AI Is Key: What 35 Canadian Insurance Leaders Revealed About 2026

A roundup of Canadian Underwriter's 2026 Executive Outlook series—where 80% of industry leaders say AI moves from pilot projects to operational reality this year

Between December 2025 and early January 2026, Canadian Underwriter published its annual Executive Outlook series—35 perspectives from thought-leaders across Canada's property and casualty insurance industry, plus an overview article setting the stage. The question posed was straightforward: What's the biggest change coming in 2026?

The answers revealed an overwhelming consensus.

After the SortSpoke team analyzed all 35 executive outlooks—featuring leaders from major carriers like Intact Financial and Aviva Canada, national brokerages including HUB International and BFL Canada, global advisory firms such as Aon and Marsh, reinsurers like Swiss Re, and industry organizations like the Insurance Bureau of Canada—a clear pattern emerged:

80% identified artificial intelligence as a key priority for 2026, with nearly half naming it their top focus.

But, this isn't about AI experimentation anymore. It's about implementation. For leaders like you navigating 2026, the message is clear: the time for pilots without a plan to implement has passed.

"The experimentation stage is now over. Things will start to get real in 2026."

— David Gambrill, Senior Editor, Canadian Underwriter

David Gambrill, Canadian Underwriter's Senior Editor, set the tone in his series overview. That prediction played out across nearly every article that followed. From underwriting VPs to broker CEOs, from reinsurance executives to fraud investigators, the message was consistent: 2026 marks the year AI transitions from pilot projects to operational reality.

This roundup highlights the key themes from across the series—distilling 35 executive perspectives into actionable insights about what's changing, what's at stake, and what separates leaders from laggards as the industry enters this implementation phase.

To help you benchmark your team's readiness, we have included a few supplemental resources below, including our 2026 Industry Outlook Infographic and a full breakdown of all the outlook articles.

We hope you find these insights helpful as you navigate the year ahead!

From Pilot to Production: What Implementation Looks Like

Across Canadian Underwriter's outlook series, the language these thought-leaders used marked a clear evolution. Where 2025 discussions centered on "exploring" and "testing," the 2026 perspectives focused on "deploying," "scaling," and "integrating."

The Language Shift: 2025 → 2026

"When it comes to the application of AI, what we'll see in 2026 will be fundamentally different than what came before. 2026 will be the year insurers move from experimenting with AI to realizing its full potential."

— Laura Doddington, WTW

With the quote of the year Laura Doddington of WTW captured this shift perfectly in her outlook article. The shift isn't just rhetorical—it's operational. And for leaders like you, it signals a clear imperative.

What Canadian Insurance Leaders Are Focused On

Here's how the 35 executives broke down by primary focus area:

AI Applications Highlighted Across the Series

Across the 35 outlooks, executives identified AI applications touching every aspect of operations:

AI In Underwriting

Swiss Re's Jolee Crosby highlighted how "AI is becoming increasingly embedded across the risk value chain," particularly for assessing secondary perils—wildfire, hail, and flood risks—that traditional methods struggled to model accurately. Read her full perspective.

For carriers looking to implement AI in their underwriting workflows, the challenge isn't just the technology—it's the data. Automated document processing for submissions is enabling underwriters to extract structured data from complex documents faster, freeing them to focus on actual risk assessment rather than manual data entry.

AI In Claims Processing

Multiple executives in the series pointed to proactive claims management as AI's breakthrough application. Desjardins' Valerie Lavoie described an industry "moving from a reactive model to a proactive one, where insurers help build stronger communities" through AI-enabled prediction and prevention. Read more.

AI In Distribution

"Consumers are no longer passive recipients of quotes. They are active digital shoppers, using AI-powered platforms to find tailored coverage, compare rates in real-time and receive instant recommendations."

— Grant Ostir, Western Financial Group

Grant Ostir of Western Financial Group observed how consumer behavior is fundamentally changing as AI-powered platforms reshape how Canadians shop for insurance.

2026 In Fraud Detection

Équité Association's Terri O'Brien highlighted AI's capability to uncover patterns across massive datasets, though she cautioned that "criminals are making AI their full-time job" too—creating an ongoing arms race. Read her perspective.

The Business Case Cited Throughout

Several outlook articles pointed to concrete pressures driving this urgency. Canada recorded $8.9 billion in catastrophe losses in 2024. Market dynamics are diverging—commercial insurance softening while personal lines remain hard. In this environment, multiple executives positioned AI not as a luxury but as a competitive necessity.

"If this was the year when the property and casualty insurance industry embraced AI, 2026 will be the year it transforms because of it."

— Rob Rasberry, NFP Canada

As NFP Canada's Rob Rasberry put it, transformation isn't coming—it's already here.

The Speed vs. Security Dilemma

While the Canadian Underwriter series revealed widespread enthusiasm for AI implementation, several executives raised critical concerns about rushing deployment without adequate safeguards.

"The pressing question for the industry next year is whether speed or security will prevail in the AI race."

— Alex Barker, AXA XL

Alex Barker of AXA XL framed the tension clearly in his outlook article. As organizations rush to deploy AI, interconnected systems create multiple potential failure points requiring organizations to "understand and mitigate new cyber risks."

The Cybersecurity Challenge

Multiple outlook articles flagged cybersecurity as a primary concern. The threat is evolving in parallel with adoption. Mitch Insurance's Adam Mitchell predicted that "AI will take cybercrime to unprecedented levels in 2026. Both the volume and sophistication of text, voice and video deepfakes are already making it harder to spot scams." Read his full analysis.

The deepfake threat isn't theoretical—it's already impacting claims verification and customer authentication processes across the industry.

The Governance Gap

Beyond technical security, the series highlighted governance challenges. Allianz Commercial's Bernard McNulty emphasized that "the risks associated with AI use need to be identified and managed," noting that risks related to "reputation, culture and role displacement" may prove harder to address than technical failures. Read more.

"Contracts with third-party AI partners will need to be carefully crafted, bearing in mind regulators will hold the broker accountable for outcomes."

— Philomena Comerford, Baird MacGregor

Brokers face particular pressure, as Philomena Comerford of Baird MacGregor noted in her outlook. The regulatory accountability for AI-driven decisions remains squarely on the brokerage, regardless of which third-party tools they deploy.

The Human Factor: A Recurring Theme

One of the most consistent threads across Canadian Underwriter's outlook series was the focus on people. Eight executives explicitly identified talent and workforce transformation as critical to 2026 success—and their message may surprise those fearing wholesale automation.

"In insurance, we trade on trust; the reputations of individuals and organizations matter. Success in 2026 will be defined by our ability to deliver streamlined digital experiences without compromising the expert advice, judgment, and relationship-building that have long been hallmarks of our industry."

— Richard Grant, Trisura Group Ltd.

Richard Grant of Trisura Group captured this balance perfectly in his perspective. AI makes human expertise more valuable, not less.

The Talent Challenge Across the Series

Multiple outlook articles highlighted Canada's insurance talent crisis. Aviva Canada's Nav Dhillon identified it as "a defining challenge in 2026—a critical talent gap intensified by the rise of artificial intelligence." Read his full outlook.

The challenges are structural: retirements outpacing new entrants, particularly in specialized roles. Meanwhile, Gen Z professionals gravitate toward tech-enabled careers, creating fierce competition for talent that bridges insurance expertise with technological capability.

The Winning Formula From the Series

But several executives across the series pushed back against "AI replaces humans" narratives. BrokerLink's Joe D'Annunzio stated it directly: "AI is a powerful tool that can enhance many aspects of the insurance industry, it won't replace the need for human contact." Read more.

"Those adapting quickly and investing in both technology and people will be best positioned to excel in this new landscape."

— Catherine Roe, President, CNA Canada

CNA Canada President Catherine Roe, in one of the series' most comprehensive outlooks, emphasized that leaders will be "those adapting quickly and investing in both technology and people."

"Market leaders will treat AI and data as accelerants, not substitutes for judgment."

— Rob Marsh, Liberty Mutual Canada

Liberty Mutual Canada's Rob Marsh captured the balance succinctly: "Market leaders will treat AI and data as accelerants, not substitutes for judgment."

This is the key insight: AI doesn't replace underwriter expertise in assessing complex risks. It eliminates the manual work—like extracting data from loss runs or chasing missing information—so underwriters can focus on what actually requires judgment.

"Winning in the AI era means building a future-ready workforce that attracts talent, invests in future leaders, and retains skilled experts."

— Nav Dhillon, Aviva Canada

Climate as Catalyst: A Parallel Theme

If there's one force accelerating AI adoption across the Canadian Underwriter series, it's climate change. Twelve executives identified climate-related catastrophe risk as a primary 2026 concern—and nearly all positioned AI as essential to managing this exposure.

The $8.9 billion in insured catastrophe losses Canada experienced in 2024 featured prominently across the outlook series. Northbridge Insurance's Shari Dodsworth noted that "customers will expect more than coverage. They will seek stability and confidence in our services." Read her outlook.

Meeting that expectation requires moving beyond traditional risk modeling to AI-powered predictive analytics that can assess secondary perils and emerging patterns.

Innovation Beyond Traditional Risk Transfer

Some executives in the series highlighted innovation beyond traditional approaches. Beneva's Christian Fournier advocated for "sustainable claims practices" applying circular economy principles—repair and reuse rather than demolish and replace. Read his perspective.

"2026 offers a critical opportunity to leverage favorable market conditions and strengthen resilience in an era of accelerating change."

— Stephane Lesperance, Aon Canada

Aon Canada's Stephane Lesperance framed climate risk as both challenge and opportunity. Organizations that integrate climate data with AI-powered risk assessment tools can differentiate through more accurate pricing and proactive client partnerships.

Patterns Across the Series: Leaders vs. Laggards

Analyzing the 35 perspectives from Canadian Underwriter's outlook series reveals clear patterns separating organizations positioned to thrive from those at risk of falling behind. Here's a comparison based on the insights:

Leaders in 2026 Will:

1. Move decisively from pilots to production

"Those willing to reimagine how work happens will unlock greater efficiency, stronger client outcomes and the next chapter of innovation."

— Tina Osen, HUB International Canada

As HUB International Canada's Tina Osen noted, waiting for perfect solutions means falling behind. The leaders are deploying now and iterating based on real-world results.

2. Invest in both technology and talent simultaneously

This dual investment theme appeared across multiple outlooks, most explicitly in Catherine Roe's (CNA Canada) perspective. Organizations that treat these as either/or decisions will struggle. Those that invest in both will pull ahead.

3. Build governance frameworks proactively

Several executives emphasized establishing clear AI policies before regulatory mandates force reactive compliance. The governance gap is real, and early movers will avoid the scramble that comes with regulatory enforcement.

4. Leverage scale strategically

"The most important shift in 2026 will be the power of scale."

— Shawn DeSantis, Navacord

Navacord's Shawn DeSantis identified "the power of scale" as 2026's critical shift. Larger organizations can invest more effectively in AI infrastructure, data analytics, and specialized expertise. Several Canadian brokerages will surpass $1 billion in revenue in 2026, creating new competitive dynamics.

5. Maintain the human connection

Despite technological capabilities, multiple executives in the series emphasized that trust remains paramount. As Trisura's Richard Grant reminded readers: insurance fundamentally "trades on trust"—something AI can support but never replace.

Laggards Will:

• Continue treating AI as a future consideration rather than present imperative
• Underinvest in change management and workforce development
• Rush deployment without adequate governance and risk management
• Focus solely on cost reduction rather than value creation
• Neglect the relationship-building that differentiates in commoditized markets

What This Means for You

The themes across Canadian Underwriter's series point to specific actions depending on where you sit in the insurance value chain:

For Carrier Leaders: The shift from experimentation to implementation means moving AI projects out of innovation labs and into production environments. That requires investment in change management, data infrastructure, and workforce training—not just technology procurement.

For Broker Leaders: The message across multiple broker outlooks was clear: AI enables better service, not automated service. The leaders will be those who use technology to handle routine tasks while freeing advisors to focus on complex client needs and relationship building.

For All Insurance Leaders: Whether you're evaluating AI-powered document processing, building internal capabilities, or planning your 2026 technology roadmap, the Canadian Underwriter series makes one thing clear: the time for pilot projects has passed. Implementation is the imperative.

The SortSpoke Perspective

As a company built on AI-powered document processing for insurance, we've had a front-row seat to how carriers, MGAs, and brokers are approaching the AI transition. The executives above aren't just making predictions—they're describing the exact conversations we're having with industry leaders every day.

Three themes stand out to us as we work alongside insurers navigating this shift:

1. Practical AI Beats Perfect AI

The most successful AI implementations we've seen aren't the most ambitious—they're the most practical. Leaders like you don't have time to wait for a "perfect" solution that may never arrive. They need AI that works today, deploys quickly, and delivers measurable ROI within weeks, not years.

The insurers pulling ahead in 2026 are choosing targeted, high-impact use cases—submission intake, document processing, data extraction—rather than boiling the ocean with enterprise-wide transformation projects that stall in committee.

2. No Black Boxes Allowed

Insurance is a regulated industry built on trust and accountability. When an underwriting decision is made, you need to explain why. When a claim is processed, there's an audit trail. AI should be no different.

The thought-leaders in this series repeatedly emphasized governance, transparency, and explainability—and for good reason. Black-box AI that can't show its work isn't just a compliance risk; it's a business risk. Traceable, auditable AI isn't a nice-to-have. It's table stakes.

3. Human-in-the-Loop Is Non-Negotiable

We built SortSpoke around a core belief: AI should augment human judgment, not replace it. The executives in this roundup echo that sentiment. Richard Grant (Trisura) reminds us that "in insurance, we trade on trust." Rob Marsh (Liberty Mutual) emphasizes that AI and data should be "accelerants, not substitutes for judgment."

The leadership formula isn't AI or humans—it's AI and humans, working together. Automation handles the repetitive, time-consuming work. Your people handle the relationships, the judgment calls, and the exceptions that require expertise.

4. Change Management Will Be Your Hardest Job

Here's what often gets underestimated: the technology is the easy part. The hard part is getting your team to embrace it.

Change management—training, communication, workflow redesign, addressing fears about job displacement—will consume more leadership energy than any vendor selection or implementation project.

The executives who called out "talent investment" as a priority understand this. You can buy the best AI in the world, but if your people don't trust it, use it, or understand it, you've bought expensive shelfware.

Prepare for change management to be your most important job in 2026.

"The AI conversation has shifted from 'should we?' to 'how fast can we?' But speed without traceability is a liability. Insurance runs on trust, and trust requires explainability. The carriers leading in 2026 will be the ones who deploy AI that their teams actually use—because they understand it, trust it, and can defend it to regulators and customers alike."

— Jasper Li, CEO, SortSpoke

We're proud to partner with carriers, MGAs, and brokers who are making the leap from experimentation to execution. If you're ready to see what practical, human-in-the-loop AI looks like for document processing, we'd love to show you.

Conclusion: The Series in Summary

Canadian Underwriter's 2026 Executive Outlook series captured an industry at an inflection point. The 35 executive perspectives—from thought-leaders spanning carriers and brokers, regional teams and global firms, established giants and agile specialists—revealed remarkable consensus.

The leaders won't be those with the most sophisticated technology or the largest budgets. For leaders like you, success will come from integrating what the series identified as three critical elements:

Strategic AI deployment delivering tangible business value across underwriting, claims, and distribution

Investment in people building the future-ready workforce capable of leveraging these tools effectively

Robust risk management balancing innovation speed with security, governance, and trust

"Our industry's biggest challenge and biggest opportunity in 2026 stems from the inevitable creep of AI into the daily lives of Canadians. Being there for customers when they need us will keep us relevant."

— Louis Gagnon, Intact Financial Corporation

Intact Financial Corporation's Louis Gagnon perhaps captured it best: AI represents "our industry's biggest challenge and biggest opportunity in 2026."

The question isn't whether transformation is coming—the series makes clear it's already here.

The question is: will your organization lead it, follow it, or fall behind?

The Infographic

Explore the Complete Series

This roundup synthesizes key themes from Canadian Underwriter's 2026 Executive Outlook series. For leaders like you seeking deeper insights, explore all 35 executive perspectives plus the series overview—filtered by your role, line of business, or strategic focus:

Browse the complete 2026 Executive Outlook series →