Insurtech Remote Jobs in Wisconsin (NOW HIRING)

Are you an experienced insurance sales professional and excited to use your deep expertise in developing packaged casualty offerings? Do you enjoy working directly with brokers and clients while quarterbacking complex insurance sales cycles from first conversation through bind and renewal?
Understory is looking for a VP, Casualty Insurance to support new business development and client relationships across our growing P&C insurance portfolio. This is an individual contributor role focused on insurance sales, driving deal execution and consistently hitting or exceeding quota expectations.
This role is ideal for someone with significant insurance or insurtech experience who wants to build and lead our Casualty offering.
Your Main Responsibilities Will Include

• Support new business sales efforts across P&C insurance products, including prospect research, outreach, meeting preparation, and follow-up.
• Work closely with other members of the sales team, along with our underwriting and product leaders to identify and move deals through the pipeline.
• Manage broker and client communications, including scheduling meetings, preparing materials, and responding to inbound questions.
• Drive the end-to-end complex sales process, from initial introduction through quote, bind, and renewal.
• Maintain accurate pipeline tracking and documentation in CRM systems (Salesforce).
• Analyze underwriting considerations, pricing, and risk structures to develop client-facing solutions.
• Support renewal and expansion efforts by preparing performance summaries, coverage updates, and renewal materials.
• Develop a strong foundational understanding of Understory's products, value proposition, and target customer segments.

You're Exactly the Person We're Looking For If You

• Have 8+ years of experience in insurance, insurtech, or a client facing brokerage role specializing in commercial business
• Have deep experience with property & casualty insurance sales, consistently hitting or overachieving on sales goals and quota
• Preference towards candidates with Captive, E&S, Dealer Open Lot or Parametric experience
• Are comfortable managing longer, complex and high premium sales 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 comfortable working in a fast-moving startup environment with evolving processes.
• Have experience using CRM tools or sales systems (Salesforce)
• If you are local to Madison, we work a Hybrid schedule. For remote candidates, travel to HQ will be expected for team trainings, get-togethers and
• Ability to travel for customer meetings and industry conferences up to 50%

Compensation Includes

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

About Understory
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.