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.
About the Role
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.
What You’ll Do
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
What You Bring
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
Benefits:
Competitive salary & equity
Medical, dental & vision insurance
Monthly wellness stipend
401k with company match
Unlimited PTO
Company sponsored lunch 5x per week
Off sites, happy hours, and team building events
Skills Required
- 2-5 years of closing experience in a sales role
- Demonstrated success against quota or measurable sales goals
- Experience running product demonstrations
- Experience managing a structured sales process
- Strong communication skills and ability to explain complex ideas clearly
- Comfort working in a fast-moving, ambiguous startup environment
- Experience selling into insurance, logistics, transportation, or adjacent industries
- Experience in software or technology sales
- Exposure to early-stage or founding sales roles
- Interest in data-driven products, AI, or infrastructure-heavy software
What We Do
Cooper builds an AI coworker for commercial insurance teams, automating document-heavy work across the insurance workflow from intake through renewal. It handles repetitive forms, submission processing, quote comparison, proposal drafting, policy checks, certificates, and renewals inside the tools insurance professionals already use. The goal is to reduce administrative busywork for agencies, brokers, insurers, and claims teams so they can spend more time advising clients and doing trusted, relationship-focused work.
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