Forward Deployed Broker

About Cara

Cara is a domain-specific AI platform purpose-built for insurance—a modular system that enables agencies, brokerages, and wholesalers to automate servicing, accelerate sales, and scale operations with a 24/7 digital workforce.

We’re one of the fastest-growing AI companies in the insurance industry, attracting agencies and brokerages of all sizes with an expanding customer base. We’re a team of experts in engineering and insurance from Stripe, Blend, Strategy&, and Travelers, with backing from top-tier VCs, and are scaling our product and team quickly to meet market demand.

About the Role

As a Forward Deployed Broker, you will work directly with our enterprise customers to deploy AI in production and transform their operations with Cara. This is a hybrid role across sales, consulting, and product — you’ll build and scale your own pipeline, embed with customers, redesign workflows to drive adoption, and expand accounts over time.

You will help enterprise brokerages rethink how work gets done with AI. You’ll work closely with operators and executives to identify high-impact opportunities and drive measurable outcomes across the organization.

What You’ll Do

• Embed with enterprise brokerages to understand their workflows across sales, servicing, and operations

• Design and deploy AI workflows using Cara

• Act as a trusted advisor to leadership (COO, Head of Ops, Producers) on how to leverage AI across the organization

• Own the full customer lifecycle from initial deal through onboarding and scaled adoption

• Drive expansion and revenue growth within accounts by identifying high-impact use cases

• Translate real-world workflows into product insights, partnering closely with engineering and product teams

• Prototype quickly, iterate with customers, and deploy solutions in days

• Help define and scale best practices across Cara’s customer base

What You Have

• 3+ years of experience in insurance brokerage (producer, account executive, operations, or consulting)

• Strong relationships or familiarity with mid-market / enterprise brokerages

• You enjoy selling, expanding accounts, and closing deals

• Deep curiosity about AI and how it transforms workflows

• Ability to communicate effectively with both operators and executives

• Builder mindset—you don’t just advise, you implement