As I reflect on our first two Vanguards pitch competitions of 2026, it’s easy to see why InsurPitch is gaining so much traction—and why our events in Dublin, Ireland, and Sydney, Australia, saw triple the entries and double the attendance compared to their 2024 debuts.

InsurPitch enters its fifth year with a return to Dublin, Ireland on May 21 

More innovators are focusing AI and other technologies on serious pressure points. Unstructured information is becoming decision-ready intelligence. Distribution is moving where customers already do business. Intervention is shifting upstream, before problems become costly crises. And more senior carrier leaders are looking for credible partners capable of helping them solve challenges and seize opportunities too urgent to wait their turn on a multiyear transformation roadmap.

Meanwhile, previous winners are showing how quickly five minutes of visibility can become something larger.

“InsurPitch is a stepping stone into the Guidewire ecosystem and really enables you to get visibility of your solution to Guidewire’s global customer base,” said Michael Flanagan, founder and CEO of 2024 InsurPitch Dublin winner Xtract. “Nothing builds credibility faster than a joint customer telling Guidewire why they chose you. That’s a proof point that really opens doors.”

Momentum is the message. It says regional insurtech sectors are deepening, carrier demand is intensifying, and the distance between a persistent challenge and a focused solution is shrinking fast.

A Competition Worth Six Points of Combined Ratio

As margins tighten, regulatory mandates proliferate, and AI reshapes virtually every aspect of P&C and general insurance worldwide, insurtech is moving from the industry’s periphery toward the center of carrier strategies—and the case is compelling.

Carriers leading in the use of technologies like AI and advanced analytics, for example, achieve combined ratios 6% lower and premium growth 3% higher than their less tech-savvy rivals. According to McKinsey, they also deliver 6.1 times the five-year total shareholder returns.

To be successful, carriers must wield these and other technologies to simultaneously transform unstructured information into actionable intelligence, preserve institutional expertise, identify risks earlier, improve customer experiences, and make complex decisions faster and more consistently. It’s a mandate that’s outpacing any carrier’s ability to build every required capability on their own.

It’s the primary driver behind global P&C insurtech funding, which hit $3.49 billion in 2025, before topping $1.6 billion in Q1 2026—35% more than a year earlier and the strongest first quarter since 2022. AI-focused companies continue to attract the lion’s share of funding. These trends are also propelling the growth of our InsurPitch competition and the incubator program behind it.

InsurPitch: Countdown to the Cutting Edge

Guidewire’s Insurtech Vanguards incubator program identifies compelling new insurtech value propositions and introduces them to our global carrier community as we scout for potential additions to our industry-leading partner ecosystem. In 2022, six members of the incubator were promoted to Guidewire’s PartnerConnect program. In fiscal year 2026, the program’s roster of successful promotions has grown to 26.

Now in their fifth year, our InsurPitch competitions play a key role in all of this by bringing the Insurtech Vanguards mission onstage. In each regional showdown, five finalists selected by Guidewire from ever-growing pools of entrants make live, five-minute pitches to packed audiences of insurance industry professionals.

For insurtechs, the competitions create unprecedented visibility, feedback, and potential pathways into the PartnerConnect program. In fact, our 2024 InsurPitch champions in Dublin (Xtract) and Sydney (Codafication) have both graduated to become full-fledged Guidewire partners. InsurPitch Toronto 2025 winner ProNavigator was acquired outright by Guidewire soon after its victory.

For carriers, the competition series offers a firsthand look at modular innovations that can help them improve profitability, reduce claims friction, enhance customer experiences, and accelerate the return on technology investments. Our 2026 events in Dublin and in Sydney brought this appeal to vivid life.

InsurPitch Dublin: Doubling Down on Innovation

Let’s start with InsurPitch Dublin on May 21. More than 170 attendees—including representatives from 19 carriers—gathered at Sandbox VR to watch pitches from five finalists chosen from a competition that included 20 of the region’s most innovative early-stage insurtechs.

Carriers connect with cutting-edge insurtechs like Inaza during 2026’s first InsurPitch event

With AI-based solutions addressing challenges spanning distribution, underwriting, claims, customer engagement, and litigation, our finalists befit a region that has become an epicenter for insurtech innovation with disproportionate global reach. Ireland is the EU’s fourth-largest insurance hub, where operations centers for Aviva, AIG, Zurich, and others are making significant investments in insurtech. Indeed, Ireland is home to more than 120 insurtechs operating across 17 countries.

Blink Parametric takes the stage during InsurPitch Dublin 2026’s live pitch presentations

Our InsurPitch Dublin finalists included:

Blink Parametric

Embedded, real-time travel and cyber digital assistance to consumers.

Inaza

AI automation for underwriting, claims, customer service, and operations.

Kayna

Infrastructure for embedding commercial insurance into vertical SaaS.

Miss Moneypenny Technologies

Turns digital wallets into embedded distribution and servicing channels.

SettleIndex

Predictive modeling to resolve injury and general claims quickly and fairly.

An InsurPitch First: Two Winners

For the first time in InsurPitch history, judges from companies like Stripe and insurers like EverestRe Ireland and FBD Insurance, supported by attendee votes, selected two Grand Prize winners:

Kayna and Miss Moneypenny  

In a first-ever tie, Kayna and Miss Moneypenny Technologies take top honors at InsurPitch Dublin 2026 

Sydney: Earlier Is the Edge

Fast-forward 76 days and 10,693 miles to the southeast. On August 5, 185 attendees from 18 carriers arrived at The Mint in Sydney to explore how AI and other technologies can help them avoid compliance failures, untreated psychological risks, underinsurance, policy ambiguity, and fragmented property claims.

Industry leaders gather as InsurPitch Sydney 2026 gets underway on August 5

Collectively, the entrants showcased the importance of upstream intelligence and shined a light on some of the most prevalent pressure points in the ANZ region. In Australia, for instance, mental health conditions now account for 12% of serious workers’ compensation claims, with median time lost reaching 35.7 weeks and compensation hitting $67,400.

Five Australian insurtech competitors took the stage, each applying AI to confront a different carrier challenge, but all sharing a common proposition: The earlier insurers can see what’s developing, the greater their opportunity to change what happens next. Our finalists included:

Curium 

Real-time, AI-based compliance intelligence for complex insurance markets.

Haven ERM

Confidential employee disclosure management for proactive prevention and compliance.

myVal

Digital contents capture, valuation, and documentation for faster, fairer homeowners’ claims.

Raindrop

Leverages AI to transform complex policy documentation into structured insurance intelligence.

Sync Technologies

Visual AI-based property intelligence for streamlining building insurance decisions.

myVal vies for the chance to be showcased at Guidewire Connections 2026

A Vision for the Future of Insurance

Supported by attendee votes, judges from organizations like Achmea Australia, IAG, Hollard, and others selected a Grand Prize winner:

Sync Technologies

Sync Technologies wins Grand Prize at the 2026 Guidewire Insurtech Vanguards pitch event in Sydney

Next Stop: Las Vegas

The 2026 InsurPitch season continues September 30 in Las Vegas during ITC. If Dublin and Sydney are any indication, the next five finalists won’t merely show us what emerging insurtech innovation can do. They’ll show us which P&C problems and opportunities just met their match.

My heartfelt thanks to every Dublin and Sydney entrant and finalist; our judges; Imran Ilyas and PwC for sponsoring these competitions; and everyone helping to turn five-minute pitches into meaningful P&C progress.

For more on Guidewire’s first two InsurPitch competitions of 2026, watch the short video postcards below: