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At Lloyd’s: The Future of Underwriting
Sixfold hosted an event at Lloyd’s in London focused on the next generation of underwriters, featuring speakers and insights from Berkley, Victor Insurance, Generali GC&C, and Torch Underwriting.

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Celebrating Year One: Q&A with Co-Founder Jane Tran
We chatted with Sixfold's Co-founder & COO about the first year of Sixfold and what's next.
We had an opportunity to chat with Sixfold's Co-founder and COO Jane Tran about the company’s amazing first year and the vision for the years to come, as well as her career journey, giving back, and tips on running a fast-paced AI startup.
What was your first job and how did that influence your career?
My very first job ever was as a cashier at an Italian deli around the corner from my parents’ house.
I think everyone should do a service job because it emphasizes the importance of good customer service like how to treat people. I also learned how to be quick because it's New York. New Yorkers don’t like to wait for their Bacon, Egg, and Cheese.
Walk us through your career journey from the Italian deli to co-founder and COO at Sixfold.
I’ve had a good mix of enterprise and startup experience. I started my career at JP Morgan as part of their rotational analyst program. One of my last rotations was with the Turnaround & Process Improvement team for the Chief Information Officer—that’s where I fell in love with tech. I worked on really cool projects like improving the eDiscovery process and improving data governance. I had a blast.
After that, I spent several years at Marsh and MetLife working with the CIOs on different strategy and planning projects before I decided to give startups to go. I was on the founding team at Unqork where I was Head of Solutions before becoming COO.
When I decided to leave Unqork, I kept in contact with Alex [Schmelkin, founding team at Unqork, and co-founder of Sixfold]. When he came up with the idea for what would become Sixfold, he asked me to join him to get this idea off the ground.
What does the name Sixfold mean and who came up with it?
So, all kudos due to Alex’s daughter Nina Schmelkin for that! She was doing a project for school around patterns. A sixfold pattern is considered one of the most interesting, naturally occurring patterns—snowflakes are a sixfold pattern. And so, when it came to choosing a name for the company, we were thinking about AI and the role that patterns play, and “Sixfold” seemed like an ideal fit.
Sixfold just turned one year old. How would you describe year one?
A ton of fun! We’re building really tangible use cases using cutting-edge tech. This first year has reinforced the importance of anchoring your work in first principles. AI is obviously super hot and evolving at warp speed, but we can't ignore the things that support great software development and great user experiences. That meant getting that foundation and discipline in place while at the same time making room for extensive R&D and a ton of iterations.
We learned a lot. We tweaked a bunch. And I think we found product market fit. Our early customers are already starting to see value, and I’m really excited to see where that grows this year.
Do you have any notable “wow” moments from the first year?
Yeah, when we delivered our first end-to-end underwriting pilots and heard the underwriters say “we were able to complete this task in a fifth of the time.” I particularly love hearing how much they trust the tool.
Hearing that first positive user feedback feels like a major achievement! And, obviously, the recent closing of our Series A funding round.
Who are your role models and how did they influence your career?
My parents. My mom runs a small business in kitchen supplies with her siblings — it was one of those things where they just sort of fell into it. They knew they could offer a really good product and create a fit within the market. They understood what customers wanted and knew that they could manufacture it. So they just went for it. That takes a lot of bravery. On the flip side, my dad hung wallpaper for a living. He's retired now, but he had that hard work ethic and true care for his craft. He developed a reputation for excellence and really worked his way up.
I think the combination of entrepreneurship, work ethic, and quality very much influences who I am.
A common conversation for startups is balancing “the need for speed” with employee happiness. How do you build that balance into the company culture?
Unfortunately, I don't have a magic formula. I would say that from the get-go, Sixfold’s three founders — Brian, Alex, and myself — anchored ourselves on our Mission and a handful of operating principles like putting the customer first and being direct while being kind. We try to surround ourselves with people who share those principles so that naturally becomes the culture of the company.

The three of us really care about who works for us and how we all work together. Sometimes we may not have the best balance, but we always strive to be better. As founders, we care a lot about our work, but we also care deeply about family, friends, and life outside work. We understand that people who work with us have the same need for a balanced life outside work.
Do you have any tips when it comes to hiring?
Instinct is a huge part of it. It’s also helpful to have a great HR team in place — kudos to Marie [Sixfold’s HR Business Partner] for doing a lot of the initial groundwork, so by the time a candidate gets to me, they fit a lot of our criteria for that role. From there, a lot of it just comes down to just instinct. Ask yourself if they'll fit within the culture of this company.
Tell us about your mentoring work for different startups and organizations.
I'm on the board of directors and co-chair for an organization called Womankind. It helps survivors of gender-based violence in New York, with a focus on the AAPI community. They've been around for more than 40 years. They started with a single hotline for the NYC area, but have expanded to serve thousands of women every year across the US as one of the few true end-to-end organizations. So families get to stay together. They get legal help. They get job placement. Their kids have a safe place to be while they're figuring out, you know, the next steps. I'm really proud to be part of that organization.
I've also mentored and advised a few other early-stage startups that I think are doing something new and interesting. This also helps me to understand what else is out there in the ecosystem. I’ve mostly been focused on B2B enterprise throughout my career, so I like learning about retail or other sectors.
I love being around people who are building interesting things. It’s super fun and it can be super informational too.
What are your top work tools that you feel like you couldn’t do without?
I don't do a lot of the things that “productivity hackers” do. I would say Apple Notes and Google Tasks are central to my workday. I keep extensive notes on my meetings— so that’s a lot of Apple notes. And then, for the important things with a deadline, I'll set up a Google task or calendar reminder. And that's how I organize.
What are you excited about for Sixfold’s second year?
This year will be about continuing to mature our product and getting a lot of new customer use cases live.
We're working with a lot of great people and a lot of great customers. I’m looking forward to showcasing what we can do within this market and at this fidelity — a year ago, I don't think anyone would have thought that we’d be able to do what we’re doing, so I can’t wait to see what the next year or two will bring!
Want to work with Jane and the rest of the Sixfold team? Check out our career page.

Announcing Sixfold’s Series A Led By Salesforce Ventures
This $15 million injection of capital will accelerate the journey to a new era of AI-powered decision-making in insurance underwriting.
Just 12 months ago, we introduced Sixfold and its vision to the world. Today, we’re thrilled to announce a $15 million Series A investment led by Salesforce Ventures with participation from Scale Venture Partners and our initial seed investors Bessemer Venture Partners and Crystal Venture Partners.
With these additional resources, Sixfold will expand our already exceptional team of engineers to further enhance our products and accelerate our R&D efforts. On the business & operations side, we will broaden our offerings and grow our footprint beyond North America to the United Kingdom and European Union.
Most importantly, this new capital injection will advance our mission to overcome today’s most pressing underwriting challenges, not by iteration, but by building a new end-to-end risk analysis paradigm. That’s a big statement, I know. But we didn’t pick the name “Sixfold” out of modesty.
Year one of building insurance’s most consequential tech
In our inaugural blog post, I pledged that Sixfold would “focus on one of the most intractable challenges in insurance: the inefficiency of underwriting” and our team has backed up this promise with a year’s worth of accomplishments.
We’ve developed a patent-pending AI that rapidly translates carriers’ unique underwriting guidelines into digital risk models, regardless of what form those guidelines take. This is Sixfold’s superpower, but far from our only bit of AI magic.
Leveraging 10 proprietary models, our platform surfaces appetite-aligned risk signals from disparate sources and independently “connects the dots” to generate natural language summarizations and recommendations. All our hard engineering work has resulted in unquestionable business value. In just one year, Sixfold has boosted underwriting capacity for our customers by a factor of 10, accelerated data collection by 2,000x, sliced submission-to-quote cycles from hours (sometimes weeks) to mere minutes, and pushed our platform accuracy to an industry-leading 94% so our customers can precisely assign NAICS/SIC codes at scale.
Sixfold is uniquely posed for continued growth with top-tier global partners in the year to come. We were named a winner of The 2024 Zurich Innovation Championship, the industry’s largest open innovation contest. As one of only 9 winners selected from more than 3,000 global applicants, our team will participate in the Championship’s elite accelerator program to develop a new commercial underwriting solution.
Our Innovation Championship win was a powerful validation of Sixfold’s approach from a storied industry leader, and it wasn’t even the only one in 2024—in March, Sixfold was selected for the exclusive Lloyd’s Lab accelerator program (out of their largest-ever pool of applicants). Our team is currently working with Lloyd’s to develop innovative solutions for the world’s leading insurance and reinsurance marketplace, which will be invaluable as Sixfold expands into the UK and beyond.
Writing the next chapter in underwriting
Over the past year, we’ve grown from a team of three to a staff of 18, with more additions to come. In the near term, we’re focused on bringing on seasoned tech leaders to guide our continued success, as exemplified by the recent addition of Ian P. Cook, PhD, Sixfold’s first full-time head of AI. By adding select talent to our elite team, there’s no underwriting challenge we won’t overcome.
I’m ridiculously proud of what this team has accomplished and excited about everything we will accomplish utilizing this latest fund round as a jumping-off point.
I want to thank Laura Rowson, Nowi Kallen, and the rest of the Salesforce Ventures team for seeing the unique potential of our vision, or as Laura generously put it in our press release, for seeing Sixfold “as a company capable of transforming the insurance industry.” We’re beyond excited to work with Salesforce Ventures to accelerate our growth and materialize those changes.
And, of course, a huge thank you to Alex Niehenke at Scale Venture Partners and for continued support from our initial backers Charles Birnbaum & Jeremy Levine at Bessemer Venture Partners and Jonathan Crystal & Stephen McGovern at Crystal Venture Partners.

If you haven’t yet had a chance to see what our platform can accomplish, there’s no better time to get started. Reach out for a personalized demo. We can’t wait to show you the future of underwriting.
This article was originally posted on LinkedIn

Sixfold Is Named a Zurich Innovation Championship Winner
Sixfold has been named a winner of the 2024 Zurich Innovation Championship and will participate in a four-month accelerator program to develop a new commercial underwriting solution.
I’m thrilled to announce that Sixfold has been named a winner of this year’s Zurich Innovation Championship! Since 2018, Zurich Insurance Group has overseen an annual “collaboration program” with select startups from around the world to develop new offers and services for their customers. The yearly Championship has rapidly expanded to become the industry’s largest open innovation contest with thousands of applicants from over 30 countries resulting in more than 50 active initiatives implemented through Zurich Insurance’s global business.
Celebrated for Pioneering Innovation
Sixfold was only one of nine teams selected out of a pool of more than 3,000 global applicants to take part in the accelerator portion of the Championship. Our team will take on the “Commercial Insurance” challenge to engineer technical solutions that “improve transparency and accountability, enhance risk management capabilities, and foster sustainability transition through a culture of trust and innovation.”
For the next four months, our team will collaborate with leaders from Zurich North America (ZNA) to build AI-powered risk analysis & summarization solutions to augment underwriter workflows through the automation of high-volume (but not necessarily high-value) tasks.
Improving Insurance Efficiencies
Unlike traditional accelerator programs, which focus on product development, the Innovation Championship aims to accelerate the adoption of a new solution within Zurich Insurance’s global business. We’re thankful to the leadership at Zurich Insurance for believing in Sixfold’s mission and our team, and we look forward to building an amazing solution that results in improved efficiencies that benefit Zurich’s customers, insurance brokers, and other stakeholders.
This collaboration comes only two months after Sixfold’s selection to participate in the 12th cohort of Lloyd’s exclusive accelerator program, Lloyd’s Labs, which kicked off in April and we will be demoing in July.
We’ve only just begun Sixfold’s second year — and it’s turning out to be a BIG one!

AI in Insurance Is Officially “High Risk” in the EU. Now What?
The new EU AI Act defines AI in insurance as “high risk.” Here’s what that means and how to remain compliant in Europe and around the world.
The European Parliament passed the EU Artificial Intelligence Act in March, a sweeping regulatory framework scheduled to go into effect by mid-2026.
The Act categorizes AI systems into four risk tiers—Unacceptable, High, Limited, and Minimal—based on the sensitivity of the data the systems handle and the crucialness of the use case.
It specifically carves out guidelines for AI in insurance, placing “AI systems intended to be used for risk assessment and pricing in [...] life and health insurance” in the “High-risk” tier, which means they must continually satisfy specific conditions around security, transparency, auditability, and human oversight.
The Act’s passage is reflective of an emerging acknowledgment that AI must be paired with rules guiding its impact and development—and it's far from just an EU thing. Last week, the UK and the US signed a first-of-its-kind bilateral agreement to develop “robust” methods for evaluating the safety of AI tools and the systems that underpin them.
I fully expect to see additional frameworks following the EU, UK, and US’s lead, particularly within vital sectors such as life insurance. Safety, governance, and transparency are no longer lofty, optional aspirations for AI providers, they are inherent—and increasingly enforceable—facets of the emerging business landscape.
Please be skeptical of your tech vendors
When a carrier integrates a vendor into their tech stack, they’re outsourcing a certain amount of risk management to that vendor. That’s no small responsibility and one we at Sixfold take very seriously.
We’ve taken on the continuous work of keeping our technology compliant with evolving rules and expectations, so you don’t have to. That message, I’ve found, doesn’t always land immediately. Tech leaders have an inherent “filter” for vendor claims that is appropriate and understandable (I too have years of experience overseeing sprawling enterprise tech stacks and attempting to separate marketing from “the meat”). We expect—indeed, we want—customers to question our claims and check our work. As my co-founder and COO Jane Tran put it during a panel discussion at ITI EU 2024:
“As a carrier, you should be skeptical towards new technology solutions. Our work as a vendor is to make you confident that we have thought about all the risks for you already.”
Today, confidence-building has extended to ensuring customers and partners that our platform complies with emerging AI rules around the world—including ones that are still being written.
Balancing AI underwriting and transparency
When we launched last year, there was lots of buzz about the potential of AI, along with lots of talk about its potential downside. We didn’t need to hire pricey consultants to know that AI regulations would be coming soon.
Early on, we actively engaged with US regulators to understand their thinking and offer our insights to them as AI experts. From these conversations, we learned that the chief issue was the scaling out of bias and the impact of AI hallucinations on consequential decisions.

With these concerns in mind, we proactively designed our platform with baked-in transparency to mitigate the influence of human bias, while also installing mechanisms to eliminate hallucinations and elevate privacy. Each Sixfold customer operates within an isolated, single-tenant environment, and end-user data is never persisted in the LLM-powered Gen AI layer so information remains protected and secure. We were implementing enterprise AI guardrails before it was cool.
I’ve often found customers and prospects are surprised when I share with them how prepared our platform is for the evolving patchwork of global AI regulations. I’m not sure what their conversations with other companies are like, but I sense the relief when they learn how Sixfold was built from the get-go to comply with the new way of things–even before they were a thing.

Sixfold Selected for Lloyd's Lab's Latest Cohort
Sixfold was one of just a dozen global insurtechs invited to join Lloyd’s exclusive 10-week accelerator program.
I’m beyond excited to announce that Sixfold has been officially selected to take part in the 12th cohort of Lloyd’s InsurTech accelerator program, Lloyd’s Lab.
Lloyd’s Lab was recently recognized as a top-25 European start-up hub by the Financial Times and Statista and ranked the very top insurance-focused accelerator out of 19 countries and +2,000 organizations.
The program will give our team the opportunity to collaborate with Lloyd’s mentors to develop innovative solutions for the world’s leading insurance and reinsurance marketplace. Over the course of the 10-week “fast-track, fast fail” program kicking off in late April, our team will build, test, and iterate innovative solutions that “challenge how we do things and help the Lloyd’s market better serve its customers.”

Sixfold was one of just 22 insurtechs invited to travel to London to take part in Lloyd’s “Pitch Day” event. This year saw the largest-ever application pool for the program—Pitch Day invitees had to be culled down from more than 250 applications submitted by insurtechs spanning 33 different counties.
For our pitch, I showcased how much we have built to serve underwriters in the past 10 months to 1,000-plus virtual and in-person attendees from across the Lloyd’s market ecosystem. We were selected into the program as one of only 12 teams by a panel of market leaders, mentors, and the Lab team, and we were the only underwriting solution to be accepted into the program!
Members of Sixfold’s product and design teams will spend 10 weeks working out of the iconic Lloyd’s building in London. We will focus our efforts on accelerating and optimizing triage and risk appetite match capabilities within the scale of Lloyd’s markets.
We’ll demo the fruits of our accelerator labor to the entire Lloyd’s market in early July—stay tuned for details!
Lloyd’s Lab unique approach to fostering global innovation is helping to tackle some of the world’s biggest insurance challenges. Progressing the Lab’s mission of supporting innovative insurance solutions across the globe, this latest cohort focuses on developing solutions to some of the biggest risks faced by businesses and communities in the Americas such as challenges arising from natural hazard prediction to risks associated with cybersecurity.
Thank you to Lloyd’s for believing in our vision and helping us bring it to fruition. We can’t wait to show the entire Lloyd’s market—and the rest of the world—what we have in store.
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Beyond Chatbots: A Gen AI Solution for L&D Underwriting
Gen-AI-powered L&D underwriting goes beyond chatting with bots. This view has shaped our design ideology, emphasizing simplicity, context, trust, and fun.
Today, life & disability carriers have access to more data from more data sources than ever, but the processing of all that data has paradoxically decreased efficiency and limited underwriting capacity. The industry has wisely turned to gen AI to help it reap the rewards of the modern data abundance while minimizing the cost.
In our view, gen-AI-powered underwriting isn’t about conversing with chatbots, it’s about collaborating with a platform that understands exactly what you need and exactly how to get it. But how should a platform like that function? What would it even look like? We started the process of answering those questions by interviewing dozens of underwriters to understand their frustrations, goals, and how other tools have failed them in the past. This input has guided our approach to design built around simplicity, context, trust, and fun.
Simplicity
Many L&D carriers rely on automated extraction tools and/or offshore teams for their data-processing needs. These result in long multi-page reports, which are typically just ordered lists of data. Underwriters are left to rifle through these tomes to pull out relevant info. Sixfold eliminates these overly manual tasks by injecting AI throughout the underwriting process.
We use cutting-edge AI to independently build a virtual model of carriers’ unique risk appetites, so the platform can understand what constitutes negative or positive risk signals for that carrier. The platform taps a different set of purpose-built AI models to process ingested data and gracefully surface precisely what information underwriters need — and nothing else.
How does this AI wonder translate into design? We’ve leaned hard into “inconspicuously helpful.” The best AI is one that doesn’t make a show of itself, but can be depended upon to solve problems when called into action. More old-school British butler, and less Robin Williams’ genie from Aladdin. From a design perspective, that means elevating minimalism and simplicity.
Underwriters never see the AI hard at work ingesting data from disparate sources (APS files, MIB reports, labs, etc.). And they shouldn’t have to. All they want to see are easily scannable bits of appetite-aligned information in a unified dashboard experience. Leave the sausage-making to us, enjoy your hotdog.

This effortless minimalism extends to every part of the platform. On the case list page, underwriters can peruse a list of applicants with clear visual cues signifying which cases are closely aligned with underwriting criteria and which aren’t. In a previous technological era, underwriters had to invest time in scrutinizing each and every applicant with limited ability to triage, leading to reduced productivity. With Sixfold, they can focus their efforts on the biggest impact.

Context
Traditional data processing & ingestion treats all information equally. Taking a daily multivitamin is, for example, given with the same “weight” as immunosuppressants taken after an organ transplant. “Flattened” data reports, no matter how thorough, require underwriter intermediation to pick out the relevant through lines.
We can do better in 2024.
Sixfold taps a medley of nine AI models to identify relevant data points from disparate sources and “connect the dots” between them. It’s the difference between, say, mentioning an applicant has diabetes versus summarizing how it’s being managed, e.g., “applicant was diagnosed with diabetes in 2015, but it is being adequately managed through diet and insulin.”
We haven’t merely replaced one form of summarization with an AI-powered one. We use gen AI prudently and solely in service of accelerating decision-making. Our goal is to present underwriters with as little information as possible (or, rather, just the right information) so they can focus their energies on making informed decisions.
Concise auto-generated explanations are placed front and center, but underwriters can always dive deeper into specific information as needed (e.g., the platform may let you know that recent cholesterol readings were acceptable, but you have the option to dive into the readings from the last few labs).

Trust
The best underwriters are detail-oriented, and they deserve tools that meet (or better yet, exceed) their standards of thoroughness. Underwriters using Sixfold should be confident that everything has been scrutinized as thoroughly as if they did it themselves—if not more!
We accomplish this by showing our work. Transparency is baked into the Sixfold UX. We provide sourcing of all surfaced risk factors and conclusions, right down to the source and page so underwriters know precisely where a conclusion came from, and why it was arrived at.
And a little bit of fun
We want engagements with our platform to feel like working with your favorite coworker. You know the one we’re talking about right? The one that gets things done, but throws in a little light-hearted banter and joking around to improve your day just a bit.
Going through medical records isn’t what most people consider enjoyable. So we injected some moments of surprise and delight that can bring the joy back to underwriting. Our platform includes small flourishes that we hope provide a little levity.

Throughout the site, we’ve included illustrations of friendly robots collaborating with humans and empowering the humans to do more. The overriding theme of this aesthetic? Clay. Why clay? It feels deeply human, handmade with little imperfections that add character. We believe that AI can liberate humans from rote work (which is better handled by machines anyway) so they can emphasize their uniquely human qualities. The machines aren’t going to take over our jobs – they’re going to free us to bring humanity back to the work we do.
Want to see the platform in action? Watch our on-demand product demo for a live walkthrough of Sixfold’s Life & Disability offerings.