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Investing in Chief

We’re investing in Chief via Deepwater Venture Fund II because we believe Chief is building the leading tool for businesses to optimize operations.

Humans cannot synthesize and analyze the quantity of business data available to them; machines are far better equipped. Until now, however, machines have struggled to identify and communicate relevant business insights to human users. Chief is automating business operations analysis with proactive AI agents. Chief’s ultimate vision is to help promote AI agents from tools to partners to managers, and eventually to a company’s Chief of Staff.

Deepwater participated in Chief’s Seed round in late 2024. Co-investors include Dundee Venture Capital, York IE, and Upstream Ventures, along with several angel investors.

The advent of transformer models and LLMs unlocks a machine’s capability to ingest huge amounts of raw data, surface relevant insights with minimal guidance or prompting, and communicate recommendations proactively. Products and services like Chief will move the AI age from infrastructure buildout to value creation. Here’s how it works:

  • Chief creates a custom LLM for its business customers using data from sources like HubSpot, Salesforce, Zendesk, and Marketo.
  • Chief proactively surfaces an insight, provides direction, and helps assign and track the action, all using Slack, email, or another preferred communication medium.

Initially, Chief’s core customer is the RevOps team at B2B SaaS companies. RevOps combines the three functions closest to revenue: sales, marketing and customer success. This means that applications of Chief to RevOps functions have the greatest potential for bottom-line impact. Longer-term, Chief’s solution could have far-reaching use cases across multiple verticals, broadly addressing opportunities in a forecasted $1T addressable market for AI agents in the next decade.

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