REFLECTION AND DISCUSSION
FEBRUARY 22, 2026 - Thanks to Asymmetrix for sending over an updated Flood Risk Data Providers market map.
A couple of weeks ago I posted how their published list went from 21 to 30 in a matter of a few days once providers commented on their original post. 2 weeks later the list now stands at 36.
This is just one example of how crowded the InsurTech space is. If you’re an insurance provider looking to make use of these new services, how do you navigate through all the white noise? If you’re an InsurTech providing new innovative data and technology solutions, how do you differentiate yourself and satisfy your investors?
In crowded spaces, relationships matter more than ever.
View on LinkedIn.
A couple of weeks ago I posted how their published list went from 21 to 30 in a matter of a few days once providers commented on their original post. 2 weeks later the list now stands at 36.
This is just one example of how crowded the InsurTech space is. If you’re an insurance provider looking to make use of these new services, how do you navigate through all the white noise? If you’re an InsurTech providing new innovative data and technology solutions, how do you differentiate yourself and satisfy your investors?
In crowded spaces, relationships matter more than ever.
View on LinkedIn.
FEBRUARY 4, 2026 - I've worked in the insurance industry for more than 3 decades starting as a young actuary for a national industry association. Whenever we thought we had seen everything there was to see, something new always came along. It’s what kept the industry interesting. In recent years, hot topics have been around cyber, climate change, driverless cars, ride-share programs, short-term rentals, and so on.
We’re now in the world of InsurTech, where new players emerge so fast, it’s hard to keep track. As an example, Asymmetrix recently produced the graphics below. Within a few days of posting the first one, “missing” players commented on the post, and a new graphic came out. The number of identified players in the “Flood Risk Data Providers” space went from 21 to 30 in a matter of a few days.
Whether you’re in this specific InsurTech space or another one, the question is how do you differentiate yourself? That’s when relationships matter.
Spaces are getting crowded and relationships matter more than ever, and you’ll need more than AI to get your message out. Otherwise, you're just part of the white noise.
View on LinkedIn.
We’re now in the world of InsurTech, where new players emerge so fast, it’s hard to keep track. As an example, Asymmetrix recently produced the graphics below. Within a few days of posting the first one, “missing” players commented on the post, and a new graphic came out. The number of identified players in the “Flood Risk Data Providers” space went from 21 to 30 in a matter of a few days.
Whether you’re in this specific InsurTech space or another one, the question is how do you differentiate yourself? That’s when relationships matter.
Spaces are getting crowded and relationships matter more than ever, and you’ll need more than AI to get your message out. Otherwise, you're just part of the white noise.
View on LinkedIn.
FEBRUARY 3, 2026 - Relationships and critical thinking are more important than ever.
Don’t be part of the white noise. If you’re an InsurTech trying to get your message out, you know you’re in a crowded space that’s getting more congested every day. You may have the best solution in the market, but getting your message out to potential clients requires strong relationships with people that will be willing to listen to you and trust your opinions. Otherwise, you’re just white noise.
Mind the gap. If you’re an organization looking to implement an AI Assistant, whether for claims, underwriting, marketing or pricing, you need to ensure you select the solutions that will promote critical thinking within your team and not replace it. Your leaders of tomorrow are in the trenches today and you need to give them the tools that will help them grow into those leaders. Otherwise, you’ll end up with a gap in critical thinking.
When industry leaders made their predictions for 2026, they were correct that 1) this is the year AI moves from experimentation to implementation, but also, and maybe even more important 2) critical thinking and human judgement will be more important than ever.
View on LinkedIn.
Don’t be part of the white noise. If you’re an InsurTech trying to get your message out, you know you’re in a crowded space that’s getting more congested every day. You may have the best solution in the market, but getting your message out to potential clients requires strong relationships with people that will be willing to listen to you and trust your opinions. Otherwise, you’re just white noise.
Mind the gap. If you’re an organization looking to implement an AI Assistant, whether for claims, underwriting, marketing or pricing, you need to ensure you select the solutions that will promote critical thinking within your team and not replace it. Your leaders of tomorrow are in the trenches today and you need to give them the tools that will help them grow into those leaders. Otherwise, you’ll end up with a gap in critical thinking.
When industry leaders made their predictions for 2026, they were correct that 1) this is the year AI moves from experimentation to implementation, but also, and maybe even more important 2) critical thinking and human judgement will be more important than ever.
View on LinkedIn.
JANUARY 26, 2026 - You likely see hundreds of posts regularly coming across talking about topics like “When to use AI tools”, “Gen AI basics”, “Learn how to build AI Agents”, “AI skills to learn”, “Chat GPT Cheat Sheets”, etc.
There’s no lack of information making its way around but is this the information you need to help you select the solution that’s right for you.
Industry leaders recently provided their outlook for 2026. Across the board, the top 2 priorities were that AI will be moving from experimentation to integration, and the critical importance of human judgement despite automation.
You should be looking to achieve both objectives with the solution(s) you choose to move forward with. Not only should you look to achieve more automation, but your new AI Assistant (Assistant) should be working with your team members to ensure that second priority - continuity of critical human judgement. Not only for the short term, but also the long term.
Through demos with various insurance organizations, I’ve seen and heard first-hand the value the right solution can add.
Operational Value & Accuracy: “The way the Assistant processes clinical notes and records is amazing. The way it summarizes everything is a huge need for us.”
Capacity & Hiring Impact: “The Assistant removes a significant portion of the workload from our adjusters while dramatically increasing their overall capacity.”
Strategic Fit & Adoption: “The Assistant achieves a rare balance between AI and human expertise—accelerating our work without diminishing critical judgment. The Assistant really helps with cross-training. We have high performers who want to move into other areas, and this helps to support that.”
The AI solution that’s right for you can also be a valuable hiring and training tool, as the next generation of insurance professionals will be prioritizing organizations that can equip them with the right Assistant(s) so they can grow and become the leaders of tomorrow.
I’ve seen first-hand how this can be accomplished. If you’d like to chat more about this or schedule a demo so you can see it for yourself or discuss how you could participate in one of our Advisory Groups, please reach out.
View on LinkedIn.
There’s no lack of information making its way around but is this the information you need to help you select the solution that’s right for you.
Industry leaders recently provided their outlook for 2026. Across the board, the top 2 priorities were that AI will be moving from experimentation to integration, and the critical importance of human judgement despite automation.
You should be looking to achieve both objectives with the solution(s) you choose to move forward with. Not only should you look to achieve more automation, but your new AI Assistant (Assistant) should be working with your team members to ensure that second priority - continuity of critical human judgement. Not only for the short term, but also the long term.
Through demos with various insurance organizations, I’ve seen and heard first-hand the value the right solution can add.
Operational Value & Accuracy: “The way the Assistant processes clinical notes and records is amazing. The way it summarizes everything is a huge need for us.”
Capacity & Hiring Impact: “The Assistant removes a significant portion of the workload from our adjusters while dramatically increasing their overall capacity.”
Strategic Fit & Adoption: “The Assistant achieves a rare balance between AI and human expertise—accelerating our work without diminishing critical judgment. The Assistant really helps with cross-training. We have high performers who want to move into other areas, and this helps to support that.”
The AI solution that’s right for you can also be a valuable hiring and training tool, as the next generation of insurance professionals will be prioritizing organizations that can equip them with the right Assistant(s) so they can grow and become the leaders of tomorrow.
I’ve seen first-hand how this can be accomplished. If you’d like to chat more about this or schedule a demo so you can see it for yourself or discuss how you could participate in one of our Advisory Groups, please reach out.
View on LinkedIn.
JANUARY 25, 2026 - For those who have followed some of my posts or viewed my Insights newsletter on my website, you’ll know I created the diagram below a few months ago to promote the importance of data confidence. We've all learned early on that if A=B and B=C then A=C. https://lnkd.in/gChF9umJ
But the issue is that sometimes data elements and metrics like "B" are defined and interpreted differently thus creating a situation where A is not equal to C, and chaos ensues.
When starting this discussion a few months ago, I was purely thinking of this concept from a business standpoint avoiding frustration, concerns and skepticism in using your data.
But from some of the events of recent weeks, you can see this can also apply to everyday life when the red bin interpretes "B" differently than the blue bin.
The result is A ≠ C. So, frustration, concerns and skepticism, or rather chaos ensues.
View on LinkedIn.
But the issue is that sometimes data elements and metrics like "B" are defined and interpreted differently thus creating a situation where A is not equal to C, and chaos ensues.
When starting this discussion a few months ago, I was purely thinking of this concept from a business standpoint avoiding frustration, concerns and skepticism in using your data.
But from some of the events of recent weeks, you can see this can also apply to everyday life when the red bin interpretes "B" differently than the blue bin.
The result is A ≠ C. So, frustration, concerns and skepticism, or rather chaos ensues.
View on LinkedIn.
JANUARY 19, 2026 - Canada has had more than one “whisky war” in the last few years.
More recently, in 2025, it involved taking U.S. Bourbon off the shelves in Canadian liquor stores because of tariffs.
But before that, there was a more peaceful ending to another one with Denmark over the tiny Hans Island.
True story. Excerpt from a story by the Canadian Press (June 14, 2022):
[Canadian Foreign Affairs Minister Melanie] Joly hailed the signing as a “historic day,” adding that it ended the “friendliest of all wars” which involved both nations leaving bottles of spirits on the island with little notes for one another while removing each other’s flags.
After the signing of the deal, the foreign ministers symbolically exchanged bottles of spirits, with notes attached, to end the “whisky war.”
View on LinkedIn.
More recently, in 2025, it involved taking U.S. Bourbon off the shelves in Canadian liquor stores because of tariffs.
But before that, there was a more peaceful ending to another one with Denmark over the tiny Hans Island.
True story. Excerpt from a story by the Canadian Press (June 14, 2022):
[Canadian Foreign Affairs Minister Melanie] Joly hailed the signing as a “historic day,” adding that it ended the “friendliest of all wars” which involved both nations leaving bottles of spirits on the island with little notes for one another while removing each other’s flags.
After the signing of the deal, the foreign ministers symbolically exchanged bottles of spirits, with notes attached, to end the “whisky war.”
View on LinkedIn.
JANUARY 14, 2026 - Let’s create a story. An InsurTech journey seems to follow pretty closely the tracks of Pink Floyds’ classic 1973 The Dark Side of the Moon.
Track 1 - “Speak to Me” – An idea came to me for a new product.
Track 2 - “Breathe (In the Air)” – Let’s do research and gather the information.
Track 3 - “On the Run” – We have enough to get started. Let’s run with it.
Track 4 - “Time” – This is going to take a lot more time than we thought.
Track 5 - “The Great Gig in the Sky” – This will be great. Everyone will want it.
Track 6 - “Money” – We need more capital, another round of funding.
Track 7 - “Us and Them” – Looks like we have competition.
Track 8 - “Any Colour You Like” – We can customize. That’s our advantage.
Track 9 - “Brain Damage” – This is not easy. I’m getting burnt out.
Track 10 - “Eclipse” – Everything is going dark. Wait, the Sun’s coming out!
It’s always fun to create stories. In this case it's like putting an idea through a prism and seeing all the colours come out on the other side. I wonder if this is what Pink Floyd was thinking in 1973.
View on LinkedIn.
Track 1 - “Speak to Me” – An idea came to me for a new product.
Track 2 - “Breathe (In the Air)” – Let’s do research and gather the information.
Track 3 - “On the Run” – We have enough to get started. Let’s run with it.
Track 4 - “Time” – This is going to take a lot more time than we thought.
Track 5 - “The Great Gig in the Sky” – This will be great. Everyone will want it.
Track 6 - “Money” – We need more capital, another round of funding.
Track 7 - “Us and Them” – Looks like we have competition.
Track 8 - “Any Colour You Like” – We can customize. That’s our advantage.
Track 9 - “Brain Damage” – This is not easy. I’m getting burnt out.
Track 10 - “Eclipse” – Everything is going dark. Wait, the Sun’s coming out!
It’s always fun to create stories. In this case it's like putting an idea through a prism and seeing all the colours come out on the other side. I wonder if this is what Pink Floyd was thinking in 1973.
View on LinkedIn.
JANUARY 11, 2026 - Mind the gap.
The 2026 outlook from industry leaders put a lot of emphasis on AI moving from experimentation to integration, followed by the critical importance of human judgement despite automation.
Considering the insurance claims process, as an example, the continuity of critical human judgement could easily get overlooked. In the short term, with competitive pressures, the automation piece will get done to use the technology to reduce the administrative burden of reviewing and summarizing medical records, diaries, legal and other documents, while also providing new insights and allowing senior leaders to focus on the more complex files. The process of integrating AI technology with the right questions, or prompts, will be a reiterative one, but it will continue to progress.
Also in the short term, experienced resources to handle the oversight and management of complex files in addition to the overall Claims operations will be available. These resources have gone through the learning curve to make them leaders in their field, having gone through the traditional steps of learning on the job.
But as the technology evolves and takes over many of the “learn on the job” tasks, if there’s a reduced need for junior resources, years from now, where will the experienced resources come from? This is where the continuity gap of human judgement could start appearing if not addressed.
In addition to the desired improvements in efficiencies automation will bring, your new AI “assistant” should also be able to work in tandem with your team members, so they can develop into the senior leaders of tomorrow and maintain that valuable human judgement continuity.
When selecting your AI-enabled solutions, “Mind the gap”.
View on LinkedIn or learn more about your new Claims Assistant by visiting Sky AI.
The 2026 outlook from industry leaders put a lot of emphasis on AI moving from experimentation to integration, followed by the critical importance of human judgement despite automation.
Considering the insurance claims process, as an example, the continuity of critical human judgement could easily get overlooked. In the short term, with competitive pressures, the automation piece will get done to use the technology to reduce the administrative burden of reviewing and summarizing medical records, diaries, legal and other documents, while also providing new insights and allowing senior leaders to focus on the more complex files. The process of integrating AI technology with the right questions, or prompts, will be a reiterative one, but it will continue to progress.
Also in the short term, experienced resources to handle the oversight and management of complex files in addition to the overall Claims operations will be available. These resources have gone through the learning curve to make them leaders in their field, having gone through the traditional steps of learning on the job.
But as the technology evolves and takes over many of the “learn on the job” tasks, if there’s a reduced need for junior resources, years from now, where will the experienced resources come from? This is where the continuity gap of human judgement could start appearing if not addressed.
In addition to the desired improvements in efficiencies automation will bring, your new AI “assistant” should also be able to work in tandem with your team members, so they can develop into the senior leaders of tomorrow and maintain that valuable human judgement continuity.
When selecting your AI-enabled solutions, “Mind the gap”.
View on LinkedIn or learn more about your new Claims Assistant by visiting Sky AI.
JANUARY 9, 2026 - “A society grows great when old men plant trees, the shade of which they know they will never sit in.”
I recently heard this quote and thought of the impact AI will be having on the insurance industry, specifically in the Claims area.
When you ask insurance leaders about their outlook for 2026, the list usually starts with 1) this will be the year when AI moves from experimentation to integration, and 2) human judgement will remain critical despite automation.
Claims are typically document-intensive, but never more than when handling Accident Benefits (AB) and Liability claims, with reviews of medical records, diaries and legal records. The ever-evolving auto insurance product always presents challenges and new regulations and standards to abide by. And more changes are coming to the Ontario and Alberta products over the next year, posing new challenges.
IT’S TIME TO BRING IN A NEW CLAIMS ASSISTANT (CA)
The claims handling process will see a shift in the coming years, with a new CA to help alleviate some of the administrative burden of these tasks, allowing the more experienced adjusters and claims leaders to focus on the type of files that require more judgement.
The new CA will provide immediate benefits and relief from much of the administrative burden and be able to provide new insights, but you will always need senior claims professionals to provide that valuable human judgement on the more complex files. Remember, however, that these experienced professionals were once juniors. The CA shouldn’t eliminate the junior claims handlers, but rather, they should be working together.
If you’d like to see an AI Claims Assistant in action, please reach out and we can discuss further. We have a solution that's ready today.
Think of your claims team as a society.
View on LinkedIn or learn more about your new Claims Assistant by visiting Sky AI.
I recently heard this quote and thought of the impact AI will be having on the insurance industry, specifically in the Claims area.
When you ask insurance leaders about their outlook for 2026, the list usually starts with 1) this will be the year when AI moves from experimentation to integration, and 2) human judgement will remain critical despite automation.
Claims are typically document-intensive, but never more than when handling Accident Benefits (AB) and Liability claims, with reviews of medical records, diaries and legal records. The ever-evolving auto insurance product always presents challenges and new regulations and standards to abide by. And more changes are coming to the Ontario and Alberta products over the next year, posing new challenges.
IT’S TIME TO BRING IN A NEW CLAIMS ASSISTANT (CA)
The claims handling process will see a shift in the coming years, with a new CA to help alleviate some of the administrative burden of these tasks, allowing the more experienced adjusters and claims leaders to focus on the type of files that require more judgement.
The new CA will provide immediate benefits and relief from much of the administrative burden and be able to provide new insights, but you will always need senior claims professionals to provide that valuable human judgement on the more complex files. Remember, however, that these experienced professionals were once juniors. The CA shouldn’t eliminate the junior claims handlers, but rather, they should be working together.
If you’d like to see an AI Claims Assistant in action, please reach out and we can discuss further. We have a solution that's ready today.
Think of your claims team as a society.
View on LinkedIn or learn more about your new Claims Assistant by visiting Sky AI.
JANUARY 2, 2026 - Will AI have a Y2K moment? First, a bit of history.
The computer first arrived in the 1940s with wide mainframe usage in the 60s and 70s to handle large-scale data processing. The world was just learning how to use this new shiny toy. But to use these big machines, programming languages were created, and the computer became essential for business and government.
Throughout the 60s, 70s and 80s, programs were written and the business world was humming along. But when the 90s rolled around, Y2K reared its ugly head. If you’re old enough, you remember this was a simple issue: to save space, 2-digit years as opposed to 4 digits were used in most computer programs. The world as we knew it was so dependent on the computer, it was going to end if the problem wasn’t fixed before the stroke of midnight on December 31st, 1999.
I remember two thoughts I had at the time.
One. I was impressed that computer programs written in the 60s and 70s were still effective and operational in the late 90s. They weren’t being replaced, but rather they would be updated. At significant costs, no less. Organizations were on the hunt for programmers that still knew how to write code in languages like Assembly and COBAL. Still, it was impressive that these programs continued to be operational decades later.
Two. I was surprised that some of the programs written not so long before, some as recent as in the 80s, didn’t have the vision that a 2-digit year would be an issue in the not-so-distant future. I don’t blame the programmers. Their job was to make the program work and had limited space on the record layout to work with.
Now we turn to a new shiny toy.
Reading about the outlook for 2026 from business leaders, you’ll hear that 2026 is the year AI becomes foundational and moves from experimentation to full-scale deployment. If we fast-forward a decade or two and look back to 2026, what will impress us and what will surprise us about how we handled AI today?
Let’s avoid another Y2K situation, as the next one could prove much more costly. Yes, AI is here to stay but let’s do it right. Let’s not miss something as simple as a 4-digit year.
View on LinkedIn.
The computer first arrived in the 1940s with wide mainframe usage in the 60s and 70s to handle large-scale data processing. The world was just learning how to use this new shiny toy. But to use these big machines, programming languages were created, and the computer became essential for business and government.
Throughout the 60s, 70s and 80s, programs were written and the business world was humming along. But when the 90s rolled around, Y2K reared its ugly head. If you’re old enough, you remember this was a simple issue: to save space, 2-digit years as opposed to 4 digits were used in most computer programs. The world as we knew it was so dependent on the computer, it was going to end if the problem wasn’t fixed before the stroke of midnight on December 31st, 1999.
I remember two thoughts I had at the time.
One. I was impressed that computer programs written in the 60s and 70s were still effective and operational in the late 90s. They weren’t being replaced, but rather they would be updated. At significant costs, no less. Organizations were on the hunt for programmers that still knew how to write code in languages like Assembly and COBAL. Still, it was impressive that these programs continued to be operational decades later.
Two. I was surprised that some of the programs written not so long before, some as recent as in the 80s, didn’t have the vision that a 2-digit year would be an issue in the not-so-distant future. I don’t blame the programmers. Their job was to make the program work and had limited space on the record layout to work with.
Now we turn to a new shiny toy.
Reading about the outlook for 2026 from business leaders, you’ll hear that 2026 is the year AI becomes foundational and moves from experimentation to full-scale deployment. If we fast-forward a decade or two and look back to 2026, what will impress us and what will surprise us about how we handled AI today?
Let’s avoid another Y2K situation, as the next one could prove much more costly. Yes, AI is here to stay but let’s do it right. Let’s not miss something as simple as a 4-digit year.
View on LinkedIn.
DECEMBER 30, 2025 - As we welcome 2026, this will also mark the 150th anniversary of when Alexander Graham Bell first patented the telephone. A lot has been invented since the phone first appeared on the scene but there was always one constant before then.
Long before “Planes, Trains and Automobiles” the horse was the main source of overland transportation.
Long before telegraphs, phones and the internet, the horse was the fastest way to deliver news and information.
Long before computers and AI, the horse was your most reliable work assistant whether you were working the land or transporting goods.
The main difference between all those innovations and the horse, is they were all man-made. Is there another horse out there? Something we didn't invent that we couldn't do without in everyday life.
Think back a few centuries and try to imagine a world without horses.
Happy New Year everyone!
View on LinkedIn or see REAL INSIGHTS page for this and more stories.
Long before “Planes, Trains and Automobiles” the horse was the main source of overland transportation.
Long before telegraphs, phones and the internet, the horse was the fastest way to deliver news and information.
Long before computers and AI, the horse was your most reliable work assistant whether you were working the land or transporting goods.
The main difference between all those innovations and the horse, is they were all man-made. Is there another horse out there? Something we didn't invent that we couldn't do without in everyday life.
Think back a few centuries and try to imagine a world without horses.
Happy New Year everyone!
View on LinkedIn or see REAL INSIGHTS page for this and more stories.
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