Customer Success

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 a Customer Success Manager at Cara, you’ll be responsible for ensuring agencies and brokerages successfully adopt and expand their use of Cara after the sale. You’ll own the customer journey from onboarding through renewal, working closely with clients to drive measurable impact across servicing, sales, and operational workflows.

This is a high-impact role where you’ll be on the front lines helping agencies and brokerages operationalize AI within their organizations. You’ll collaborate directly with the founders and product team, shape the post-sale motion, and play a critical role in Cara’s growth story.

What You’ll Do

• Customer Onboarding & Implementation: Lead successful rollouts of Cara, ensuring seamless integration into client workflows.

• Adoption & Enablement: Train producers, account managers, and servicing teams to embed Cara into their daily workflows and maximize value from the platform.

• Customer Relationship Management: Serve as the primary point of contact post-sale, building strong relationships with both executive stakeholders and frontline users to drive long-term partnership.

• Customer Support & SLA Management: Manage inbound customer support requests, triage tickets, handle customer inquiries and feature requests, and ensure timely resolution in accordance with defined SLAs. Partner with engineering to prioritize and resolve issues efficiently.

• Customer Health & Retention: Monitor usage, adoption metrics, and feedback to proactively manage customer health, ensure renewals, and identify expansion opportunities.

• Product Feedback Loop: Partner closely with product and engineering to relay customer insights, influence roadmap priorities, and continuously improve the customer experience.

What You Have

• 2+ years of experience in Customer Success, Solutions Consulting, or a similar client-facing AI, SaaS, or fintech role.

• Proven ability to manage customer relationships and drive adoption in a high-growth environment.

• Strong ability to translate complex technology into clear operational and business value.

• Excellent communication and relationship-building skills across both executives and operational teams.

• Highly organized and able to manage multiple accounts simultaneously.

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

• Bonus: Experience working with insurance agencies, brokerages, or financial services organizations. Experience with AI, automation, or vertical SaaS products.