GTM - AI Native Sales ($200K - $250K + Equity) at WorkOS, Inc.

This is a job that Jill, our AI Recruiter, is recruiting for on behalf of one of our customers. She will pick the best candidates from Jack’s network.

The next step is to speak to Jack.

Job Title GTM - AI Native Sales

Salary $200K - $250K + Equity

Company Description WorkOS, Inc. is a $2B developer tools platform that recently raised a $100M Series C led by Meritech and Sapphire. We provide the critical infrastructure—like authentication and identity—that powers the world’s most successful AI companies, including OpenAI, Perplexity, and Cursor, helping them become enterprise-ready instantly.

Job Description As a GTM lead for AI Native Sales, you will drive the next chapter of WorkOS, Inc.’s developer-first sales motion. You’ll own the end-to-end revenue cycle, selling complex technical infrastructure to product-minded engineers and CTOs. By leveraging AI-native workflows, you’ll experiment with innovative pipeline-building strategies to scale our impact across the enterprise landscape.

Location San Francisco and New York City, USA

Why this role is remarkable

• Join a $2B unicorn at the frontier of AI infrastructure, powering the authentication and identity layers for industry leaders like OpenAI, Perplexity, and Vercel.
• Work in a high-agency environment backed by $100M in Series C funding from premier investors including Meritech, Sapphire, Greenoaks, and Craft Ventures.
• Shape the future of Human and Agent Authentication, solving the critical “who are your agents?” challenge for the next generation of software companies.

What You Will Do

• Own the entire sales cycle from outbound prospecting and technical discovery to closing and expansion for high-growth AI and software companies.
• Partner with Solutions Engineers to deliver consultative, developer-first buying experiences that simplify complex enterprise requirements like SSO, Directory Sync, and RBAC.
• Run high-velocity experiments using modern AI and automation tools to optimize top-of-funnel conversion, messaging, and pipeline generation strategies.

The ideal candidate

• Possesses significant experience in technical SaaS sales or a quota-carrying role, with a proven ability to communicate effectively with engineers and CTOs.
• Demonstrates high agency and a competitive spirit, thriving in ambiguous early-stage environments where they must create momentum rather than waiting for it.
• Shows proficiency in using modern AI-native tools and workflow builders to enhance sales output quality and maintain a rigorous, data-driven pipeline.

Who are Jack & Jill? Ok, I’ll go first. I’m Jack, an AI that gets to know you on a quick call, learning what you’re great at and what you want from your career. Then I help you land your dream job by finding unmissable opportunities as they come up, supporting you with applications, interview prep, and moral support.

And I’m Jill, an AI Recruiter who talks to companies to understand who they’re looking to hire. Then I recruit from Jack’s network, making an introduction when I spot an excellent candidate.

How does this work?

• Jack’s an AI agent for job searching and career coaching. He works for you.
• Jill is the AI recruiter working for the company. She recruits from Jack’s network.
• If it’s a match and the company wants to meet you, they’ll make the intro. In the meantime, if you’d like, Jack will send you excellent alternatives.

We never post fake jobs This isn’t a trick. This is an open role that Jill is currently recruiting for from Jack’s network.

Sometimes Jill’s clients ask her to anonymize their jobs when she advertises them, which means she can’t share all the details in the job description.

We appreciate this can make them look a bit suspect, but there isn’t much we can do about it.

Give Jack a spin! You could land this role. If not, most people find him incredibly helpful with their job search, and we’re giving his services away for free.