AI-Driven Insurance Sales Executive

Cooper AI; San Francisco (CA); On-site; USD 140,000 - 210,000; Full time

Benefits offered by this job

Competitive salary

Equity

Medical, dental & vision insurance

Monthly wellness stipend

401k with company match

Unlimited PTO

Company lunch 5x per week

Off-sites and team events

Job summary

Cooper AI in San Francisco is seeking an accomplished sales professional to join our founding team. You’ll own the full sales cycle—from outbound prospecting and discovery through demo, negotiation, and close—while helping shape our go-to-market approach.

You’ll partner with Product, Engineering, and Leadership to refine messaging and pricing, demo our AI-driven insurance platform, and drive rapid revenue growth in a fast-moving startup environment.

Qualifications

• 2–5 years of closing experience in a sales role.
• Proven track record of meeting or exceeding quota.
• Experience running product demos and managing a structured sales process.
• Strong communication skills and ability to convey complex ideas.
• Comfort in a fast-moving 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.

Responsibilities

• 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 platform.
• Close new business and consistently hit or exceed revenue targets.
• Partner with SDRs to strategize prospecting and build pipeline.
• Collaborate with Product, Engineering, and Leadership to refine messaging, pricing, and positioning.
• Help build and iterate our go-to-market strategy as we launch new products.
• Capture customer feedback and translate objections into product/sales insights.
• Represent Cooper professionally as a key face of the Sales organization.

Skills

Closing experience

Communication skills

Product demos

Sales process discipline

Startup environment adaptability

Insurance industry knowledge

Early-stage sales exposure

Interest in AI/data-driven products

Job description

Cooper AI in San Francisco is seeking an accomplished sales professional to join our founding team. You’ll own the full sales cycle—from outbound prospecting and discovery through demo, negotiation, and close—while helping shape our go-to-market approach.

You’ll partner with Product, Engineering, and Leadership to refine messaging and pricing, demo our AI-driven insurance platform, and drive rapid revenue growth in a fast-moving startup environment.