As one of the first hires, you’ll partner closely with the founders to define our positioning, acquire early customers, and lay the foundation for scalable growth.

This role is ideal for a builder who thrives in ambiguity, can wear multiple hats, and is excited to create a playbook for sales and growth.

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  Build and execute the end-to-end sales motion: sourcing leads, running discovery, managing demos, negotiating contracts, and closing deals.

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  Develop our early marketing strategy: content, campaigns, events, and thought leadership.

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  Establish and manage our customer success approach to ensure adoption, retention, and advocacy.

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  Collect feedback from customers and the market to influence product roadmap and strategy.

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  Lay the foundation for a future sales teams by building processes, playbooks, and metrics.

• 3–8+ years in sales, business development or growth roles at high-growth startups (bonus if you’ve been an early hire).

• Track record of closing enterprise or mid-market deals and building pipeline from scratch.

• Strong understanding of B2B SaaS go-to-market motions (sales-led, PLG, partnerships).

• Data-driven, but willing to experiment and move fast.

• Excited about being a founding team member, with the associated risk/reward, ownership, and impact.

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 $150,000 - $375,000 base plus variable 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.