Top 10: Insurtech Leaders in North America
The insurance industry is experiencing a radical transformation with technology reshaping policy creation and claims management. Once resistant to change, the sector is now embracing digital innovation.
In this Top 10, we highlight the visionaries driving this revolution across North America’s insurtech landscape. These leaders are leveraging cutting-edge technologies to tackle longstanding challenges.
From start-ups to established firms, our list showcases a diverse group of innovators with backgrounds in computer science, actuarial studies and traditional finance. These leaders’ efforts are reimagining insurance for the digital age, setting new standards for efficiency and customer-centricity in a more accessible and personalised future.
10. Guy Goldstein
- Company: NEXT Insurance
- Position: CEO & Co-Founder
- Headquarters: California, USA
- Company founded: 2016
Guy Goldstein is the CEO and co-founder of NEXT Insurance, which he established in 2016 to revolutionise small business insurance. Under his leadership, the California-based company has secured over US$881m in funding and serves more than 400,000 customers. Goldstein's vision focuses on leveraging technology to simplify and personalise insurance for entrepreneurs. His industry experience includes founding Check, a mobile payment company acquired by Intuit, as well as serving as a major and fighter pilot in the Israeli Air Force.
9. Joshua Motta
- Company: Coalition
- Position: CEO
- Headquarters: San Francisco, USA
- Company founded: 2017
Joshua Motta, CEO and co-founder of Coalition, has revolutionised cyber insurance since 2017. His unique approach combines cybersecurity expertise with insurance coverage, creating an "active insurance" model that proactively protects clients. Under Motta's leadership, Coalition has secured US$755m in funding and achieved a US$5bn valuation. His diverse background, including roles at Cloudflare, Goldman Sachs and the CIA, informs Coalition's innovative strategy. Motta's emphasis on transparency, data-driven decision-making and a flat organisational structure has positioned Coalition as a leader in the rapidly evolving insurtech landscape.
8. Alex Timm
- Company: Root Insurance
- Position: Co-founder and CEO
- Headquarters: Columbus, Ohio, USA
- Company founded: 2015
Alex Timm, Root Insurance's CEO and co-founder, has steered the company to become a disruptive force in auto insurance since 2015. His data-driven approach, focusing on usage-based pricing, has challenged industry norms. Under Timm's leadership, Root has secured over US$800m in funding and successfully went public in 2020. Despite facing market challenges, Timm's strategic decisions have led to improved loss ratios and near-breakeven adjusted EBITDA. His commitment to fairness in pricing and leveraging technology for accurate risk assessment continues to drive Root's mission to transform the insurance landscape.
7. Mario Schlosser
- Company: Oscar Health
- Position: Co-founder and chief technology officer
- Headquarters: New York, USA
- Company founded: 2012
Mario Schlosser, co-founder of Oscar Health, has played a pivotal role in transforming the health insurance landscape since the company's inception in 2012. Initially serving as CEO, he recently transitioned to chief technology officer in March 2023. Under Schlosser's leadership, Oscar Health has grown to serve over one million members across multiple insurance products. His tech-centric approach has focused on leveraging data and personalised services to improve the healthcare experience. Despite facing challenges in the public markets, Schlosser's vision for a more transparent and consumer-friendly health insurance model continues to shape Oscar's strategy and the broader insurtech landscape.
6. John Clark Higgins
- Company: Steady Technologies
- Position: CEO & co-founder
- Headquarters: New York, USA
- Company founded: 2018
John Clark Higgins, co-founder and CEO of Steady Technologies, has been instrumental in driving innovation in property management and insurance since 2017. Under his guidance, Steady has created a sophisticated platform which delivers customised financial and insurance solutions for single-family rental property owners and managers. With a strong background in fintech, including roles at Prosper Marketplace, Higgins has successfully attracted over US$506m in investment. His focus on technological advancement and strategic partnerships positions Steady as a disruptive player in the insurtech landscape.
5. Sean Harper
- Company: Kin Insurance
- Position: CEO and co-founder
- Headquarters: Chicago, Illinois, USA
- Company founded: 2016
Sean Harper, co-founder and CEO of Kin Insurance, has been revolutionising the home insurance industry since 2016. Under his leadership, Kin has raised over US$410m in funding and grown to serve thousands of customers in catastrophe-prone areas. Harper's innovative approach combines direct-to-consumer sales with advanced technology, challenging traditional insurance models. Despite facing industry scepticism, Harper's strategic vision and commitment to fundamentals have driven Kin's success, earning it unicorn status and attracting high-profile investors.
4. Max Simkoff
- Company: Doma
- Position: CEO
- Headquarters: Miami, Florida, USA
- Company founded: 2016
Max Simkoff, Doma’s founder and CEO, has been reshaping the real estate closing process since 2016. His innovative approach applies machine learning to modernise the antiquated title insurance industry. Under Simkoff's guidance, Doma has expanded its reach to over 30 states, processing more than 800,000 real estate closings. Despite market fluctuations, his strategic pivot towards enterprise and purchase transactions has shown promising results. Simkoff's leadership style, emphasising technological innovation and operational efficiency, continues to drive Doma's mission to make homeownership more accessible and affordable.
3. Assaf Wand
- Company: Hippo Insurance
- Position: Co-founder and executive chairman
- Headquarters: California, USA
- Company founded: 2015
Assaf Wand, co-founder of Hippo Insurance, has been instrumental in reshaping the home insurance landscape since the company’s inception in 2015. As CEO until October 2022, he guided Hippo to raise US$1.3bn in funding and achieve unicorn status. Wand's focus on leveraging AI and data analytics enabled proactive protection and simplified coverage for homeowners. His background in finance and commitment to innovation informed Hippo's strategy. Now serving as executive chairman, Wand continues to influence Hippo's mission to modernise home insurance through technology and data-driven insights.
2. Daniel Schreiber
- Company: Lemonade
- Position: Co-founder and CEO
- Headquarters: New York, USA
- Company founded: 2015
As the co-founder and CEO of Lemonade, Daniel Schreiber has been a transformative force in the insurance industry since 2015. His vision of leveraging AI and behavioural economics has redefined insurance, offering instant policies and claims processing. Under Schreiber's leadership, Lemonade has raised over US$480m, achieved unicorn status, and successfully went public in 2020. His innovative approach includes the Giveback program, where unused premiums are donated to charities. Despite market challenges, Schreiber's commitment to transparency and social good continues to drive Lemonade's growth.
1. John Swigart
- Company: Pie Insurance
- Position: Co-founder and CEO
- Headquarters: Washington, USA
- Company founded: 2017
John Swigart, co-founder and CEO of Pie Insurance, leads the company as a transformative force in the insurtech industry, securing US$615m in funding since its establishment in 2017. This innovative powerhouse specialises in workers' compensation insurance for small businesses, expanding its services across 38 states and Washington D.C. Pie’s success is rooted in its data-driven approach, which accurately prices risks and streamlines the insurance process. With over 400 employees, Swigart’s extensive background, including 13 years at Esurance, informs Pie's tech-driven strategy. Recognized as the 2020 Mid-Atlantic Entrepreneur of the Year, he continues to position Pie as a disruptive leader in the sector.
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