About Us
We are building the Insurance Carrier of the Future—a licensed, modern insurance company based in New York. Our mission is to redefine what it means to be an insurance carrier in the 21st century by leveraging AI, automation, and innovative product design to deliver better business outcomes – scale, efficiencies, accuracy and customer experience.
The insurance industry will necessarily change more in the next 10 years than in the last 100—and we intend to lead that revolution. See here our Insurtech 2.0 manifesto.
We have identified a fully-funded home-insurance carrier that we intend to acquire and turn into a multi-line modern carrier. Backed by visionary investors, renowned technologists and supported by deep regulatory expertise, we are now looking for the right person to take the helm.
The Opportunity
We’re seeking a Founding CEO who is equal parts visionary, operator, and builder. You will be the strategic and cultural cornerstone of the company—leading product innovation, go-to-market strategy, team building, and operational execution.
Compensation will be large double-digit equity package with standard vesting
Significant cash compensation based on performance
What You’ll Do
- Vision for a radically different kind of insurance company—tech-forward, agile, and customer-obsessed
- Build founding team, attracting top talent across product, engineering, underwriting, claims, operations, and growth
- Execute and scale the business with capital efficiency, and strategic creativity
- Collaborate with regulators and reinsurers to ensure innovative products and models align with evolving compliance standards
- Leverage best-of-breed AI tools, automation, and data to reduce friction, improve pricing, and delight customers
- Establish culture with a long-term mindset and clear milestones
What We’re Looking For
- Proven track record as a founder, senior operator, or C-level exec in a high-growth startup (traditional insurance, insurtech or fintech)
- Deep insurance expertise
- M&A and Integration experience is helpful, but not fully necessary
- Technologically fluent— you grasp how data and automation can create business advantages
- Entrepreneurial, scrappy, resourceful, resilient, and relentlessly execution-oriented
- Exceptional leadership and communication skills with the ability to inspire and rally teams, partners, and investors
- Comfortable navigating regulated environments and complex ecosystems
- New York-based or willing to spend significant time in New York
Why Join Us?
- Equity upside: Large double-digit equity stake in the company
- Performance-driven compensation: Strong cash package tied to milestones and growth
- Blank canvas: Build something meaningful from day one with real resources, licensing, and support
Contact:
teddy @ optimist.vc