About this role
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 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