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Andrew Dillon

Andrew Dillon

Founder and CEO driving product innovation with AI velocity

drewdil
San Francisco, California
Joined January 2025
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7.1K connections
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AI ML Founders
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Product GTM Leaders
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a16z Speedrun Founders
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Venture Capital Investors
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SaaS Enterprise Leaders
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a16z Investors Partners
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Summary

Andrew Dillon is a seasoned product leader and entrepreneur with a strong focus on emerging technologies, particularly Artificial Intelligence. He has consistently led product strategy, engineering, and business development across multiple companies, from startups like Brief and Mocksi to larger organizations like Microsoft and Yammer. His recent ventures are deeply embedded in the AI space, aiming to enhance product development workflows and provide AI agents with critical business context. linkedin+2
His expertise spans the entire product lifecycle, from initial concept and strategic planning to execution and market delivery. He is adept at building and leading product teams, understanding technical requirements, and translating business needs into effective solutions. His background as a Systems/Sales Engineer at Ingrian Networks and SAIC also highlights his capability in technical integration, customer relations, and driving sales. clarity+1
Andrew has a demonstrated ability to innovate and adapt, evident in his transitions from data protection to enterprise communication platforms, and now to AI-native product development. He has been involved in significant industry events, including the a16z speedrun accelerator and multiple Founders Network summits, indicating a continuous engagement with the startup ecosystem and a drive for pioneering new solutions. linkedin+1

Work

Education

Writing

Scaling Product Strategy

December 1, 2019

An article discussing the importance and methods of scaling product strategy, contributing to his expertise as a product leader.

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What Everyone Gets Wrong About Enterprise Communication

March 1, 2016

An article from 2016 analyzing different communication needs within enterprises (synchronous vs. asynchronous, internal vs. external) and arguing against a single, universal communication tool. Draws on his experience at Yammer and AnyPerk.

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Inside My AI-Powered Product Management Workflow

An article detailing his workflow for using AI tools like Cursor and Claude in product management, emphasizing the continued criticality of PM skills for achieving effective outcomes with AI coding agents. He outlines a structured approach involving PRDs, tech specs, and implementation plans, leveraging AI to create an 'agent swarm' for parallel development.

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