Sales Associate; P&C Insurance

Are you early in your insurance sales career and excited to sell deep expertise in property & casualty products? Do you enjoy working directly with brokers and clients, learning how deals get done, and supporting complex insurance solutions from first conversation through bind and renewal?

Understory is looking for a Sales Associate to support new business development and client relationships across our growing P&C insurance portfolio. This is an individual contributor role focused on learning the fundamentals of insurance sales, driving deal execution, and developing the skills needed to grow into a more senior commercial role over time.

This role is ideal for someone with early insurance or insurtech experience who wants hands‑on exposure to broker relationships, underwriting collaboration, and consultative sales in a fast‑growing, mission‑driven company.

• Support new business sales efforts across P&C insurance products, including prospect research, outreach, meeting preparation, and follow-up
• Work closely with senior sales, underwriting, and product leaders to help move deals through the pipeline
• Assist with broker and client communications, including scheduling meetings, preparing materials, and responding to inbound questions
• Drive the end‑to‑end sales process, from initial introduction through quote, bind, and renewal
• Maintain accurate pipeline tracking and documentation in CRM systems (Salesforce)
• Learn how underwriting considerations, pricing, and risk structures translate into client‑facing solutions
• Support renewal and expansion efforts by helping prepare performance summaries, coverage updates, and renewal materials
• Develop a strong foundational understanding of Understory’s products, value proposition, and target customer segments
• Grow over time into more independent ownership of smaller deals or defined segments of the sales process.

• Are willing and able to work a Hybrid schedule (2‑3 days per week) in our Madison, WI office. We are not currently open to F/T remote or relo candidates for this role.
• Have 2–3 years of experience in insurance, insurtech, or a client facing brokerage role
• Have exposure to property & casualty insurance concepts (through sales, underwriting support, account management, or brokerage)
• Are interested in building a long‑term career in insurance sales and learning consultative, complex deal cycles
• Are organized, detail‑oriented, and comfortable managing multiple deals or accounts at once
• Communicate clearly and professionally with brokers, clients, and internal teams
• Are eager to learn, ask questions, and take feedback
• Are comfortable working in a fast‑moving startup environment with evolving processes
• Have experience using CRM tools or sales systems (or are excited to learn)

• Base salary commensurate with experience
• Variable compensation tied to sales performance
• Full‑time benefits package
• Equity package

Understory is a leading provider of insurance solutions built for the era of climate change. The company’s global network of Dot weather stations powers the world’s most sophisticated weather risk model. By combining mutualized, optimized risk structures with precision weather technology and modeling, Understory develops affordable, stable property insurance solutions.

Traditional insurance is no longer fit for purpose. Natural catastrophes driven by the volatility of climate change are increasing rates and restricting coverage. Insurance and reinsurance companies are pulling out and leaving vast portions of the world’s assets unprotected. Transformation is inevitable — and Understory is building what comes next.