Ledgebrook is hiring an Associate / Manager, Strategic Initiatives to help shape the future of a fast-growing, tech-enabled Specialty insurance company.

This is a high-impact opportunity for someone who thrives at the intersection of strategy, operations, data, and execution.

You’ll partner across underwriting, analytics, engineering, operations, legal, and executive leadership to drive critical company initiatives including:

• New product launches

• Data and technology initiatives

• Enterprise change management

• Executive and board-level strategic presentations

• Cross-functional project leadership

We’re looking for someone who can bring structure to ambiguity, influence across teams, and help move big initiatives forward in a fast-paced environment.

What stands out:

• Meaningful ownership from day one

• Remote-first and flexible working

• Competitive compensation + equity

• Exposure to senior leadership and strategic decision-making

• Collaborative, high-talent-density culture

Ideal background:

• Property & Casualty insurance experience

• Strong project management skills

• Comfortable working with insurance data and reporting

• Excellent PowerPoint and executive communication skills

• Strategic and analytical mindset

At Ledgebrook, we’re building a modern E&S insurance company powered by deep underwriting expertise and technology built for the future.

If you’re excited by building, solving problems, and helping scale something special — we’d love to connect.