Noyo is a San Francisco-based benefits data platform that uses APIs and AI to connect insurance carriers, benefits administration software, and HR teams. It turns the slow, error-prone exchange of employee benefits data into real-time, automated connections, eliminating manual data entry and coverage-impacting errors across the benefits ecosystem.
SimplyInsured is an online health insurance marketplace and benefits administration platform built for small businesses. It lets owners shop, compare, and enroll in medical, dental, and vision plans from 200+ carriers in minutes, then automates employee deductions and payroll syncing - all at no cost beyond the regular premiums. The company powers embedded health benefits inside Square, Gusto, Check, and Patriot payroll.
Robert Smithson is the founder and CEO of Just (just.insure), a Los Angeles pay-per-mile auto insurer that prices drivers on how they actually drive instead of credit scores and zip codes. A Cambridge philosophy graduate and former fund manager, he previously built Genius Sports (sold for $280M in 2018) and the Python platform PythonAnywhere before turning telematics and AI loose on the $300-billion car-insurance market - aiming squarely at making coverage fairer for lower-income drivers.
Michael Ulin is a three-time AI founder and engineer who builds machine-learning companies in heavily regulated industries. He was the founding AI engineer and VP of AI at ZestyAI, whose property-risk models help underwrite trillions in U.S. insured assets, then co-founded and served as CTO of Paxton AI, a generative-AI legal research tool used by thousands of attorneys that raised a $6M seed round in 2023. He now builds from Bend, Oregon, where his current work centers on Trarian, applying AI to patent underwriting, alongside ventures spanning AI forecasting and probabilistic reasoning. He also writes the Substack 'And Yet It Moves' on entrepreneurship and the case for building startups outside Silicon Valley.
Kalepa is a New York-based insurtech building AI software for commercial insurance underwriters. Its flagship platform, Copilot, ingests submissions, extracts and structures messy documents, surfaces hidden risk exposures from billions of data points, and helps underwriters triage, price, and bind business faster and more profitably. Founded in 2018 by Paul Monasterio and Daniel Hillman, the company is backed by Inspired Capital and IA Ventures and works with carriers including Munich Re Specialty, Bowhead Specialty, SECURA, and Canopius.
Spark Advisors is a New York-based technology-enabled Medicare brokerage that builds an all-in-one platform for independent agents, agency principals, and call centers. It combines an agency management system, a Medicare-specific CRM, back-office services, and AI-powered tools to help brokers grow their books of business and keep clients enrolled. The company supports more than 10,000 brokers and powered roughly 250,000 Medicare enrollments in 2025.
Zorro is an AI-powered ICHRA platform that swaps rigid group health plans for a defined-contribution model - think 401(k), but for health insurance. Employers set a budget, employees get a personal allowance, and Zorro's decision-support engine helps each person pick an individual plan that actually fits their doctors, medications, and wallet. The platform serves employers, employees, and the brokers who sell to them, and clients have averaged over 20% premium savings versus traditional group coverage.
Roy Mill is the Co-Founder and CEO of Joshu, a no-code insurance product platform that lets carriers and MGAs launch digital distribution channels in weeks rather than years. A Stanford PhD economist who pivoted into product, he spent years at Ancestry and At-Bay before founding Joshu in 2020. The company has raised $11.7M in total funding and was named to the InsurTech100 list in 2024.
Vas Bhandarkar is the co-founder and CEO of ScoreData Corporation, a Palo Alto machine-learning company whose ScoreFast platform builds and monitors predictive models for insurers, banks, and call centers. A serial entrepreneur, he was an early employee at two AI companies that IPO'd on Nasdaq (Remedy and Selectica), ran Unimobile through a sale to Electronics for Imaging, and sat on the board of GlobalLogic during a 30x revenue run. He trained as a physicist at IIT Bombay before turning to computer science and decades of company-building in Silicon Valley.
Will Young is the co-founder and CEO of Sana, an Austin-based tech-enabled health plan that aims to cut small-business health insurance costs by up to 30%. A Stanford and Harvard Business School graduate who passed through Google and Justworks before starting a company in an industry he had no background in, Young bet that being an outsider was the advantage. Sana launched in 2018, went fully remote from day one against investor advice, and by its $60M Series B in 2022 had raised roughly $107M total while operating across eight states.
James Jiang is the cofounder and CEO of Spark, a New York company building the technology and back-office services that independent Medicare brokers use to run their businesses. A Yale graduate who started as a global technology investor and then cofounded the in-home senior care company Roster Health, he bet that the future of Medicare belongs to local independent agents rather than call centers or private-equity roll-ups. Under his lead, Spark raised a $25M Series B in 2024 and processed roughly 250,000 enrollments across 10,000 agents in 2025.
Laura Speyer is the co-CEO of Catch, a benefits marketplace that helps America's self-employed and independent workers find and enroll in health, dental, and vision insurance. After Catch's original founders shut the company down in March 2023, Speyer and her former CLEAR colleague Alexa Irish bought it with their own money and relaunched it in time for the November 2023 open enrollment. A Yale-trained dealmaker who came up through KKR and led corporate development and growth at CLEAR, Speyer pitches Catch as a 'personalized HR department' for the roughly 60 million Americans who work without an employer's safety net.
Paul Monasterio is the CEO and co-founder of Kalepa, a New York AI company building decision-support software for commercial insurance underwriters. A Venezuelan-born nuclear physicist with a PhD from MIT, he traded particle research for big-data analytics at Applied Predictive Technologies (acquired by Mastercard for $600M) and Facebook before launching Kalepa in 2018. Its Copilot platform helps underwriters 'bind with confidence,' and the company raised a $14M Series A from Inspired Capital in 2021.
EIS Ltd (EIS Group) is a San Francisco-based insurance software company that builds cloud-native core systems for ambitious insurers. Its flagship EIS OneSuite platform - now infused with agentic AI through CoreGentic - handles policy, billing, claims and customer management across property & casualty, life, annuity and benefits lines, replacing the rigid legacy mainframes that have slowed the industry for decades.
Alec Miloslavsky is the Founder and CEO of EIS Ltd (EIS Group), a San Francisco-based cloud-native digital insurance platform serving major insurers including Aflac, Allstate, Liberty Mutual, and Nationwide. Born in Ukraine and relocating to the US at age 17, he co-founded Genesys Telecommunications in 1990 - a contact center technology company he helped grow to a $1.9 billion acquisition by Alcatel-Lucent. He then co-founded Exigen Services, growing it past $70M in revenue, before pivoting to insurance tech by founding EIS Group in 2008. Under his leadership, EIS has raised over $224M in funding and built a modular, API-first core platform used across five insurance segments globally.
Angle Health is a San Francisco-based, AI-native health insurance platform for small and mid-sized employers. Founded in 2019 by ex-Palantir engineers, it combines carrier, third-party administrator, and underwriting functions into one stack, letting brokers quote level-funded plans in minutes and giving members a mobile-first care experience.
At-Bay is an InsurSec company that sells cyber insurance alongside the security tools, monitoring, and incident response needed to actually prevent claims. By bundling underwriting with active risk management, the company has positioned itself as both insurer and security partner for small and mid-sized businesses.
Cowbell is a Pleasanton-based insurtech that sells adaptive cyber insurance to small and mid-sized businesses, using an AI-driven continuous underwriting platform that scores cyber risk and can issue a policy in under five minutes.
Federato is an AI-native insurance platform built around a framework it calls RiskOps - software that connects portfolio strategy to the day-to-day decisions underwriters make on individual policies. Founded in 2020 by Stanford researchers Will Ross and William Steenbergen, the company sells to property-and-casualty carriers, MGAs and mutuals, and reports customers regularly see a 90% improvement in time-to-quote and a 3x lift in profitable business bound. In November 2025 it raised a $100M Series D led by Goldman Sachs Alternatives.
Glow is a San Francisco insurtech rebuilding workers' compensation insurance for small businesses. Founded in 2018 by Samad Wahedi, the company combines a digital platform, payroll-integrated pay-as-you-go billing, and a concierge claims experience to give the people who run America's small businesses coverage that's faster to buy, fairer to price, and friendlier to use.
Hourly is a Palo Alto-based fintech platform that combines payroll, workers' compensation insurance, and time tracking into a single mobile-first system built for small businesses with hourly workers. Its pay-as-you-go workers' comp model calculates premiums against actual wages in real time, eliminating year-end audits and helping employers avoid overpaying. Founded in 2018 by Tom Sagi, Shay Litvak, and Amir Faintuch, the company raised $39M+ and serves 500+ businesses across construction, manufacturing, transportation, and similar industries. In July 2025, Hourly was acquired by Israeli insurtech WeSure in a deal valued at approximately $168M.
InfrasAI (formerly iLife Technologies) is a Sunnyvale-based AI infrastructure company that builds the plumbing behind modern insurance distribution. Their headless API platform lets insurance carriers connect to any distributor channel - agents, brokers, IMOs - without rebuilding integrations from scratch each time. The core bet: use agentic AI to auto-generate workflows from natural language, collapsing integration timelines from 24 weeks to about 2. Customers include Transamerica and Guardian Insurance. Backed by Foundation Capital, Brewer Lane Ventures, SCOR, and others, InfrasAI has raised $28M total.
Ladder is a Palo Alto-based digital life insurance company that lets people apply for fully-underwritten term life coverage online in minutes, with the ability to ladder coverage up or down as life changes. Founded in 2015, it became the first fully digital life insurance carrier in 2021 after launching its own underwriting entity, Ladder Life Insurance Company.
Nirvana Insurance is a San Francisco-based, AI-native commercial trucking insurer that combines real-time telematics data with proprietary risk models to price, underwrite, and manage fleet insurance policies. Founded in 2021 by ex-Samsara, MIT, and Wharton operators, the company turns the data trucks already generate into safer roads, cheaper premiums, and faster claims.
Akash Agarwal is the Founder and CEO of Pibit.AI, a Y Combinator-backed insurtech company revolutionizing commercial insurance underwriting through AI. Building on a childhood watching his father toil as an insurance agent buried in paperwork, Akash set out to automate the most labor-intensive parts of underwriting. Pibit.AI's CURE platform - Centralized Underwriting Risk Environment - processes loss runs, submission documents, and risk data at machine speed, helping insurers cut underwriting cycle times by up to 85% and improve loss ratios by up to 700 basis points. After raising a $7M Series A led by Stellaris Venture Partners in November 2025, with participation from Y Combinator and Arali Ventures, the company is scaling its AI models and data partnerships to reshape how the $1T+ P&C insurance industry makes risk decisions.
AJ Altman is the founder and CEO of Hover, a San Francisco-based proptech company that turns smartphone photos into precise 3D models of homes - used by contractors, insurers, and homeowners to measure, design, and estimate renovation projects. A U.S. Marine Corps veteran and computer engineer by training, Altman left Intel at 29 to serve as an infantry officer before channeling military-grade geospatial mapping technology into a commercial platform that has raised over $146M and reached a $490M post-money valuation. Hover's platform now replaces five separate contractor apps and is backed by some of the country's largest insurance carriers.
Anirban Gangopadhyay is the co-founder and CTO of Angle Health, an AI-native health insurance platform serving small and mid-sized businesses across 44 U.S. states. A Columbia University computer scientist and former Palantir machine learning engineer, he previously served as a Stokes Scholar at the U.S. Department of Defense and co-founded Zircon Technologies - an AI-enabled clinical trial recruitment startup that was acquired - before building Angle Health through Y Combinator's W20 batch. Angle Health raised $134 million in a December 2025 Series B and has grown revenue 26x since its Series A, with a mission to redesign healthcare delivery through AI-first technology.
Art Agrawal (full name Abhas 'Art' Agrawal) is a serial entrepreneur and Co-Founder & CEO of Jerry (jerry.ai), an AI-powered car ownership super app based in Palo Alto, California. A TechCrunch Disrupt 2012 winner with his prior startup YourMechanic, Art has spent over a decade attacking the friction-laden world of car ownership - from on-demand repairs to insurance comparison and auto loan refinancing. Jerry has raised $330M+, reached profitability in 2024, and serves over 4 million customers, saving them an average of $800/year on car insurance.
Bill Liu is the Co-Founder and COO of Seel, the San Francisco-based company that invented Return Assurance — AI-powered insurance that lets shoppers add a refund window to final-sale purchases at checkout. Liu co-founded the company (originally called Kover.ai) in 2019 with CEO Zack Peng after completing the Techstars MetLife Digital Accelerator. He oversees team-building and go-to-market strategy for a platform now trusted by 5,000+ merchants, protecting 24 million+ orders and serving 2 million+ monthly shoppers. Seel has raised $29M+ in total funding including a Series B in May 2025 and was named to CB Insights' AI100 list of the world's most promising AI startups in 2023.
Bobby Touran is the Co-Founder and CEO of Rainbow, a San Francisco-based insurtech company building vertically specialized small business insurance products starting with restaurants. With over 15 years spanning insurance and software development, Touran previously co-founded Pathpoint, a digital E&S brokerage. At Rainbow, he is pioneering continuous underwriting - using real-time data like POS systems and online reviews to dynamically price risk - and has raised $20 million total to expand specialized coverage across multiple business verticals.