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Questpro

Questpro

via LinkedIn

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Head of Property Underwriting (Habitational, Condo, HOA)

Anywhere
Full-time
Posted 2/19/2026
Verified Source
Key Skills:
Technical Troubleshooting
Windows/Linux Systems
Storage Area Networks

Compensation

Salary Range

$Not specified

Responsibilities

Lead underwriting product development and team building in the HOA/Condo insurance sector.

Requirements

7-10+ years in property underwriting with strong broker relationships and entrepreneurial mindset.

Full Description

Job Title Head of Underwriting • Role & ResponsibilitiesDevelop initial products, appetite & advanced underwriting framework for launch • Stand up early broker distribution playbook • Establish capacity and reinsurance architecture (w/ help from the executive team and a reinsurance broker) • Make strategic underwriting hires and build underwriting team • Ideal Background7–10+ years in Property Underwriting within the HOA / Condo / Habitational / Community Association segments • Strong relationships with West Coast retail and wholesale brokers (especially in CA, AZ, NV, OR, WA) • Entrepreneurial mindset - thrives in start-up or “whiteboard” environments • Familiarity or appreciation of Insurtech platforms, real-time data, and tech-enabled risk assessment • Excellent communication and leadership skills; capable of building a team over time • Comfortable with risk/reward and motivated by equity participation and long-term upside • (Nice to have) Proven ability to design product, rate plans and underwriting guidelines • (Nice to have) Experience securing carrier capacity, reinsurance or delegated authority agreements • Personality & DNABuilder. Connector. • Energized by autonomy and ownership. • Knows the market and has the relationships to bring early traction. • Sees how technology and underwriting can combine to disrupt a niche. • Passionate about expanding access to affordable insurance in catastrophe-prone states. • Operates with a data-first mindset in decision-making

This job posting was last updated on 2/23/2026

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