Interview with Neil Mitchell: From Insurance Executive to Insurance Entrepreneur

Neil Mitchell

Toronto area entrepreneur and businessman Neil Mitchell has more than three decades of insurance brokerage experience, with expertise in Risk Management, Property & Casualty Insurance and Insurtech.

Following a successful corporate insurance career, Neil shifted his focus to entrepreneurship. In 2018, he personally funded and co-founded a startup venture called Players Health, a company specializing in insurance solutions and risk management services for youth athletes and sports organizations. As an early-stage and Series A investor in Players Health, Neil raised capital from angel investors and venture capitalists, identified and hired talent, developed partnerships with brands, secured re/insurance capacity, originated insurance products, and built revenue-producing client relationships.

Q: What inspired you to transition from being an insurance executive with a rewarding career working for Marsh, a large corporate insurance brokerage, to personally fund, co-found and raise venture capital for a startup insurance venture?

NEIL MITCHELL: My entrepreneurial interest was piqued in 2010/2011 while working at Marsh. At that time, the term insurtech was not broadly known and any interest in this subject was embedded in the broader fintech sector. Very few insurance organizations had made any serious investments in creating and scaling digital road maps with respect to the collection, analysis, and use of data to drive product development, optimize underwriting operations or improve the customer experience. As I journeyed through various roles in client management, sales and distribution, strategy, operations, and product development, I saw increasing opportunities to streamline operations, enhance customer experiences, create insurance solutions using embedded risk management services, and scale sales and distribution using technology. Entrepreneurial ideas began to develop as I met insurance executives, insurance entrepreneurs, individual investors, and VCs. These interactions provided valuable insights into client pain points that could be addressed with innovative insurance and risk management solutions underpinned by technological tools funded by angel investors and venture capital.

Q: What were some of the biggest challenges you faced in starting Players Health and how did you overcome them?

NEIL MITCHELL: One of the biggest challenges was a personal one. I moved from a corporate environment with access to and the support of countless resources to an environment of scarce resources, self-sufficiency, taking on personal financial risk, and deferring any form of financial gratification in the hope of a meaningful return at some point in the future. My new reality was unlike my life as a corporate employee who was well compensated and rewarded, and who had operated with a lot of support, resources, structure, and stability. Corporate and entrepreneurial environments are shaped by different work responsibilities and realities.

As an entrepreneur running a startup, one must literally “burn all the boats” and be “all in” with their time, personal finances, their network, and their resources. There is no safe place. There will be changes and pivots, but no safety net.

Q: What advice would you give to someone looking to transition from a long-time corporate career to create and build a startup venture?

NEIL MITCHELL: Identify the problems, gaps, inefficiencies, and pain points facing your industry. Use your personal experiences, industry knowledge, as well as that of industry peers to validate pain points. Identify if your solution really represents a sizable, addressable market. Stay focused on your solution and avoid the many shiny objects that will undoubtedly come your way. Pivots and changes will occur only after you have market tested your hypothesis. Customer feedback will be the ultimate litmus test for your solution. As you gain customer feedback, be quick to embrace failure, and then pivot to a new or evolving opportunity. You’re also going to need a network of well-intentioned mentors and advisors who can provide access to growth capital, guidance, advice, support, and the tough love required to help you avoid making costly mistakes. As an entrepreneur, you’ll be responsible for every aspect of the business. Unlike working in a corporation, the risks and the rewards fall squarely on your shoulders. It’s important to be comfortable with uncertainty. Build contingency plans and maintain financial reserves to handle unexpected challenges. Control your “burn”.

Be prepared to embrace, accept, and adapt to the constant changes that you will experience. How you start will not be how you finish or exit the venture.

Q: How has the insurtech sector evolved for startups?

NEIL MITCHELL: The sector continues to evolve. It is much more informed, measured, and mature than in its early days. Investors today are now much more focused on profitability as opposed to so-called “disruptive income” hypotheses, collaboration versus disruption, and teams composed of outsiders and insiders versus just a team of outsiders. Investors are less inclined to fund shiny objects with little to no revenue, no validated product market fit, the absence of a reasonable path to profitability, and no insurance industry experience. Today’s investment environment necessitates startup founders be creative yet pragmatic in the use cases they pursue. The successful startups will be those that have teams composed of young, smart, and creative innovators, including experienced industry professionals who bring their wisdom and “been there done that, seen it before, don’t do it” experience, and who possess deep domain experience, industry relationships, and networks.

Q: With the rise of more insurtech ventures, how do you view the evolving competitive landscape, especially concerning incumbent insurance organizations?

NEIL MITCHELL: The increasing number of insurtech ventures underscores the importance for incumbents to digitize their business operations. Many incumbents are well on their way to developing digital road maps and implementing practical use cases. I see the marketplace as being more about collaboration; not disruption. We’re seeing more partnerships and service contracts between insurtech ventures and incumbents using new technologies and innovative business models. Incumbents are seeking to build, buy, partner, and invest in these ventures. They are less concerned about a competitive threat. Together, these two groups are using, developing, and scaling mutually beneficial, digital-first solutions. This cooperation is bringing significant improvement and innovation to products, distribution, operations, and consumer services and experiences. With the dawn of Generative AI, we’re going to see greater interest and demand by incumbents to collaborate with emerging AI based Insurtech ventures. These collaborations provide incumbents with access to highly skilled talent, new business models, and innovative technologies that will help them accelerate their own technological adoption and advancement.

Q. What are some of the critical things entrepreneurs need to know about their competition before launching their startup?

NEIL MITCHELL: There are several things startup founders need to know about their competition.

  1. Understand who the incumbents are in their target market: Do they have a unique value proposition? If so, what is it? Do they have an advantage versus others in their market? What is that advantage? Have they established any type of “moat” or barrier to entry that makes it hard for competitors and new entrants to compete for their business?
  2. Have would-be competitors tried to enter the target market before? Who were these competitors? Did they flame out? If yes, why and how did they flame out?
  3. Research the businesses in adjacent sectors who could wake up and make a play for your target market. Don’t underestimate this possibility.

Q: Earlier, you referred to customer feedback. What role does that play in the development and growth of start-up ventures?

NEIL MITCHELL: Customer feedback is everything. It is the foundation to achieving a good product market fit. When you launch a product or service in the marketplace, the first thing you should be eagerly seeking out is customer feedback. You have to be constantly vigilant and attentive to the customer experience and listening to customer feedback. Creating lines of communication and engagement with customers early on ensures you’re addressing their needs quickly and optimizing business opportunities for your startup.

Startups frequently enter a market with an innovative product or service, but with little in the way of customer validation. It’s critical that the startup solves a real problem for customers that is scalable. Customer feedback validates whether the product or service meets the intended needs. It can also highlight areas that need improvement or refinement.

Early customer feedback allows startups to make adjustments, improvements, and at times, major pivots from the original product or service offering. This ensures that the product evolves in ways that satisfy the customer. It can also prevent wasting time, money, and resources on features customers don’t need or really don’t care about.

I can’t underscore enough how important customer feedback is for founders and their startups, as it drives product development, improves customer experience, helps identify new market opportunities, and enhances customer loyalty. All of these elements are critical for securing product market fit and building a startup into a business with a scalable and profitable future.

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