gradient-ventures
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Arrows Ripped Out a Third of Its Product on Purpose
Two friends who lived two blocks apart built an onboarding tool, then bet the whole thing on HubSpot - cutting a third of the features to go deeper. It became one of the marketplace's most-installed apps.
FirstWork
FirstWork is a San Francisco-based, YC S24 enterprise AI company building autonomous agents that automate workforce operations for frontline and seasonal labor. Its platform handles document verification, credentialing, continuous compliance, and worker onboarding inside a company's existing systems, cutting time-to-hire and onboarding by up to 80%. Founded in 2024 by Vardhan Kapoor (ex-Remitly, Deliveroo) and Shubham Choudhary (ex-Deel, Rippling), FirstWork raised a $5M seed round led by Gradient and serves staffing, logistics, delivery, and care companies including Deel, Job&Talent, Relay, and Wonolo.
Arrow
Arrow is a New York-based healthcare technology company building an AI-powered operating system for revenue cycle management (RCM). Formerly known as Walnut and often described as 'Stripe for healthcare,' Arrow helps healthcare organizations reduce claim denials, accelerate collections, and run billing, claims, and payer communications from a single platform. Founded in 2020 by Roshan Patel and Yash Joshi, the company emerged from stealth in 2024 with $110M in Series A financing led by Gradient Ventures.
Roshan Patel
Roshan Patel is the co-founder and CEO of Arrow, a New York-based healthcare payments company (formerly Walnut) that uses AI to detect claim errors, accelerate reimbursement, and give revenue cycle teams real-time visibility into what payers are doing. He built the original company as a buy-now-pay-later product for medical bills after watching a family member's bills pile up, raised a $110 million Series A led by Gradient Ventures in 2022, then pivoted the business toward provider-side claims infrastructure and rebranded to Arrow in 2024.
Arva AI
Arva AI builds enterprise-grade AI agents that do the manual grunt work of financial crime compliance - screening, KYB/KYC onboarding, and transaction monitoring - for regulated banks and fintechs. Its agents autonomously resolve the majority of alerts and reviews (roughly 91% of screening alerts, 87% of KYB/KYC assessments, and 86% of transaction-monitoring alerts), cutting onboarding times from days to seconds and compliance operations spend by up to 80%. Founded in 2024 by Rhim Shah and Oli Wales and part of Y Combinator's Summer 2024 batch, the New York-based company raised a $3M seed round led by Google's Gradient Ventures in January 2025.
Cake
Cake is a New York-based startup that bundles the sprawling open-source AI stack into a single managed platform, so companies - especially in regulated industries like finance, insurance and healthcare - can deploy AI inside their own cloud without wiring together 100+ tools by hand. Founded in 2022 by Misha Herscu and Skyler Thomas and launched from stealth in December 2024 with a $13M seed led by Google's Gradient Ventures, Cake handles the integration, security, governance and cost-monitoring glue around open-source components like LangChain, Ray, MLflow and vector databases, all deployed inside a customer's own VPC so data never leaves.
Humata
Humata is an Austin-based AI company that lets people upload files and ask questions about them in plain English, returning answers with clickable citations that point back to the exact passage in the source document. Often described as 'ChatGPT for your files,' it targets professionals in legal, finance, healthcare, and research who need to extract insight from dense, unstructured documents without reading every page. Founded in 2022 by Cyrus Khajvandi and Dan Rasmuson, the company raised a $3.5M seed round in October 2023 led by Google's Gradient Ventures with participation from Cathie Wood's ARK Invest and M13.
Allen Wang
Allen Wang is the cofounder and CEO of Ditto, a swipe-free AI matchmaking service for college campuses that plans real, in-person dates over iMessage. He dropped out of UC Berkeley after starting the company with cofounder Eric Liu - reportedly to help a roommate find a girlfriend before graduation. By early 2026 Ditto had grown to roughly 42,000 students across University of California campuses and raised a $9.2 million seed round led by Peak XV Partners, with Gradient Ventures and others participating, on a bet that Gen Z wants fewer screens and more real dates.
Ana-Maria Constantin
Ana-Maria Constantin is the CEO and co-founder of Cascade AI, a Bellevue-based startup building agentic AI that automates the grind of HR and back-office operations. A Harvard dual major in computer science and astrophysics who left Romania after high school, she spent five-plus years as a software engineer at Microsoft writing code that touched millions of users on Azure before deciding HR - the function that touches more lives than any other in a company - was the perfect place to point machine learning. She raised a $5.45M-plus seed round led by Google's Gradient Ventures with AlleyCorp, was named GeekWire's Young Entrepreneur of the Year in 2024, and recognized as a 2025 Google Cloud Partner All-Star.
Cyrus Khajvandi
Cyrus Khajvandi is the co-founder and CEO of Humata, an Austin-based AI startup often described as 'ChatGPT for all your files.' A Stanford biology graduate and serial entrepreneur, he built Humata after struggling to keep up with scientific papers, turning that personal frustration into a tool that lets people ask questions of their documents and get cited, fact-checkable answers. The company launched in early 2023, grew to millions of users processing tens of millions of pages, and raised $3.5M led by Google's Gradient Ventures with ARK Invest and M13.
Misha Herscu
Misha Herscu is the co-founder and CEO of Cake, a New York based platform that bundles more than 100 open-source AI components into managed, production-ready infrastructure so mid-market teams get the control of a build with the ease of a buy. A Harvard physics graduate turned full-stack engineer, he previously founded the radiology AI marketplace EnvoyAI (McCoy Medical Technologies), which TeraRecon acquired in 2018. After running over 200 customer-discovery calls as an operator in residence at Primary Venture Partners, he started Cake in 2022 with CTO Skyler Thomas and raised a $13M seed round led by Google's Gradient in late 2024.
Rhim Shah
Rhim Shah is the co-founder and CEO of Arva AI, a Y Combinator and Google AI Fund-backed startup building auditable AI agents that automate financial crime compliance reviews for banks and fintechs. An Oxford engineering graduate who led the FinCrime product team at Revolut Business, he spent hundreds of hours shadowing compliance analysts before deciding the mundane, repetitive work of AML, KYB and KYC could be done faster and deeper by AI. Arva now automates as much as 80-92% of manual review work and counts leading UK and US banks among its customers.
Richard Meng
Richard Meng is the co-founder and CEO of Roe AI, a Y Combinator-backed (W24) startup building an AI-powered data warehouse that lets data teams query unstructured, multimodal data - documents, images, web pages, video - with plain SQL. A UC Berkeley CS and Statistics double major, he previously led generative AI engineering at Snowflake and worked on the Skills and Knowledge Graph products at LinkedIn before founding Roe AI in 2023 to solve a problem that nagged him for a decade: the 80% of enterprise data that never gets used because it isn't in neat rows and columns.