C R O S B Y
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.
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.