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Insurtech Sales Jobs in Wisconsin (NOW HIRING)

Director of Marketing

Madison, WI · On-site +1

  • Medical

  • Dental

  • Vision

  • Retirement

From shaping brand and product messaging, to building demand generation programs, to enabling sales ... in the insurance or insurtech sectors - preference towards individuals with experience in ...

Insurtech Sales information

What is the difference between Insurtech Sales vs Insurance Sales Agent?

AspectInsurtech SalesInsurance Sales Agent
CredentialsSales experience, knowledge of insurtech productsInsurance license, sales experience
Work EnvironmentTech-driven, digital platforms, remote optionsIn-person, agency offices, client meetings
Employer & IndustryInsurtech companies, startups, tech-focused insurersInsurance agencies, brokerages, carriers

Insurtech Sales professionals focus on selling innovative insurance technology solutions, often working remotely and leveraging digital tools. In contrast, Insurance Sales Agents typically sell traditional insurance policies through in-person interactions and require licensing. Both roles involve sales skills and industry knowledge but differ in environment and product focus.

What are some common challenges faced in an insurtech sales role, and how can they be addressed?

A common challenge in Insurtech Sales is navigating the fast-paced evolution of insurance technology and effectively communicating its value to clients who may be unfamiliar with digital solutions. Sales professionals often need to stay updated on industry trends, regulatory changes, and emerging competitors. Building trust with traditional insurance clients and demonstrating how technology can improve efficiency or customer experience is essential. Collaboration with product, marketing, and technical teams is key to providing tailored solutions and ensuring client needs are met.

What is insurtech sales?

Insurtech Sales refers to the process of selling insurance products and services that are enhanced or enabled by technology innovations. Professionals in this field work with digital platforms, data analytics, and other tech-driven tools to connect customers with insurance solutions more efficiently. Their role often involves educating clients about new insurance technologies, streamlining the purchasing process, and fostering relationships with both traditional insurers and tech startups. Insurtech salespeople need a strong understanding of both insurance fundamentals and the latest technological trends in the industry.

What are the key skills and qualifications needed to thrive as an insurtech sales professional?

To thrive as an Insurtech Sales professional, you need a strong understanding of insurance products, industry trends, and sales techniques, often supported by a bachelor’s degree in business, finance, or a related field. Familiarity with CRM platforms, digital sales tools, and insurtech software solutions is essential for managing leads and demonstrating product value. Excellent communication, relationship-building, and adaptability are crucial soft skills that help foster trust and respond to evolving client needs. These competencies enable sales professionals to effectively connect innovative technology with customer requirements, driving growth in a competitive market.
What are popular job titles related to Insurtech Sales jobs in Wisconsin? For Insurtech Sales jobs in Wisconsin, the most frequently searched job titles are:
What cities in Wisconsin are hiring for Insurtech Sales jobs? Cities in Wisconsin with the most Insurtech Sales job openings:
Infographic showing various Insurtech Sales job openings in Wisconsin as of August 2026, with employment types broken down into 100% Full Time. Highlights an 46% In-person, and 54% Remote job distribution.

Vice President (Casualty Insurance)

Understory

Madison, WI • On-site

Full-time

Re-posted 22 days ago


Job description

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.