Account Executive

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, backed by top-tier VCs, and are scaling our product and team quickly to meet market demand.

As an Account Executive at Cara, you’ll be responsible for driving new business and expanding relationships with insurance agencies, brokerages, and MGAs. You’ll manage the full sales cycle—from prospecting and discovery through demo, close, and check-ins—while working closely with our product team to ensure prospects become long-term partners.

This is a high-impact role where you’ll be on the front lines helping agencies and brokerages adopt domain-specific AI to transform how they operate. You’ll collaborate directly with the founders, shape the go-to-market motion, and play a critical role in Cara’s growth story.

• New Business Development: Build and manage a strong pipeline of agency and brokerage prospects through outbound outreach, inbound leads, referrals, and industry events.

• Full-Cycle Sales: Own the sales process end-to-end—prospecting, qualification, discovery, product demos, negotiation, closing, retention, and expansion.

• Customer Engagement: Work closely with prospects to understand their workflows and demonstrate Cara’s value; work with the product team to present tailored solutions that fit their needs.

• Market Expansion: Represent Cara at conferences and networking events, positioning the company as the leading AI partner for insurance.

• 2+ years of closing experience in B2B SaaS sales, ideally with exposure to insurance, fintech, or AI/automation markets.

• Proven track record of meeting or exceeding quota in a high-growth environment.

• Strong discovery, demo, and closing skills, with the ability to simplify complex technology into clear business value.

• Excellent communication and relationship-building abilities with both executive decision-makers and frontline staff.

• Highly motivated, entrepreneurial mindset—thrives in a fast-paced, ambiguous environment with significant ownership.

• Bonus: Experience selling to insurance agencies, brokerages, or financial services organizations.