Senior Enterprise Account Executive, AI Insurance

Cooper; San Francisco (CA); On-site; USD 300,000 - 450,000; Full time

Benefits offered by this job

Competitive salary & equity

Medical, dental & vision insurance

Monthly wellness stipend

401k with company match

Unlimited PTO

Company sponsored lunch 5x per week

Off sites, happy hours, and team build

Job summary

Cooper, headquartered in San Francisco, is hiring for an enterprise software sales role. You will own the full sales cycle, from executive discovery to closing multi-stakeholder deals, targeting high-ACV opportunities within large accounts.

We seek a candidate with 5–10 years closing complex software deals, strong executive presence, and experience navigating procurement and security reviews. Insurance/logistics domains are a plus in this fast-moving startup environment.

Qualifications

• 5–10 years of closing experience in an enterprise software or technology sales role with quota delivery.
• Proven track record of closing complex, high-ACV deals ($100K+ ARR) with multiple stakeholders.
• Experience navigating enterprise procurement, legal review, and security assessments.
• Strong executive presence and ability to build trust with C-suite and VP-level buyers.
• Skilled at consultative discovery, building business cases, and leading tailored demos for technical and non-technical audiences.

Responsibilities

• Own the end-to-end enterprise sales cycle, executive-level discovery, demos, and complex negotiations through procurement.
• Build and manage relationships across multiple stakeholders within large enterprise accounts.
• Demo Cooper's software to senior decision-makers and articulate AI-driven value in business terms.
• Close large, multi-stakeholder deals and consistently hit or exceed revenue targets.
• Develop account plans and coordinate with Product, Engineering, and Leadership to advance opportunities.
• Help define enterprise go-to-market strategy and ideal customer profiles.

Skills

Enterprise software sales

Executive stakeholder management

Complex deal closing

Negotiation

Product demos

Sales strategy

Job description

Cooper, headquartered in San Francisco, is hiring for an enterprise software sales role. You will own the full sales cycle, from executive discovery to closing multi-stakeholder deals, targeting high-ACV opportunities within large accounts.

We seek a candidate with 5–10 years closing complex software deals, strong executive presence, and experience navigating procurement and security reviews. Insurance/logistics domains are a plus in this fast-moving startup environment.