S

Sixfold

AI-powered underwriting automation for insurance SaaS

Vice President of Product

Full-Time
$245k - $285k+ Equity
Expert
New York, NY, USA
HybridHybrid position based in NYC, with about half the company working in the office 3–4 days a week.
ProductProduct Management
No H1B Sponsorship

About the job

Requirements
  • Build something directly, including writing prompt chains, running evaluations, and working with customers.
  • Take products from zero to production and understand the impact on annual recurring revenue, retention, or adoption.
  • Prototype solutions and validate them with real customers, iterating based on feedback.
  • Maintain a clear 12-month product theme while adapting the mechanisms and roadmap as conditions change.
  • Use AI heavily while applying independent judgment about risk and what is worth building.
  • Improve existing teams and products, recognizing what is working before deciding to replace it.
Responsibilities
  • Set the direction for AI-native underwriting at Sixfold and maintain a 12-month theme while adapting tactics frequently.
  • Build early versions of new ideas, including prototypes, working demos, and lighthouse customer tests, before asking the team to scale them.
  • Stay current on developments in AI and form informed views about where the technology is heading.
  • Represent Sixfold's perspective on the future of underwriting with customers, partners, and the industry.
  • Take ownership of the existing product and team and raise the bar on how they operate.
  • Partner closely with design and engineering to maintain prototyping speed while avoiding technical debt.
  • Develop a strong understanding of the risk-reasoning AI and identify where the product has gaps.

About the company

Sixfold.ai provides software-as-a-service tools for the insurance industry that automate and assist underwriting tasks using generative AI. The main product is a co-pilot that follows the insurer’s underwriting manual and rules, helping underwriters work faster while maintaining compliance and traceability. It connects to existing underwriting workflows and automates repetitive tasks so underwriters can focus on more strategic decisions. Compared to competitors, Sixfold.ai combines a rule-driven, compliant AI assistant with clear audit trails and customization options, designed to fit the specific underwriting guidelines of each insurer. The company’s goal is to improve accuracy, speed, and decision-making in underwriting, enabling insurers to modernize operations and increase capacity without sacrificing compliance.

Company Size

51-200

Company Stage

Series B

Total Funding

$51.5M

Headquarters

New York City, New York

Founded

2023

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Simplify's Take

What believers are saying

  • January 2026 Series B raised $30 million from Brewer Lane, Guidewire, Bessemer, Salesforce.
  • August 2026 Sollers partnership expands implementation capacity across Europe, the UK, and North America.
  • Sixfold claims 1.5 million submissions processed and 90%+ customer adoption, supporting sales momentum.

What critics are saying

  • Guidewire's June 2026 investment makes a powerful channel partner and eventual competitor.
  • Sixfold's exact underwriter gains depend on carrier data quality and disciplined human oversight.
  • If insurers reject autonomous underwriting in 2027, Sixfold becomes a workflow feature, not a platform.

What makes Sixfold unique

  • Sixfold's June 2026 AI Underwriter embeds directly into carrier workflows and Salesforce.
  • Its underwriting brain captures carrier decisions, creating institutional memory competitors cannot easily copy.
  • Customers include Zurich, AXIS, Generali, Guardian, and Skyward Specialty across global lines.

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Benefits

  • Company Equity
  • 401(k) Company Match
  • Mental Health Support
  • Wellness Program

Growth & Insights and Company News

Headcount

6 month growth

2%

1 year growth

-1%

2 year growth

2%
Cloud Awards
Oct 13th, 2026
2026 A.I. Awards winners.

2026 A.I. Awards winners. Sixfold. "Sixfold's ability to move beyond document extraction and deliver genuine underwriting intelligence, helping insurers make faster, more informed, and more consistent decisions at scale, was demonstrated through exceptional evidence of real-world adoption and measurable impact. The solution stood out at The AI Awards for combining AI-powered reasoning with carrier-controlled autonomy in a highly regulated industry, allowing organizations to increase efficiency without sacrificing governance or trust. Multiple customer examples demonstrated significant business outcomes, while the platform showed strong adoption, scalability, and practical value in production environments. Overall, Sixfold presented an exceptionally complete and commercially proven AI solution." Jon Whittall, Judge "Sixfold impressed the judges at The AI Awards with an AI solution built around the highly specialized demands of insurance underwriting. By combining sophisticated artificial intelligence with deep understanding of underwriting workflows, Sixfold helps professionals navigate complex risk information and reach informed decisions more efficiently. Its depth of specialization, practical application and clear understanding of the industry it serves made it an outstanding example of purpose-built AI." Annabelle Whittall, The Cloud Awards COO

Insurance Post
Aug 27th, 2026
Sixfold brings AI underwriting into Salesforce workflows.

Sixfold brings AI underwriting into Salesforce workflows. * * By Emma Ann Hughes * 27 Aug 2026 * Indicative reading time: 1 minute Sixfold has partnered with PS Advisory to bring its artificial intelligence underwriting capabilities directly into Salesforce. The partnership centres on a custom MuleSoft connector developed by PS Advisory, which provides bidirectional connectivity between Sixfold and Salesforce. The integration allows submission data Show password You may also like. More on technology. * 20 Aug 2026

FinTech Global
Aug 14th, 2026
Sixfold and Sollers team up on AI underwriting.

Sixfold and Sollers team up on AI underwriting. August 14, 2026 Sixfold, the AI underwriting InsurTech trusted by global insurers, has entered a strategic partnership with Sollers Consulting, the international insurance technology consultancy, aimed at helping carriers speed up their underwriting transformation. The tie-up brings together Sixfold's AI-driven risk assessment capabilities with Sollers' consulting and implementation know-how, giving insurers a combined offering of AI, advisory support and technology delivery under one transformation programme. The two firms will jointly support insurer modernisation projects across Europe, the UK and North America, enabling carriers to automate the intake of submissions, evaluate risk against their own appetite, and receive clear, explainable underwriting recommendations without needing to step outside their current systems and workflows. Several joint engagements are already under way, each shaped around the specific technology and underwriting needs of the insurer involved. Sixfold's existing client base includes major P&C and L&H insurers such as Zurich, Skyward Specialty, AXIS and Generali GC&C. The firm has so far processed upwards of 1.5 million submissions spanning more than 50 lines of business, with customers reporting processing speed gains of between 50% and 97%, hit ratios climbing by at least 15%, and gross written premium per underwriter rising by as much as 30%. Rather than displacing insurers' existing underwriting infrastructure, the platform is designed to work alongside it. Sixfold's technology is built to work through submissions in a manner comparable to an experienced underwriter, flagging recommendations before a file is even reviewed by a person. Its pre-loaded underwriting expertise and ability to integrate with tools already in use mean it can start delivering results immediately. The company serves L&H and P&C carriers, MGAs and reinsurers across North America, South America, Europe and Australia, counting Guardian and New York Life among its customers. Sixfold Head of Partnerships Roger Ferrandis said, "Insurers should not have to replace the systems their underwriters already use to get value from AI. Sixfold works within those systems and comes with underwriting knowledge built in from day one. Sollers know how those systems are set up and used. Together, that gets insurers to better underwriting results faster." Sollers Head of Underwriting Jakub Śliwiński said, "We've built Sollers' underwriting practice around the belief that the right technology, applied to the right part of the process, delivers outstanding results. Sixfold makes submission handling faster, more consistent and more intelligent. Together, we can help insurers achieve measurable results quickly while laying the foundations for underwriting transformation." Enjoying the stories? Investors. The following investor(s) were tagged in this article.

The SaaS News
Jun 15th, 2026
Sixfold raises $30M Series B.

Sixfold raises $30M Series B. Sixfold raises $30M in a Series B round led by Brewer Lane to scale its agentic AI underwriting platform for global insurance carriers. Updated June 14, 2026 Sixfold, an insurtech company providing an AI underwriting platform for insurance carriers, has raised $30 million in a Series B funding round. This new capital brings the company total funding to more than $50 million. The startup focuses on providing agentic AI components that integrate with existing underwriting workbenches and policy administration systems to streamline underwriting flows. Investors. The funding round was led by Brewer Lane, with strategic investment from Guidewire and participation from Bessemer Venture Partners and Salesforce Ventures. Sixfold use of funds. The company plans to use the new capital to accelerate the development of its AI underwriting product, expand research and engineering efforts for its autonomous underwriting agents, and scale its commercial operations across North America, Europe, Latin America, and Australia. About Sixfold. Founded by Alex Schmelkin and Jane Tran, Sixfold provides an AI platform designed to automate and augment the underwriting process for insurers. The software integrates directly into existing carrier workflows to improve quote response times and underwriting efficiency without requiring changes to core systems. Funding details. Company: Sixfold Raised: $30M Round: Series B Funding Date: June 12, 2026 Lead Investor: Brewer Lane Additional Investors: Guidewire, Bessemer Venture Partners, Salesforce Ventures Company Website: https://sixfold.ai Software Category: Insurtech Source: https://letsdatascience.com/news/sixfold-secures-30-million-series-b-funding-c26ace54 Updated June 14, 2026

The Insurer
Jun 12th, 2026
Exclusive: Sixfold launches AI underwriting agent with straight-through quote and bind capability.

Exclusive: Sixfold launches AI underwriting agent with straight-through quote and bind capability. By James Thaler Published: Fri 12 Jun 2026 Insurtech Sixfold is launching the AI Underwriter, an agent that learns an individual carrier's book and appetite, recommends the next action on each submission and can be configured to take cases straight through to quote-ready and bind-ready materials. The AI Underwriter will be available to P&C insurers from Monday, Sixfold confirmed in a statement to The Insurer. The agent feeds every decision an insurer's underwriters make back into that carrier's deployment, building what Sixfold describes as institutional memory that existing data ingestion, policy and workbench systems have not been built to capture. Each insurer's book is walled off, and one carrier's data is never used to train another's system. Each carrier weighs how much of the work the agent handles autonomously. When configured for straight-through processing, cases can be processed into quote-ready and bind-ready output for acceptance by a broker or client. The customer's underwriters provide direction, judgment and oversight, remaining accountable for how the agent is governed. Sixfold's customers represent $270 billion in gross written premium and include Skyward Specialty, Zurich Insurance, Generali Global Corporate & Commercial, Guardian, Axis and New York Life. The company has processed more than 1.5 million submissions across more than 50 lines of business since 2023. Sixfold said its customers have historically seen processing times improve by between 50% and 97% and hit ratios rise by 15% or more, with gross written premium per underwriter climbing by up to 30%, gains the company chalks up to its platform. The insurtech also reported underwriting adoption rates of 90% or higher, measured as actual users against expected users. Founder and CEO Alex Schmelkin said the product was built around what underwriters need at the moment a submission arrives, rather than documents bouncing between systems or static dashboards. "They don't need a digitized version of the application, broker documents moved from their inbox to another system, or a dashboard with data that was current last week," Schmelkin said. "Data ingestion and workflow solutions are trying to heal the symptoms of inefficient underwriting without affecting the cause. "Instead, our users told us that what they need is to understand the risk in the full context of their current book, the broker, and the guidelines, and to be presented with a clear next step. Right there, at the moment a decision is being made. That is what the AI Underwriter does." When a submission comes in, the agent extracts and cleans the data, identifies missing information, evaluates appetite and portfolio fit and draws on what it has learned about the broker and risk class before producing a recommendation, explaining its rationale and suggesting a next step. The system is built around what Sixfold calls its underwriting brain, developed over three years alongside some of the world's largest insurers. The underwriting brain arrives trained on the standards behind professional underwriting credentials, underwriter reasoning patterns and a curated ground truth library, helping it work across lines of business and industries. A select group of insurers worked with the agent on live submissions ahead of the launch, with Sixfold reporting that it performed the majority of the underwriting analysis required to evaluate submissions within Skyward Specialty's E&S brokerage property business. Its responsible AI program was built from the bottom up, spanning governance controls and regulatory engagement, so that every deployment begins with trust from carrier risk and compliance teams, the company said. John Burkhart, Skyward Specialty's president of U.S. property and casualty, said the carrier is incorporating the agent into its bionic underwriting strategy as it looks for partners that can scale alongside the business and free underwriters to focus on what they do best. "We are equipping our underwriters with richer context that enhances their decision-making while keeping human expertise firmly at the center of the process," Burkhart said. Matthew Richardson, global head of operations and IT at Generali GC&C, said the product is built alongside underwriters, shaped by how the job works in practice and fast enough to change quoting timelines. "Sixfold helps us quote risks in minutes instead of days or in some cases weeks," he said. Sixfold raised $30 million in Series B funding in January. The round was led by Brewer Lane and included strategic investment from Guidewire, alongside existing backers Bessemer Venture Partners and Salesforce Ventures, as The Insurer previously reported. The raise, which funded development of the AI Underwriter, took the New York-based company's total funding to more than $50 million, following a $15 million Series A led by Salesforce Ventures in 2024. The launch adds to a wave of efforts to embed AI directly inside carrier underwriting operations, where submissions still move through a maze of legacy systems and manual workflows. Schmelkin co-founded Sixfold in 2023 with chief operating officer Jane Tran and chief technology officer Brian Moseley, with the company's wider platform supporting both P&C and life and health underwriting across North America, South America, the UK, Europe and Australia.