Demo

Founding Account Executive at Stealth Legal AI Startup backed by premier VCs

Jack & Jill
Toronto, OH Full Time
POSTED ON 5/29/2026
AVAILABLE BEFORE 6/27/2026
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

Founding Account Executive

Salary

Not Disclosed

Company Description

Stealth Legal AI startup backed by premier venture capital firms

Job Description

As the first dedicated go-to-market hire, you will build the sales function for a stealth startup disrupting the legal industry. You will sell a transformative combination of elite legal expertise and bleeding-edge automation to technology companies and investment firms, defining the sales playbook and pricing strategy from the ground up.

Location

Toronto, Canada / San Francisco, USA

Why this role is remarkable

  • Founding opportunity to shape the commercial strategy of a company reimagining the multi-billion dollar legal profession.
  • Work alongside a high-pedigree team with experience from frontier AI labs, elite law firms, and top-tier North American law schools.
  • High-impact role with clear path to GTM leadership as the company scales and the sales team expands.

What You Will Do

  • Serve as the primary commercial lead and face of the company for prospective clients and General Counsels.
  • Execute the full sales cycle from initial outreach and qualification through to contract execution and onboarding.
  • Partner with the product and legal teams to translate technical capabilities into compelling narratives for legal buyers.

The ideal candidate

  • 3-10 years of experience in B2B sales or business development with a proven track record of closing new business.
  • Previous experience selling professional services or legal technology to sophisticated buyers is highly preferred.
  • Exceptional communication skills and the hustle required to build a go-to-market function from zero in a fast-paced environment.

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.

Salary.com Estimation for Founding Account Executive at Stealth Legal AI Startup backed by premier VCs in Toronto, OH
$116,080 to $180,440
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