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Executive Vice President of Insurance Division

The Jacobson Group
Midwest, WY Full Time
POSTED ON 5/18/2026
AVAILABLE BEFORE 6/16/2026

Job Description:
A fast-growing insurtech is seeking an Executive Vice President, Insurance Division. The EVP will lead the insurance division and take full ownership of a premium business spanning renters, travel, damage protection, and adjacent insurance products across residential and short-term rental markets. This executive will oversee two core operating divisions, aligning their strategies under a unified vision while ensuring each continues to perform and scale within its distinct market focus. In this role, the EVP will shape and execute the next phase of growth by expanding revenue, launching new products, and scaling a digitally enabled insurance platform embedded across a fast-growing ecosystem. This executive will operate with true enterprise scope, building a modern AI-enabled insurance organization; optimizing performance across underwriting, service, and operations; and leveraging direct carrier relationships within a flexible MGA-like model to accelerate speed and innovation. This is a retained search.

Responsibilities:

  • Strategy, Growth and P&L Leadership - Own the strategy, growth agenda, and full P&L, including revenue expansion, market penetration and product innovation. Leverage deep industry expertise to identify new business models, distribution opportunities, and strategic partnerships, while setting annual plans, KPIs and representing the division at the enterprise level.

  • Go-to-Market, Product and Pricing Strategy - Lead integrated go-to-market execution across sales, marketing and product. Build a scalable revenue engine, optimize pricing and carrier partnerships, and guide product roadmap prioritization in collaboration with technology and customer advisory groups.

  • Leadership and Compliance - Build and lead a high-performing leadership team and culture focused on accountability and execution. Ensure strong regulatory compliance across all operations while fostering talent development and organizational alignment to growth objectives.

  • Operational Excellence and Digital Transformation - Build a scalable, efficient operating model across underwriting, service and back-office functions. Drive AI and automation to improve performance and customer experience, partnering with technology leadership to align execution with strategy.

  • Customer Growth and Distribution Expansion - Drive retention, expansion and new channel growth across PMC, STR, and alternative distribution partners. Strengthen onboarding and service delivery while building lifecycle-based insurance offerings that deepen policyholder relationships.


Requirements:

  • 10 years of senior leadership experience in the insurance industry, ideally with full P&L ownership and exposure to software or SaaS-enabled organizations

  • Proven success scaling revenue and operations in a high-growth insurance environment, including managing general agency or MGA-like models

  • Demonstrated experience leading cross-functional roles such as sales, marketing, client success, account management and operations

  • Strong financial acumen with experience managing P&L, budgets, KPIs and strategic planning in a data-driven environment

  • Deep knowledge of insurance regulations and compliance frameworks, particularly in digitally enabled or embedded insurance workflows

  • Experience operating within complex enterprise environments and managing relationships with executive leadership and boards of directors

  • Bachelor’s degree in business, risk management, insurance, or related field; Master’s degree and/or professional insurance designations such as CPCU (preferred)

  • Licensed insurance producer or ability to obtain licensure within 90 days of hire

Salary.com Estimation for Executive Vice President of Insurance Division in Midwest, WY
$206,715 to $291,011
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