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

Account Executive, Mid-Market

Salary

$220K - $320K + Equity

Company Description

Cooper is an AI coworker for the $1T+ insurance industry, backed by Lightspeed, General Catalyst, and Valor. By automating mountains of paperwork and manual data entry, Cooper allows brokers to focus on advisory work rather than administrative tasks. The company has already reached significant traction, processing over $180M in premiums.

Job Description

You will join a high-velocity founding team in San Francisco to own the end-to-end sales cycle for Cooper’s AI platform. Reporting directly to the CEO, you’ll drive revenue by prospecting, performing discovery, and closing mid-market deals. You will be a key voice in shaping the GTM playbook and translating customer feedback into actionable product insights.

Location

San Francisco, USA

Why this role is remarkable

• Join a category-defining AI startup at the ground floor, backed by top-tier investors including Lightspeed, General Catalyst, and Valor.
• Work directly with the CEO to build the sales motion from scratch, offering a unique opportunity to shape company strategy.
• Sell a high-traction product into a massive, overlooked market that is already processing over $180M in premiums for early customers.
  
  

What You Will Do

• Manage the full sales cycle from outbound prospecting and discovery to product demonstrations and final contract negotiations with mid-market clients.
• Partner with SDRs and leadership to iterate on messaging, pricing, and positioning as you take new products to the insurance market.
• Capture real-world customer objections and translate them into insights that help the product and engineering teams refine the AI platform.
  
  

The ideal candidate

• Has 2–5 years of closing experience in SaaS or technology sales with a consistent track record of hitting or exceeding revenue targets.
• Demonstrates the ability to run structured sales processes and present technical product demos to non-technical buyers in traditional industries.
• Thrives in fast-paced, onsite startup environments and brings a high level of curiosity regarding AI, data-driven products, and insurance infrastructure.
  
  

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.