Account Executive

Cara; New York (NY); On-site; USD 90,000 - 130,000; Full time

Job summary

Cara is hiring an Account Executive to drive new business and expand relationships with insurance agencies, brokerages, and MGAs. You’ll own the full sales cycle—from prospecting and discovery through demo, close, and check-ins—while collaborating with our product team to convert prospects into long‑term partners.

This high-impact role places you on the front lines helping agencies adopt domain-specific AI to transform their operations.

Qualifications

• 2+ years closing in B2B SaaS (insurance/fintech/AI beneficial).
• Proven track record of meeting/exceeding quota in high-growth environment.
• Ability to translate complex tech into business value.

Responsibilities

• New Business Development: build pipeline through outbound, inbound, referrals, events.
• Full-Cycle Sales: manage prospecting, qualification, discovery, demos, negotiation, closing.
• Customer Engagement: understand workflows, present tailored solutions with product team.
• Market Expansion: represent Cara at conferences and networking events.

Skills

Closing in SaaS

Quota attainment

Discovery & demos

Communication & relationships

Entrepreneurial mindset

Insurance/Fintech/AI domain knowledge

Job description

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

About the Role

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.

What You’ll Do

• 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.

What You Have

• 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.