Account Executive, Mid-Market San Francisco, CA

About Cooper

Cooper is an AI coworker for the insurance industry. Getting a business insured involves mountains of paperwork: filling out repetitive forms, re-typing the same information into one insurance company's website after another, and comparing offers by hand. Cooper does that busywork automatically, right inside the tools people already use, so brokers and their teams can focus on advising clients instead of pushing paper.

We're a small team with deep insurance roots, teaching AI to do real, trusted work in a massive, overlooked industry.

Backed by Lightspeed, General Catalyst, and Valor, Cooper AI is building from the ground up to modernize a $1T+ global insurance industry.

You’ll join a small, high-velocity founding team and work onsite at our San Francisco headquarters. Reporting to the CEO, you’ll own the full sales cycle—from prospecting and discovery through demo, close, and early customer feedback. This is a hands-on role for someone who wants to sell, build, and learn quickly in an environment with high impact and high trust.

Own the end-to-end sales cycle, including outbound prospecting, discovery, product demos, negotiation, and close

Demo Cooper’s software to prospective customers and clearly communicate the value of our AI-driven insurance platform

Close new business and consistently hit or exceed revenue targets

Partner closely with SDRs to strategize prospecting strategy and build pipeline effectively

Partner closely with Product, Engineering, and Leadership to refine messaging, pricing, and positioning

Help build and iterate on our go-to-market strategy as we take new products to market

Capture customer feedback and translate real-world objections into insights that shape product and sales strategy

Represent Cooper with professionalism and curiosity as one of the first faces of our Sales organization

2–5 years of closing experience in a sales role, ideally in software or technology

Demonstrated track record of success against quota or measurable sales goals

Experience running product demos and managing a structured sales process

Strong communication skills and the ability to explain complex ideas clearly

Comfort working in a fast-moving, ambiguous startup environment where you help define the playbook

Experience selling into insurance, logistics, transportation, or adjacent industries

Exposure to early-stage or founding sales roles

Interest in data-driven products, AI, or infrastructure-heavy software

Competitive salary & equity

Monthly wellness stipend

401k with company match

Unlimited PTO

Company sponsored lunch 5x per week

Off sites, happy hours, and team building events