Account Executive, Enterprise

About Cooper Cooper AI is building AI for commercial insurance, taking the manual, time‑consuming work off professionals' plates so they can focus on what actually matters: serving clients and growing their business. Cooper works directly inside the tools teams already use, turning these workflows into fast, automated experiences that save hours every week and unlock meaningful efficiency gains. 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 enterprise sales cycle—from executive prospecting and multi‑stakeholder discovery through tailored demos, procurement navigation, and close. This is a senior, hands‑on role for someone who thrives in long‑cycle, high‑ACV deals and wants to build the enterprise motion from the ground up. What You’ll Do Own the end‑to‑end enterprise sales cycle, executive‑level discovery, tailored product demos, and complex negotiation through legal and procurement Build and manage relationships across multiple stakeholders—including C‑suite, operations, finance, and IT—within large enterprise accounts Demo Cooper's software to senior decision‑makers and translate the value of our AI‑driven insurance platform into business outcomes that resonate at the executive level Close large, multi‑stakeholder deals and consistently hit or exceed enterprise revenue targets Develop and execute account plans for strategic targets, coordinating resources across Product, Engineering, and Leadership to advance opportunities Help define and build our enterprise go‑to‑market strategy, including ideal customer profiles, sales stages, and commercial frameworks Capture enterprise customer feedback and surface insights that shape product roadmap and positioning for large‑scale deployments What You Bring 5–10 years of closing experience in an enterprise software or technology sales role, with consistent delivery against quota Demonstrated track record of closing complex, high‑ACV deals ($100K+ ARR) involving multiple stakeholders and extended sales cycles Experience navigating enterprise procurement, legal review, and security assessments Strong executive presence and the ability to build trust with C‑suite and VP‑level buyers Skilled at running consultative discovery, building business cases, and leading tailored demos for technical and non‑technical audiences Comfort operating in a fast‑moving, ambiguous startup environment where you help write the playbook—not just follow it Experience selling into insurance, logistics, transportation, or adjacent regulated industries strongly preferred Familiarity with data‑driven products, AI, or infrastructure‑heavy software and the ability to speak credibly about technical value 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 We set our salary ranges using compensation data from companies similar to our stage and size. For this role, the estimated OTE range for this position is $300,000 - $450,000 + accelerators. The actual base salary will vary depending on multiple factors unique to each candidate, including location, job‑related knowledge, transferable skills, work experience and our assessment of your level during the interview process. Cooper offers equity for all full‑time employees, which is not included in the range listed above and will have an impact on your overall compensation. Cooper offers a wide range of best‑in‑class, comprehensive benefits including 100% employer paid healthcare plans, an up to 4% 401k match program, paid time off, parental leave, wellness reimbursement, work‑from‑home stipend and more. Cooper is committed to building a diverse and inclusive workforce. If you’re interested in this role, but do not meet 100% of the qualifications listed above, we encourage you to apply. We’d like to consider you for this position and roles that may be a fit in the future. Cooper is an Equal Opportunity Employer and considers applicants for employment without regard to race, color, religion, sex, orientation, national origin, age, disability, genetics or any other basis forbidden under federal, state, or local law. Cooper considers all qualified applicants in accordance with the San Francisco Fair Chance Ordinance. #J-18808-Ljbffr