Founding Sales / GTM

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.

About the Role:

We’re looking for a Founding Go-To-Market (GTM) Lead 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.

What you’ll do:

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

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

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

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

• Lay the foundation for a future GTM team (sales, marketing, success) by building processes, playbooks, and metrics.

What We’re Looking For:

• 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.

What We Offer

• Direct collaboration with the founders and the opportunity to shape company strategy.

• Autonomy and ownership to build a GTM function from the ground up.

• The chance to have outsized impact at an early-stage company.

Why Work at Crosby:

• Build the Foundation: This is a rare opportunity to build an 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.