Published December 20, 2023

Three Traits Legacy Insurance Executives Can Bring to the Insurtech Industry

As the $5.48 Billion Insurtech industry continues to grow—by a projected $140 Billion before 2030—the infusion of seasoned talent becomes crucial to navigate the evolving challenges and opportunities. Legacy insurance executives, armed with a wealth of experience and deep industry knowledge, stand as key players in steering Insurtech companies toward success.

In the early days of Insurtech, the prevailing thought was to target talent outside the insurance industry, as highlighted by Dave Wechsler, Principal at OMERS Ventures and a lead Insurtech investor. However, the tide is shifting towards executives with incumbent carrier experience, with Wechsler noting, “Now I would say it’s heavy on insurance with enough tech to ensure the potential for differentiation.”

Emilio Figueroa, CEO and founder of Indemnity Lab, LLC, emphasizes that now investors see the benefits of infusing legacy insurance experience into Insurtech leadership. “Insurance leaders have to take different approaches to be successful in this highly competitive industry,” he says. “It’s like being a seasoned chef in a fusion kitchen, you have to know the classic recipes by heart before you start experimenting with new flavors and techniques.”

Jacob Galecki , Managing Principal at Galecki Search Associates, observes, “Executives who bring specialized expertise to the table are certainly in demand across insurance and insurtech—particularly people with cyber, climate, and ESG backgrounds, or experience in specific industry segments like construction, energy, and agribusiness. But having a solid foundation in the insurance fundamentals—underwriting, actuarial science, risk management, and claims—is now a must-have, even for the tech-enabled insurers.”

Successful Meeting

Galecki Search Associates identifies these top three traits that insurance leaders with traditional backgrounds can bring to Insurtech:

  1. Profitable Book/P&L Management: Wechsler stresses the importance of running a sound book of business, citing its priority value as Insurtech investing evolves. “Tech investors are used to finding the equation for profitability down the road: acquire customers first (at a loss is fine) and then master-mind your profitability strategy,” he says. “And it works when customers have long lifetimes. You lose money upfront but know that over time there will be profitability. We have learned this does NOT work in insurance where other people (i.e. the reinsurer) take the loss. So it’s critical that people who understand how to build a good book are in the driver’s seat. Understanding the nuances of achieving a target combined ratio, containing the loss ratio, and maintaining underwriting discipline provides Insurtech leaders with a distinct competitive advantage.
  2. Risk Management and Underwriting Expertise: Legacy insurance executives excel in risk management, bringing decades of experience in assessing, pricing, and mitigating risks. This expertise is crucial in the Insurtech sector, where innovation often outpaces the development of standardized risk evaluation methods. “A good underwriter is akin to a skilled strategist, blending analytical acumen with risk vigilance,” points out FIgueroa. “A great underwriter discerns subtle risks, makes predictive judgments, and uses gut feelings, honed by experience, that safeguard the company’s interests and risk appetite.” This expertise is particularly critical in the Insurtech space, where innovation often outpaces the development of standardized risk evaluation methods. “While books need time to season, it’s critical to show a path to profitable underwriting,” says Wechsler. “And this achievement isn’t only driven by underwriting, it’s a function of all disciplines working well together.”
  3. Industry Relationships and Networks:Building and maintaining strong industry relationships is a hallmark of successful insurance executives, and this trait is highly transferable to the Insurtech space. Legacy executives often have extensive networks that can give Insurtech startups a competitive edge. “You can’t completely march to the beat of your own drum when you need to partner with so many others, like fronting carriers, reinsurers, TPAs,” says Wechsler. “Now we like to see leaders who understand how the ecosystem works and the potential impact of big decisions. In the early days, we were excited about ‘disruption’ and taking a very different approach [to Insurtech leadership]. That isn’t because we had issues with the way incumbents worked—it was more about finding venture returns. Subsequently, we have learned that, in insurance, it’s hard to break too far outside of the mold since the ecosystem is so reliant on all members.”

Bonus Skill–Comprehension of Regulatory Environment:Navigating the complex regulatory landscape—let alone sorting out state filings to be able to market a product—is a challenge for any player in the insurance industry. Legacy executives bring a wealth of regulatory acumen to the table. Their innate understanding of compliance requirements, legal frameworks, and industry standards is indispensable for Insurtech firms seeking to disrupt traditional models.


Legacy insurance executives offer a unique blend of experience, expertise, and relationships to the Insurtech industry. As the Insurtech industry continues to evolve, collaboration between legacy executives and tech-savvy entrepreneurs holds the key to shaping a future where the best of both worlds converge, for the health of the industry and for its obligation to the policyholders of today—and tomorrow.

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