Three years into the 2020’s: Taking Stock of the Decade’s Insurtech Predictions (Part 2)

I hope you enjoyed Part 1 of this article.  This post covers Trends 5-7 from my 2020 article and some Bonus ones for the rest of the decade.

Trend #5: Macro Economy – Roaring 20s into the Great Depression

From 2020 article:

In the 1920s – The stock market crash of October 1929 began the period known as the Great Depression.

In the 2020sMany (including me) think a correction is on the way. As I’ve mentioned in my predictions in years’ past, a correction may stymie some of the investments in innovation we’ve seen over the past several years.

Three Year Reflection and 2023 Thoughts:

During the last few years, stock markets have been all over the place, interest rates and inflation have been on the rise, and individuals have become millionaires and/or poor off of cryptocurrency and meme stocks.

While I was correct about a market correction coming, While some of the publicly traded insurtech’s stock prices have suffered, I was not fully correct on the ‘stymie’ in investments in insurtech that would result out of it.

Image Sources:  and Gallagher Re Global Insurtech Report November 2022

Despite this, we’ve still seen an upward trend in insurtech investments.  Many of my investor friends say that this has been the best time to invest as many have capital yet to be deployed from previous fund raises and valuations have also come down to more attractive levels than their peaks in 2017/2018.  Further, firms are placing larger investments on more later stage rounds on proven solutions and continue to place seed money for truly new/revolutionary ideas.

I don’t see an end in sight to market, interest rate and/or inflation volatility.  At the same time, I also don’t see a slowdown in interest in investing in insurtech and I feel that there will be more continued investment in insurtechs enabling incumbents and agents rather than those competing with them.  Does something have to give?  I’m not so sure now and we’ll see how this plays out in the years to come…

Trend #6: The Nature of Work

From 2020 article:

In the 1920s – In May 1926, ”Ford Motor Company becomes one of the first companies in America to adopt a five-day, 40-hour week for workers in its automotive factories.”

In the 2020sAs an increasing number of individuals seek more flexibility in the way they work, as technology continues to evolve, and as the working community continues to challenge the mold of the five-day, forty-hour work week, we’ll see similar advances and shifts in insurance.

Three Year Reflection and 2023 Thoughts:

With many of the changes coming out of the pandemic noted above, none was more impactful than that on the nature of work.

We’ve seen business travel and remote working change, ‘The Great Resignation’ and ‘Quiet Quitting’, which both ultimately focused on an individual’s desire for more work/life balance and has also resulted in changes to what benefits people value from their employer, as well as how an individual can promote themselves differently than before to potential employers.

In addition, we’ve seen an abundance of tech layoffs from both from big tech and start-ups, and may companies starting to freeze hiring at the end of this year to ‘see what happens in 2023’.

Coverager’s Year in Review1 and a recent article from Adrian Jones2 have highlighted these layoffs (links at bottom of article) and as recently as last week we saw a massive round of layoffs at Salesforce and Amazon.

What does this all mean?

  • More companies are going to need to be flexible in the way they engage talent. As a remote worker for the past 5 years, I know the immense value of face-to-face interaction with my colleagues.  I also know that I don’t need to see them every day and can be massively productive at the home of my choosing.  Many people think like I do in this respect, and it provides a massive opportunity for companies that embrace this to hire talent that they may have not had access to in their immediate vicinity.  While some jobs require on premise, many, especially in insurance, do not (at least not all the time).
  • Building on this, the types of benefits that employees desire have changes. According to a report by Zenefits that surveyed over 300 businesses3, employers are starting to see a rise in things like physical health (gym), mental health, pet insurance and financial wellness as additional benefits employees would like in addition to their normal health and retirement benefits.  We’ve seen some companies like Walnut, Goalsetter, Optimity and many others that have been successful in offering solutions in this space, and we’ll continue to see more.
  • Lastly, I’ve seen more companies be open to the concept of hiring fractional executives to help run their business and the emergence of companies/individuals promoting themselves as fractional executives. While the concept of fractional has been around for a while (I was first exposed to fractional CFOs), seeing companies like Propel and Brilliantly SaaS launch in 2022 is a trend I expect (and hope) to see more of throughout the rest of this decade.

Trend #7: Mass Media/Communications

From 2020 article:

In the 1920s – Mass media was born in the 1920s…In November 1920, the first commercially-licensed radio station began broadcasting live results of the presidential election… television was invented towards the mid-1920s, providing another means of communication for the masses.

In the 2020sFacebook, Twitter, YouTube, smartphones, the Internet…How many methods of communication do we have today? The number of outlets available to connect with individuals has changed the way the insurance industry markets to and engages with its policyholders. The insurance industry will need to embrace and specialize within these evolving communication methods if it wants to stay relevant in the 2020s and beyond.

Three Year Reflection and 2023 Thoughts:

Selling insurance through social media is hard, hence why many of the insurers and insurtechs mentioned in Trend #1 have focused on working with agents (lower cost of acquisition).  Regardless, insurers, insurtechs and agents will need to continue using social media as a means of brand awareness and lead gen.

With the emergence of new social media apps like Tik-Tok, BeReal and Mastadon, along with the interesting times over at Twitter, all three of the players mentioned above will need to stay abreast of the apps that people tend to favor and make sure they are allocating their marketing and distribution dollars accordingly.


I must shout out Jake Tamarkin and the folks at Every Day Life Insurance for amassing 150k followers on their Tik Tok with one of their posts having 9.3m views!

Bonus Trends

From 2020 article:

Mickey Mouse first debuted in 1928 in “Steamboat Willie.” Will there be an iconic character created in 2020 that rivals the impact Mickey has had on children? (Baby Yoda anyone?)

Sliced bread was produced commercially in 1928 in Chillicothe, MO. Will we see something in the 2020s that will actually be the best thing since sliced bread??

Three Year Reflection and 2023 Thoughts:

How quickly characters go out of style.  I thought Baby Yoda would stick around for a while, but only remembered him when reading this article.  Iconic characters in these days seem to be those that are either in binge-worthy series (Eleven and Eddie, Wednesday Adams, Tiger King) and/or political/sports icons/social media influencers (Messi, Trump, Musk, The Kardashians, Mr. Beat, Jake Paul) instead of actual characters.

As for the next sliced bread, many would say that blockchain and crypto could have been it.  While blockchain technologies have applications and are being used in some areas of insurance, they haven’t gotten the adoption that was hoped for (yet).  With crypto, the FTX fallout and price of Bitcoin freefalling don’t help the sector.  There are new AI tools like Chat GPT and AI Time Machine that have come into play and created some fun posts during the holiday season.

Regardless, and as mentioned above under Trend #5, I feel that there will be more continued investment in insurtechs enabling incumbents and agents rather than those competing with them.  Many commentators have spoken about insurtechs being the ‘Digital Insurers of the Future’, but the successful adoption of digital tech by incumbents signals that every successful insurer in the future will be digital.  insurtechs can continue to enable the transition from analog to digital by selling their solutions to incumbents (as we’ve seen with some of the original D2C insurtechs).  With the 1920’s being labeled ‘The Roaring 20s’ in the US, perhaps the incumbents will be ‘roaring’ their way into digital excellence, where every insurer becomes a digital insurer

Lastly, and not covered in my 2020 article are the trends around Digital Health.  In the ‘1920s when healthcare professionals started using medical records to document details, complications, and outcomes of patient care. In 1928, the American College of Surgeons (ACOS) established the Association of Record Librarians of North America (ARLNA) – now known as the American Health Information Management Association (AHIMA) – to standardize medical records’.4 On the Life and Health insurance side in the US, many companies, including RGA, Human API, MIB, Clareto and others have been tapping into Electronic Health Record (EHR) data for underwriting, prevention, and claims.  The pandemic has brought on more acceptance for Digital Health related tools and I expect to see more tools and adoption as we continue to go forth into this decade.

I’d love to hear your thoughts and what trends you think are coming in the remainder of this decade!






Headline image sources:


About Stephen Goldstein

Stephen Goldstein is a multi-disciplined, global insurance executive with experience working on three continents and eight countries. He has held roles in direct sales, sales management, market entry, risk management, advising and investing in startups and reinsurance. Stephen currently serves as an Advisor for two insurtechs, ProNavigator and Finaeo, and consults with insurance carriers and insurtechs on growing revenue, launching go to market initiatives and accelerating innovation adoption.

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