Sales Development Representative

About Cara

Cara is a domain-specific AI platform purpose-built for insurance—a modular system that enables agencies, brokerages, and MGAs 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 a Sales Development Representative at Cara, you’ll be at the forefront of driving growth with leading insurance agencies, brokerages, and wholesalers. You’ll be responsible for building and qualifying pipeline, managing inbound interest, and running highly targeted outbound campaigns for prospective customers.

You’ll engage executives and operations teams, understand their workflows and bottlenecks, and position Cara’s domain-specific AI as a way to streamline operations and boost premium production. Your ability to clearly communicate the value of Cara—paired with your rigor, ownership mindset, and interest in AI—will play a key role in shaping the future of work in insurance.

What You’ll Do

Build Pipeline: Create and manage a qualified pipeline of insurance agencies, brokerages, and MGAs aligned with Cara’s strategic customer profile using targeted outbound and personalized outreach.

Discovery & Qualification: Conduct initial discovery calls to understand current workflows, tools, service bottlenecks, and growth goals; run tailored Cara overviews to assess fit.

Collaborate Across Sales Team: Partner closely with the founders and Account Executives to evaluate qualified opportunities, provide product demos, and support follow-up activities to ensure smooth progression through the funnel.

Process & Playbook: Help build and improve Cara’s sales playbook—documenting talk tracks, email sequences, and learnings from the field.

Assess Gaps and Opportunities : Collect, aggregate, and organize feedback for the product team to deepen Cara’s value with new and existing segments, identifying opportunities for growth.

Event Support: Support pre- and post-event outreach for conferences, webinars, and industry association events; help convert event interest into qualified opportunities.

What You Have

1-2+ years of experience in a fast-growing startup or B2B environment, ideally in sales development, business development, or project/operations roles.

Strong executive presence and the ability to confidently engage agency principals, brokerage leadership, and senior managers.

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.