Account Executive, Mid-Market
Most applications go out cold — see where you stand first. No sign-up to start.
Don't just apply. Show up ready.
Olive works from this exact posting — no sign-up to start.
At a glance
Job overview
Cooper is hiring an Account Executive, Mid-Market. Cooper is an AI‑driven coworker for the insurance industry, helping brokers automate paperwork. The company seeks an Account Executive to own the full sales cycle, conduct demos, close deals, and shape go‑to‑market strategy while collaborating with product, engineering, and leadership on a fast‑moving startup team in San Francisco.
Key focus areas include Own end‑to‑end sales cycle including prospecting, discovery, demos, negotiation, and close, Demo Cooper’s software to prospective customers and communicate platform value, and Close new business and consistently meet or exceed revenue targets.
Important skills include Sales, Product Demonstration, Negotiation, User Feedback, Go-to-Market Strategy, and Outbound Prospecting.
Skills & qualifications
Skills
Qualifications
Benefits
Full job description
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
You've read the whole posting — now see how you match it.