Sixfold Content

Yesterday, Sixfold hosted an event at Lloyd’s in London on the future of underwriting work.

The event started with a keynote from Dr. Naeema Pasha on the future of work across industries, along with findings from her research with Allianz. One of the key takeaways was that the future of insurance still needs to be focused on people. With AI becoming more present, the question is how to build trust, support empathy and skills development, and design roles for the next generation of talent.

“What stood out in my research with Allianz was how much people in the insurance industry care and are passionate about the industry and its future.“

─ Dr. Naeema Pasha, Researcher, Author and Writer

There was also a great question from an aspiring underwriter asking what skills are needed today. Soft skills came up a lot, things like curiosity and adaptability, but also something simple: get out there, engage with people in the industry, and ask questions.

At one point, the audience was asked if they would let a robot cut their hair. Most people wouldn’t. It’s a simple example, but it comes back to trust.

The panel discussion featured Simon Parris, CUO at Victor Insurance; John Enright, COO at Berkley; and Raoul Carlos, Founder & CEO at Torch Underwriting, and focused on whether this is the last generation of traditional underwriters.

They started by sharing where they are today when it comes to AI implementation. A clear theme was that adoption and engagement from underwriters really matters. Agentic AI is moving fast with a lot of potential, and there was a lot of discussion around how AI can improve broker relationships and risk assessments as a whole. Raoul talked about building AI into their foundation from day one, including the data layer needed to support institutional intelligence over time.

When it came to impact of AI, the conversation went beyond speed. Things like memorable engagement with brokers, pricing power through stronger relationships, more personal service, net promoter score, and the ability to think outside the box all came up. Better service and better products as well.

On hiring the future workforce, Raoul mentioned looking for curiosity and passion. Where the role used to be heavily focused on data wrangling, today it is much more about judgment, adaptability, creativity, and critical thinking. John highlighted integrity, trust, relationship skills, and the ability to work with a new toolkit. Simon mentioned market connections, strong underwriting fundamentals, and openness to new technology.

“The mechanics of how we work are changing, but this has happened hundreds of times throughout history.”

─ Raoul Carlos, Founder & CEO @Torch Underwriting

When asked what the underwriting role of the future might be called, the panel largely agreed it is still underwriting. Portfolio underwriting was mentioned, as well as next generation underwriter, but the core remains the same. From the audience, there were also questions around how to enter the industry. It is not just about academics. Apprenticeships matter. Continuous learning matters. And building teams with different perspectives and backgrounds still really matters.

On dealing with skepticism internally around AI, it was acknowledged that change can be uncomfortable. The advice was to make it part of the conversation, share examples, and host workshops. For insurance executives looking to learn more about AI, the message was to experiment and try it firsthand. Get into vibe coding, step outside of the comfort zone, and understand the opportunities by actually using the tools.

Lastly, Gianfilippo Giannini, Global Technical Coordinator Cyber Risk at Generali GC&C, took the stage for a Q&A and shared why they started looking for an AI vendor in the first place. They were operating in a soft market and needed to handle more submissions with the same headcount.

He also highlighted the importance of bringing underwriters in from the very beginning. The decision to choose Sixfold came down to security, privacy, a strong responsible AI framework, and a future proof roadmap, but also that the solution was clearly built for underwriting.

“Sixfold spoke the same language as us.”
‍
─ Gianfilippo Giannini, Global Technical Coordinator Cyber Risk @Generali GC&C

There was some early skepticism from users, but once underwriters saw how it supported their day to day work, feedback quickly became very positive. At one point, underwriters who were not part of the pilot started asking when they could start using Sixfold as well.

Looking ahead, the focus for Generali GC&C when it comes to AI in underwriting is on data driven underwriting, with better visibility into portfolio trends and broker success rates.

Most insurers have run an AI pilot. Far fewer have scaled one. At a recent Sixfold webinar, two carriers shared what it actually took to get there, and what production at scale really looks like.

Amy Nelsen, Head of UW Operations for US Middle Market at Zurich North America, and Jim Mormile, President of Professional Lines at Skyward Specialty, spoke about their experience rolling out Sixfold across their organizations.

Skyward is now live across more than 10 product lines with nearly 100 underwriters. Zurich has deployed across 30 US offices, with more than 200 underwriters using Sixfold in their daily workflow.

We walked through our five-step scaling framework with both of them to hear, in their own words, how each stage played out in practice.

Step  1: Pick Your Focus

The biggest mistake teams make is starting with AI and working backwards to find a problem. Both Amy and Jim were deliberate about doing the opposite, finding a genuine pain point first and then asking whether AI could solve it.

For Skyward, the problem was the triage wall. Underwriters were spending hours manually working through submissions just to determine basic appetite fit.

For Zurich it was starting with a use case which underwriters didn’t like doing: documentation. 

"We had a healthcare risk where the underwriter got about a 75-page submission. It wasn't until page 56 to 59 that they realized the submission should not be covered since it was out of appetite."
‍
─Jim Mormile @Skyward Specialty

Step 2: Prove It Works

Before scaling, you need a few signals that it's actually working, but that doesn't always come from a dashboard. Both Jim and Amy found that meaningful early indicators were user feedback.

For Jim, it was a veteran underwriter pulling him aside unprompted.

"The anecdotal evidence that really made us realize it was working: it was a veteran underwriter that came up to me and said, '[Sixfold] actually changed my day. It sped up my work progress and workflow'"
‍
─Jim Mormile @Skyward Specialty

The follow-up signal was equally telling “underwriters stopped asking whether they should use Sixfold and started asking when it was coming to their line of business.” That's when Skyward knew it was time to expand.

Step 3: Map Your Expansion

Scaling AI isn't a single rollout but it's a series of decisions about sequencing, readiness, and change management. Both organizations took a structured approach, but in different ways.

Skyward scored each of their 16 lines of business across criteria like guideline robustness, process standardization, underwriting complexity, and, critically, how tech-forward the underwriting team was. They then hand-picked early adopters rather than opening the floodgates.

Zurich took a geographic approach, piloting across four offices before expanding countrywide, and intentionally included underwriters at different levels of tech comfort so they could anticipate resistance before it became a problem at scale.

Both teams also addressed job security fears head-on.

"It's less about the underwriting role becoming irrelevant, and more about if you handle a $10M book of business versus a $20M book of business."
‍
─Amy Nelsen @Zurich North America

Jim's approach was to be explicit about what AI wouldn't do: no automated decision-making, no replacing the underwriter's final judgment. The framing was always about giving underwriters better information, not replacing their expertise.

Step 4: Roll Out in Phases

Both teams learned that trying to do too much too fast creates fatigue, and fatigue kills adoption. Skyward actually hit pause on one line of business after underwriters started showing signs of frustration. Rather than pushing through, leadership made the call to step back.

A few months later, that team came back ready to re-engage, pulled in by the FOMO of watching other lines of business benefit.

On the flip side, Skyward's phased approach led to real efficiency gains in deployment speed. Their first two lines of business took 12 to 14 weeks from introduction to production. By the time they were rolling out subsequent lines, they'd cut that down to eight weeks.

Amy's experience at Zurich echoed the same takeaway on speed:

"The most amazing part is how fast you can get from just a concept to deployment with Sixfold."
‍
─Amy Nelsen @Zurich North America

Step 5: Assess Impact

Once AI is live in production, measuring success means looking at two things in parallel: business outcomes and output quality. Neither alone tells the full story.

For Jim at Skyward, that meant tracking time to quote and number of quotes out the door, but also running a monthly accuracy review and a sentiment score across underwriting teams.

"We constantly look at both ends of the spectrum: the ROI metrics, and whether the accuracy is there to give our underwriters the information they need to make better decisions."
‍
─Jim Mormile @Skyward Specialty

Amy's approach at Zurich was similar, and revealing in its simplicity. Sixfold's success isn't measured separately from the business; it's measured through the business. When AI becomes embedded enough that you stop evaluating it as a standalone tool and start measuring it through your core business metrics, that's when you know it's really working.

"We're measuring our business outcomes like how many quotes underwriters are getting out the door and how much business have they bound. We also meet with Sixfold every month to look at quality metrics."
‍
─Amy Nelsen @Zurich North America

The Final Wisdom 

Scaling AI in underwriting isn't primarily a technology challenge, it's a people and process challenge. Both Amy and Jim closed with the same underlying message: be preapred for that thing change quickly in the world of AI, don't be afraid to fail, and don't stay stuck in proof-of-concept mode forever.

The insurers that will succed at scaling AI are the ones that move deliberately, learn fast, and bring their underwriters along for the ride from day one.

Watch the video recording of the entire webinar here.

In 2023, Brian, Jane, and I set out to build AI for underwriting. Not as another helper tool, but as the foundation for how underwriting should actually work going forward.

At the time, a few people thought we were crazy. But we believed underwriting was ready. And we believed underwriters deserved better.

That idea has now become real.

Today, I’m excited to share that Sixfold just raised a $30M Series B, led by Brewer Lane, with strategic investment from Guidewire, and continued support from Bessemer Venture Partners and Salesforce Ventures.

From Idea → The AI Underwriting Brain

Fast forward, we’ve built what we originally set out to build:

An underwriting AI brain that global carriers rely on every day.

Sixfold is already trusted by insurers like Zurich North America, Skyward Specialty, Guardian, Generali GC&C, AXIS, and Mosaic.

We’ve processed over 1 million submissions, across 40+ lines of business, supporting insurers representing $265B in gross written premium.

Sixfold is live across North America, the UK, Europe, Latin America, and Australia, underwriting risks across Property & Casualty and Life & Health. Production underwriting at global scale.

AI underwriting isn’t coming someday. It’s here, and Sixfold is leading it.

Underwriters Run the Book, Not the Tasks

We’ve already started to see the shift. Underwriters are no longer spending their days processing information. Instead, they’re making decisions. AI agents execute the work end-to-end. Humans focus on judgment, portfolio performance, and market opportunities.

Or put more simply:

Underwriting operations run on Sixfold. People run the strategy.

That’s the AI Underwriter.

Why Customers Love Sixfold

One of the biggest reasons Sixfold has scaled so quickly is that we don’t ask insurers to rip and replace everything.

Sixfold integrates directly into the tools underwriters already live in. Their workbenches, policy admin systems, existing workflows, and, of course, email inboxes.

Near-zero time to value isn’t a slogan. It’s how we’ve earned trust across the industry.

This Isn’t Theory — It’s Happening Now

What makes this moment exciting is that it’s no longer hypothetical.

Customers are already seeing major impact:

• Skyward deployed Sixfold across 11 underwriting teams and cut quote response time by 35%
• Zurich rolled Sixfold out to 200+ underwriters, saving up to 2 hours per submission

And the real win is what happens next:

• Underwriters are happier because they get time back
• Carriers respond faster with better quotes and better coverage
• Agents and brokers prefer working with those carriers
• Teams win more business and select risk more intelligently
• Competitive advantage starts showing up in combined ratio

Sixfold becomes the underwriting tool you can’t live without.

That’s what “AI transformation” looks like when it’s real.

Why Series B Now

We’ve proven autonomous AI works in real underwriting environments. Now it’s time to scale.

This funding lets us go faster on what matters most:

• More autonomous underwriting agents
• Deeper integrations into carrier workflows
• Portfolio-level visibility
• Global expansion across markets where demand is already there

Underwriting remains the most complex and important function in insurance.

We’re rebuilding it with AI at the core and underwriters in control.

Bring on even more #Funderwriting!

Think post was originally posted on LinkedIn

Sixfold was featured on the big screen at Open AI’s DevDay 2025, recognized for surpassing 100 billion tokens processed. To make it even better, Senior AI Engineer, Drew Das, was honored among global developers for his contributions.

This is a huge milestone for Sixfold, a reflection of the real impact our AI is making in underwriting. But what does 100 billion tokens actually mean in practice? We sat down with Drew to find out.

Can you start by explaining what exactly OpenAI recognized Sixfold for at Dev Day, and what it felt like to see your name up on the screen?

Seeing my name on stage felt like public validation of the engineering team’s hard work. Sixfold is operating at the frontier of large-scale AI in insurance underwriting. We’re not a pilot anymore; we’re in production.

It also hit home the responsibility that comes with it. Yes, we’ve built scale, but now we have to make sure what we produce is high quality and meaningfully used. Sixfold isn’t experimenting with LLMs; we’re running them reliably where accuracy, latency, and auditability really matter.

We’re not a pilot anymore; we’re in production.

What does “100 billion tokens” actually represent in Sixfold’s day-to-day work?

Each token is a fragment of understanding, a piece of text, data, or context that our models interpret and turn into something underwriters can act on.

It signals the volume of underwriting data, documents, broker submissions, and risk information that our platform analyzes and processes through generative AI workflows.

Hitting 100 billion means we’ve moved many workflows off manual underwriting review and into AI. When repetitive work is reduced, underwriters spend more time on relationships, strategy, and higher-value decisions. 

Hitting 100 billion means we’ve moved many workflows off manual underwriting review and into AI. When repetitive work is reduced, underwriters spend more time on relationships, strategy, and higher-value decisions. 

So… what’s next, another 100 billion tokens?

Token count is becoming table stakes. What matters now is how those tokens are applied and the outcomes they create. 

We’re focusing on deeper workflow integration, bringing AI agents that go beyond risk assessment to support decisions, automate workflows, and deliver real-time underwriting intelligence. Our Research Agent is a great example of that.

Considering the high-stakes nature of insurance, every risk insight and decision generated by Sixfold must be auditable and traceable. Our solution isn’t just built for scale, but for governance.

On the engineering side, what does it take to run something at that scale?

From an engineering perspective, scale brings complexity. We’re constantly balancing latency, cost, and accuracy.

Many AI projects stop at the “cool demo” stage, but we’re pushing through the messy engineering: hybrid search, re-ranking, prompt tuning, and evaluation,  all happening under the hood.

Scaling means better signals, more edge cases surfaced, and faster model learning. It’s a flywheel that keeps getting smarter.

Scaling means better signals, more edge cases surfaced, and faster model learning. It’s a flywheel that keeps getting smarter.

Since AI’s introduction in underwriting, it has been about surfacing information: flagging risks, highlighting important insights, and providing recommendations. But there's always been a gap between AI that knows what needs to be done and AI that actually does it.

Sixfold is building AI agents that close that gap: agents that work alongside underwriters to move cases forward autonomously. Referral Agent marks a shift in what Sixfold can do for your underwriting team, starting with one of the biggest bottlenecks we hear about from underwriters: referrals.

“We’re no longer just telling underwriters what to do; we’re helping them do it. This launch represents a major shift in how we drive efficiency and consistency in underwriting — turning “here's what you need to know’ into “here’s what we’ve already done about it”. The Referral Agent is just the beginning of that vision.”

- Alex Schmelkin, Founder and CEO of Sixfold

Where 40% of Cases Get Stuck

When we asked underwriters about their biggest workflow frustrations, referrals came up again and again. 

Every underwriter knows this routine: you spot a case that needs escalation, and suddenly you're building a package. Pull the rules. Cross-reference submission details. Write a detailed email explaining your reasoning. Make sure the approver, such as senior underwriter, has everything they need to make a decision.

It's necessary work, but it takes about an hour per case. With up to 40% of applications requiring escalation, underwriters can spend half their day packaging referrals instead of evaluating risk.

The ripple effects hurt everyone. Brokers wait days for responses while referrals sit in approval queues. Approvers get packages missing key details and have to circle back with questions. What should be a quick handoff becomes a multi-day process that slows everyone down.

AI That Completes the Loop

Referral Agent transforms how this process works. Instead of stopping at identification that a case needs referral, it handles the next steps as well. It executes referrals on its own: flags when a case needs escalation, assembles the complete referral package and drafts a ready-to-send email in your preferred tone.

The underwriter's role changes from package preparation to package review, freeing up time from admin work and letting them focus on more strategic decisions.

The repetitive process that used to take 60 minutes? It now takes 1 minute.

How it works

Sixfold knows the insurer’s unique risk appetite, applies what it’s learned, and clearly shows if and why a referral is required after case analysis is completed.

When the agent flags a case for escalation, it constructs a complete referral package in email form:  a business summary including the company's operational focus and a structured rationale section that walks through each referral guideline breach step-by-step, citing the exact percentages, dollar amounts, and policy thresholds that might have triggered the referral requirement.

With this launch, we’re making the underwriter’s inbox part of the workflow. Underwriters can just forward a broker’s email, with attachments, straight to Sixfold, and the risk assessment kicks off automatically. When it’s time to refer, a pre-drafted email is done, ready to be sent with a single click from the underwriter’s default email provider.

Benefits by Role

For Referrers ‍

- Always know when to refer
- No more repetitive referral tasks 
- Hours back every day for actual underwriting

For Approvers

- Every referral is standardized, making it easier to review
- With complete referral packages, you can decide faster - often same-day
- Automatic audit trail for compliance and training

For Insurers

- Referral guidelines are applied consistently across every team
- Quotes out faster → happier brokers → improved hit ratios
- A process that scales with every underwriter hired

The Broader Vision

‍Referral Agent is part of a shift in what Sixfold can do for your team. In 2024, Sixfold gave underwriters a brain that reads and assesses; now Sixfold equips them with a brain that acts: AI agents that move cases forward on their own.

Each Sixfold agent plugs into your existing workflow to solve a specific bottleneck. Backlog of referrals? Deploy Referral Agent. Team spending hours researching online? The Research Agent does it in minutes. Endless broker negotiations slowing you down? The Negotiation Agent (coming soon) handles it. Use them individually or stack them together,

“Every underwriter knows that sinking feeling of a growing referral queue. With the Referral Agent, that queue clears itself. It proves that AI can take action, not just give advice. It's the first of many agents that free underwriters from processor work so they can become portfolio strategists."

- Lana Jovanovic, Head of Product @Sixfold 

Experience It Live: Try Referral Agent at ITC Vegas in October. Forward an email, watch the risk assessment run, and generate a referral in real time. Book your ITC meeting with Sixfold, or schedule a digital demo.

Life & Health underwriters often have to go through hundreds of pages of medical documents to understand an applicant’s health profile, knowing that one missed detail could lead to the wrong coverage decision.

When we introduced our Life & Health Underwriting AI, we set out to give underwriters everything they need in one place: diagnoses, medications, and procedures pulled from applications and supporting documents, aligned to the insurer’s unique risk appetite. They no longer had to spend time manually going through medical documents. 

But after getting feedback from underwriters across global insurers, we realized something important: presenting information alone isn't enough. What they really need is the full health story, with all the pieces connected. For example, if a medication appears, they need to know the full context around it: how often it was prescribed and any related diagnoses or procedures.

That’s why we’re upgrading our Underwriting AI with Conditional Insights and Clinical Data, designed to reflect the way underwriters think about the overall health profile.

What’s New?

Conditions: From Medical Facts to the Full Story

Conditions completely change how Sixfold’s insights are presented to underwriters. 

Previously, all relevant data, like Personal Health, Medications, Procedures, and more, appeared as individual facts. While surfacing this information is essential, it didn’t show underwriters how it all connected.

The thing is, Life and Health underwriters don't analyze each fact in isolation; they think about how it fits into the bigger picture. What does this medication suggest? How severe is the condition? How does it all connect?

That’s why Sixfold now brings together all relevant information under a diagnosed condition, including:

• Medications and ongoing treatment
• Procedures and lab results
• The condition’s full history, with context and progression over time
  

For example, take Gastritis, an inflammation of the stomach lining that can cause pain, indigestion, and discomfort. An applicant might have been diagnosed with it a while ago, is taking medication such as Pantoprazole, and could have undergone procedures like Endoscopies five years ago.

Instead of treating these details as in isolation, Sixfold now recognizes they’re all part of the same conditions story. This mirrors exactly how an experienced underwriter would naturally connect the dots, seeing not just health facts, but the bigger picture of an applicant’s health history.

“This release has been a huge focus for our team, and the feedback from early users has been very positive. They’ve shared firsthand how impactful it is to have a single experience that brings together every aspect of an applicant’s medical history.” 

- Noah Grosshandler, Product Manager at Sixfold.

Want a closer look at how Conditions work? Join our live product demo on September 11th.

Core Clinical Data: Lab Insights and Historical Trends

Underwriters often have to go through dozens of lab results to answer: Does this applicant have an underlying condition? Are the results concerning? Could they worsen over time?

Core Clinical Data brings all of that information into one place, instantly. It pulls information found in lab results and medical records uploaded to Sixfold, presenting a pre-defined set of health indicators commonly tied to high-risk conditions such as: Vitals, Cardiovascular Health, and Hematology.

It gives underwriters instant and standardized insight: lab values, normal ranges, and historical progression, making it easier to assess the presence, progression, and severity of chronic conditions.

The impact? Core Clinical Data gives underwriters a snapshot of the applicant’s health at a glance, meaning time saved in reading lab reports that can be used to actually bind accounts. With immediate access to historical trends and key lab indicators, underwriters can make faster and more accurate decisions. 

How Guardian Cut Review Time in Half

Guardian, one of the largest life insurers in the U.S., faced a common challenge: manual case reviews slowed down underwriters and created bottlenecks in the underwriting process.

By adopting Sixfold for its Disability line, Guardian was able to automatically extract medical data, triage information faster, and speed up case assessments end-to-end.

The impact: a 50% reduction in review time, freeing underwriters from being stuck reviewing medical records and letting them focus on risk decisions. Read more about the results Guardian has seen here. 

Now, Guardian is expanding the program across more business lines, and you can see why! Join our Life & Health Product Demo on September 11th, where we’ll showcase how Sixfold works for life & health insurance underwriting.