
He made Forbes 30 Under 30 for a company he then threw away. The second version of Glimpse - AI that fights retail's most boring, most expensive fee - just raised $35 million.
10x Dental is a Y Combinator (W25) startup that builds AI sales teams for dental practices. It plugs into a practice's patient database, finds overdue recalls, lapsed patients, and unscheduled treatment plans, then calls and texts those patients automatically to book them back into the chair - recovering revenue that would otherwise slip through the cracks.
Aegis is a San Francisco healthtech startup (YC X25) that automates the insurance denial appeals process for healthcare providers, hospitals, and medical billing groups. Its AI detects denied claims, pulls supporting records from EHRs and clearinghouses, drafts policy-specific appeal letters, and submits and tracks them through payer portals - helping providers recover revenue that would otherwise go unclaimed because appeals are too slow and costly to file by hand.
Boom AI is a San Francisco-based Y Combinator (F25) startup building an AI workforce that talks to a company's customers across SMS, email, WhatsApp, Instagram, and phone, learns what they need, and acts on it - collecting overdue payments, winning back churned users, driving sales, and onboarding people. Founded in 2025 by the team that built Atrato (YC W21), it aims to deliver the output of a full customer team without the headcount.
Third Chair is an AI-native IP enforcement and licensing platform that helps rightsholders find who is using their content, trademarks, and likeness without permission and turn that unauthorized use into revenue. Backed by Y Combinator (X25) and FundersClub with $2.3M raised, it pairs AI agents that monitor, investigate, and draft demand letters with an on-demand network of lawyers. Customers - including Universal Music Group and much of the recorded-music industry - used the product to generate more than $1M in revenue in the last six months of 2025.
Amperos Health is a New York-based healthcare technology company building agentic AI that automates insurance denial management and revenue recovery for medical providers. Its AI biller, Amanda, works inside providers' existing billing systems to follow up on claims, place calls to payors, file appeals, and collect on denied and outstanding claims. Amperos serves more than 3,000 clinical locations across all 50 states and supports roughly $700 million in annual recovered revenue across 500,000+ claims. The company raised a $16M Series A led by Bessemer Venture Partners in April 2026, bringing total funding to about $20.2M.
Glimpse is an AI-native platform that automates deduction management for consumer packaged goods (CPG) brands. Its AI agents log into retailer portals, gather scattered documents, classify and validate deductions against internal data like promotion calendars and supply-chain records, then file disputes and recover cash that brands would otherwise write off. Founded in 2024 by three Purdue classmates after pivoting from an Airbnb product-placement startup, Glimpse works with 200+ brands and retail partners including Suave, Chapstick and Lemon Perfect, and raised a $35M Series A led by Andreessen Horowitz in March 2026.
Joyful Health is a New York-based health-tech company building AI-powered financial infrastructure for healthcare revenue. Its platform connects fragmented revenue cycle systems - EHRs, billing software, clearinghouses, payer portals, and bank deposits - into a single structured view of every claim's lifecycle, then pairs AI with experienced revenue cycle operators to investigate denials, file appeals, and recover unpaid and underpaid insurance claims. The company targets the roughly $125 billion U.S. providers lose to denied and underpaid claims each year and charges on a performance basis tied to recovered revenue.
Skit.ai is a New York-based conversational AI company that automates debt collection and accounts receivable operations for banks, agencies, fintechs, healthcare systems, and utilities. Founded in 2016 as Vernacular.ai and rebranded to Skit in 2021, it runs a generative-AI-powered platform of voice, SMS, email, and chat assistants plus a Collection Intelligence Platform and an ecosystem of specialized AI agents that negotiate payments, capture dispositions, and enforce federal and state collection compliance at scale.
Eliana Berger is the co-founder and CEO of Joyful Health, a New York startup building AI-powered financial infrastructure for healthcare providers. The company focuses on the hardest part of the revenue cycle - chasing down denied and unpaid insurance claims - and works on performance-based pricing, getting paid only when it recovers money for clients. In April 2026, Joyful Health raised a $17M Series A led by CRV, bringing total funding to $22M. Berger's path to the problem was personal: she grew up watching her mother and grandmother run a therapy practice and struggle to understand what had been paid and what was still owed.
Gravy is an Atlanta-area fintech that recovers failed subscription payments for recurring-revenue businesses. Instead of leaning only on automated dunning software, Gravy pairs workflow automation with U.S.-based retention specialists who personally reach out to customers whose cards declined - by email, text and sometimes a live agent. Founded in 2017 by Casey Graham and Renee Weber, the company says it has returned more than $500 million to hundreds of clients and lifts recovery rates from the industry-typical ~15% toward 80%.
Sticky.io is a San Francisco-based revenue optimization platform for high-volume subscription and ecommerce brands. Built on an intelligent payments engine, it pairs a headless CRM, a conversion-focused checkout and funnel builder, AI-driven payment recovery, and orchestration across 160+ gateways. The platform supports roughly 72 million subscriptions and processes more than $12 billion in transactions annually, helping merchants reduce silent churn and recoup failed payments.
Fintary is an AI-powered revenue and commission operations platform built for insurance brokerages, carriers, and wealth firms. It automates the end-to-end commission lifecycle - data extraction, reconciliation, calculations, splits, overrides, bonuses, and payouts - while giving agencies real-time visibility into profitability by line, carrier, product, and producer. Founded in 2021 by former agency owner Qiyun Cai, the company turns the spreadsheet-heavy back office of insurance distribution into a source of growth.
Brian Bogosian is President, CEO, and Chairman of Sticky.io, a San Francisco-based headless CRM and subscription payments platform that processes over $12 billion annually and powers 72 million+ subscriptions. A veteran technology executive, he previously led Good Technology (formerly Visto) as Chairman, President & CEO for a decade, growing it to become the industry's first mobile enterprise unicorn valued at $1.25 billion with 500+ employees in 10 countries. He founded Salt Technology and acquired LimeLight CRM - which he rebranded as Sticky.io in 2020 - to build a comprehensive payment orchestration and ecommerce retention platform backed by $90 million in debt financing from Goldman Sachs Asset Management and others.