About Cooper AI
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.
What you'll do
Own the product roadmap end-to-end — from discovery through launch and iteration — in close partnership with founders and engineering
Get deep into customer workflows: spend time with brokers, carriers, and underwriters to understand the real pain points, not just the surface-level asks
Translate complex, messy insurance processes into clear, buildable product specs that engineers can execute and customers can immediately use
Define and track the metrics that matter — adoption, time saved, retention — and use them to sharpen prioritization decisions
Work directly in the AI product layer: help shape how Cooper's AI agents behave, what they automate, and how they fit into existing tools and workflows, including getting hands-on with building agents and writing code when needed
Build the product culture at Cooper — establish how we talk to customers, how we evaluate ideas, and how we ship with speed and discipline
Partner with sales and customer success to close the loop between what we promise and what we deliver, feeding insights back into the roadmap
What you'll bring
5+ years of product management experience, with a meaningful portion at an early-stage or high-growth company where you shaped the direction — not just executed a plan
A track record of shipping products that changed how people work, ideally in a domain involving complex professional workflows (insurance, fintech, legal, healthcare, or similar)
Strong customer instincts — you can run a discovery call, synthesize 10 conversations into a clear insight, and know the difference between what customers say and what they actually need
Comfort operating in ambiguity: you can define the problem when no one else has, and move forward without a complete picture
Experience working closely with engineers and a genuine appreciation for technical tradeoffs — you can hold your own in architecture conversations without pretending to be an engineer
Excellent written communication — you write specs, briefs, and strategy memos that others want to read, and you can distill complexity into a paragraph
A builder's mentality: low ego, high ownership, obsessed with outcomes over process
Background building AI or automation products, particularly in enterprise or workflow-heavy contexts where the human-AI handoff is nuanced
Preferred qualifications
Experience at a company that went through a 0→1 phase — you've built product infrastructure (processes, templates, rituals) from scratch, not just inherited it
Familiarity with integrations-first products: tools that live inside other tools (CRMs, email clients, agency management systems) rather than replacing them
Quantitative background or strong comfort with data — you can pull your own queries, run cohort analyses, and sanity-check dashboards without relying on a data team
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
Skills Required
- 5+ years of product management experience
- Meaningful experience at an early-stage or high-growth company shaping product direction
- Track record of shipping products that changed how people work
- Experience with complex professional workflows such as insurance, fintech, legal, or healthcare
- Strong customer discovery, synthesis, and product insight skills
- Ability to operate effectively in ambiguity and define problems independently
- Experience partnering closely with engineers and evaluating technical tradeoffs
- Excellent written communication for specifications, briefs, and strategy memos
- Builder mentality with high ownership and outcome focus
- Background building AI or automation products, especially for enterprise or workflow-heavy contexts
- Experience with a 0-to-1 product-building phase
- Familiarity with integrations-first products
- Quantitative background or comfort with queries, cohort analyses, and dashboards
What We Do
Cooper builds an AI coworker for commercial insurance teams, automating document-heavy work across the insurance workflow from intake through renewal. It handles repetitive forms, submission processing, quote comparison, proposal drafting, policy checks, certificates, and renewals inside the tools insurance professionals already use. The goal is to reduce administrative busywork for agencies, brokers, insurers, and claims teams so they can spend more time advising clients and doing trusted, relationship-focused work.
