AI Deployment Strategist

About Cooper AI

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 day and unlock meaningful efficiency gains.

Born as a spinout of Nirvana (a $1.5B Series D insurtech company) and backed by Lightspeed, General Catalyst, and Valor, Cooper AI is building from the ground up to modernize a $1T+ global insurance industry. As an AI-powered platform Cooper automates the operational workflows that slow down insurance carriers and brokers, and replace them with real-time AI that helps teams run faster, safer, and smarter.

About the Role

This is a rare opportunity to be one of the first people shaping how Cooper AI reaches the market and delivers value to customers. As an AI Deployment Strategist, you'll run deployments end-to-end: configuring Cooper to each agency's workflows, partnering with engineers on systems integrations, and training users all in service of activating our customers and laying the foundation for lasting adoption. You’ll serve as a trusted advisor to insurance executives while working hand-in-hand with our engineering and product teams. You won't just be deploying software. You'll be helping a critical industry work in a fundamentally different way.

What You'll Do

- Own deployments end-to-end. Run simultaneous customer deployments from kickoff through activation. This includes scoping workflows, configuring Cooper’s skills and automations, setting up integrations with existing systems, and driving adoption across producers, CSRs, and account managers

- Drive activation, not just go-live. Success isn’t handing over a login. It’s the moment an organization changes how they work because Cooper is faster than their old process. You’ll customize the platform, enable champions to be trainers and in-org resources, and obsess over usage until activation is real and sticky.

- Be the trusted advisor in the room. Build real relationships with agency owners and user champions. Translate what AI can do into relevant use cases for agencies that highlight real value. Contribute data-driven insights to roadmap prioritization and adoption initiatives.

What You'll Bring

- 4+ years of experience in management consulting, technical account management, solutions engineering, or enterprise AI/SaaS deployment

- Outcome ownership: Track record of driving complex, multi-stakeholder implementations from kickoff through go-live

- Technical fluency: Comfort scoping integrations and troubleshooting alongside engineers without needing to write code

- Strong communication: Ability to distill a complex AI system into something an agency owner trusts, and a messy customer situation into something engineering can fix in a written, verbal, Zoom, in-person format.

- Bias for action with high EQ: Executes efficiently while bringing stakeholders along. Able to represent the buyer's priorities in a leadership meeting, and debug a workflow with a frustrated CSR in the afternoon

- Problem-solving: Comfort with ambiguity and a default to first-principles thinking

- Analytical instincts: Instinct for measurable business outcomes

Preferred Qualifications

- Degree in Computer Science, Engineering, Mathematics, or a related field; MBA a strong plus

- Experience in commercial insurance, insurtech, or financial services

- Familiarity with enterprise integrations, APIs, or data workflows

- Background in change management and large-scale user adoption

- Prior experience at an early-stage startup where you built processes from the ground up