Business and Revenue Operations Lead

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 our Business and Revenue Operations Lead, you will build and scale the operational infrastructure behind Cara’s growth engine.

You will work across Sales, Customer Success, Finance, Legal, and Leadership to improve how Cara manages deals from initial opportunity through contracting and expansion. You will own critical workflows across revenue operations, quote-to-cash, forecasting, billing, and business reporting.

This is a highly cross-functional and hands-on role for someone who combines analytical rigor with a strong operating mindset. You will help establish the systems, processes, and reporting infrastructure Cara needs to scale efficiently as our customer base, revenue, and team continue to grow.

What You’ll Do

• Own and improve Cara’s quote-to-cash processes across quoting, contracting, billing, renewals, and expansions

• Build and maintain reporting across pipeline, ARR, renewals, expansion, and revenue performance

• Support revenue forecasting, billing reconciliation, budgeting, and company planning

• Improve data quality, automation, and process consistency across HubSpot, billing systems, and related tools

• Coordinate bookkeeping and audit readiness with external specialists

• Run selected cross-functional initiatives where financial analysis and judgment are central to decision-making

What You Have

• 2+ years of experience in revenue operations, business operations, strategic finance, or a related role

• Experience working in a high-growth B2B SaaS or AI technology company

• Strong understanding of recurring revenue models, quote-to-cash workflows, and SaaS metrics such as ARR, renewals, and expansion

• Advanced Excel or Google Sheets skills, with experience building reliable financial models, forecasts, and operating dashboards

• Experience with HubSpot, billing platforms, or similar business systems

• Exceptional analytical ability, attention to detail, and a builder mindset—you identify problems and implement solutions