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Caddi co-founders Aditya Sastry, left, and Alejandro Castellano. (Caddi Photo)
A Seattle startup hatched out of AI2 Incubator is emerging from stealth today, announcing a $5 million seed round to fuel its goal of automating basic business operations with generative AI.
Caddi is developing “automation by demonstration” technology, allowing users to create screen recordings with audio that serve as AI training videos for tasks such as customer onboarding, email management, document organization, data entry and invoicing. The system then converts these recordings into automated workflows, effectively creating a virtual employee.
Caddi’s initial focus is on the legal and financial sectors.
The startup’s name is inspired by the role of a golf caddie, who handles the tedious, behind-the-scenes tasks so players can focus on the game itself.
“You are the expert in your topic,” co-founder and CEO Alejandro Castellano told GeekWire. “Let us help you run all the admin, back-office work.”
Castellano launched Caddi in August with co-founder and Chief Technology Officer Aditya Sastry.
Both are serial entrepreneurs. Castellano, originally from Peru, spent five years managing a portfolio of companies and investments at a financial firm before earning a master’s degree in engineering from Cornell University. He then joined AI2 Incubator as an entrepreneur-in-residence, eager to build software. The incubator was once part of the Allen Institute for Artificial Intelligence, breaking off in 2022.
“They were AI before AI was cool,” Castellano said. “So they actually knew how to build companies in the space.”
Sastry is a data science specialist who has led engineering teams at multiple startups and was the director of engineering at Denver-based AgentSync, an insurance tech giant.
The team also includes founding engineer Dallas Slaughter. The plan is to grow to 15 employees over the next year.
Caddi’s seed round was led by Ubiquity Ventures, with participation from Seattle-based Founders’ Co-op and AI2 Incubator.
Sunil Nagaraj, a general partner at Ubiquity Ventures, is joining Caddi’s board. Nagaraj’s previous investments include Auth0, a Seattle startup that was acquired by Okta for $6.5 billion.
Caddi tested its tech with pilot users in late 2024 and is now onboarding new customers. The goal is to do an open launch later this year, making the automation tools available for customers to use without the direct support of the Caddi team. The startup plans to offer its platform as a subscription service.
The generative AI automation space is rapidly expanding, and Caddi faces competition from multiple players.
Companies such as Zapier and Make are offering no-code solutions, but users must still understand technical concepts like triggers, actions and data mapping, Castellano said. Caddi customers don’t need that expertise.
Other competitors, including UiPath, Automation Anywhere and OpenAI’s Operator, automate workflows by mimicking a human user’s actions, clicking and typing. This approach can be unreliable when interfaces change and poses risks in regulated industries, Castellano said.
Caddi instead uses AI to analyze a screen recording to understand the intent behind user’s actions. It then generates code that interacts directly with application APIs to build the automated process, reducing the chances of errors and compliance risks.
As lawyers, accountants, financial planners, and other professionals face increasing pressure to improve efficiency and cut costs with AI, worries remain about the accuracy and reliability of automation tools. Caddi aims to address those concerns.
“We’re way more reliable, we’re way more cost effective,” Castellano said. “And there’s not any hallucination or regulatory risk.”
