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.
Account Executive, Mid-Market at Cooper
Join Cooper, the AI coworker for the $1T+ insurance industry backed by Lightspeed, General Catalyst, and Valor. We are already processing $180M+ in premiums and are looking for a Mid-Market Account Executive to own the full sales cycle at our San Francisco headquarters. Reporting directly to the CEO, you will help build the GTM playbook from scratch and modernize a massive, legacy industry. If you have 2-5 years of closing experience and want to be a founding member of a high-impact sales team, let’s talk.
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Location
San Francisco, United States
Compensation
$220k-$320k + Equity
Company
Cooper
Role overview
Cooper (accessible via the domain askcooper.ai) is an AI coworker for insurance professionals that automates the manual, document-heavy work across the entire insurance workflow, from intake to renewal. It is built for retail agencies, wholesale brokers, managing general agents (MGAs), insurers, and claims third‑party administrators (TPAs). Cooper reads and extracts data from documents, completes insurance applications, navigates carrier portals and claims systems, compares coverage options, and takes actions directly inside the tools that teams already use, reducing the time spent moving information between systems. By handling repetitive paperwork and process tasks, Cooper enables brokers, underwriters, and adjusters to focus on applying judgment, advising clients, building relationships, and growing the business. The company is backed by venture investors including Lightspeed, General Catalyst, and Valor and is headquartered in San Francisco, California.
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.
Who this is a fit for
- 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.
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.
How Jack & Jill work together
I get to know what you’re great at, then find roles you’d never find yourself.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.
I recruit from Jack’s network and make the intro when I spot a great match.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.
Jack gets to know what you're great at and what you want next, then searches 15 million jobs daily and helps you discover roles at companies like this.
Meet Jack
What happens next?
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 your profile’s a match and Cooper wants to meet, Jill will make the intro. In the meantime, Jack will send you excellent alternatives.