Matt McIlwain

Matt McIlwain

Investor at Exa
Sea Island, Georgia, United States

Matt McIlwain currently serves as a board member at several companies, including A-Alpha Bio, Amperity, Axiom Math, Booster, and EdgeRunner AI. He has previously held board roles at Accolade, Inc. (which went public in 2021), Apptio (which went public in 2016), Farecast, and Isilon Systems (which went public in 2006), as well as serving as Vice President of Business Process at Genuine Parts Company.

AGI Needs Formal Reasoning. Carina Hong is Building it at Axiom.

There's a theorem being tested about how AI reaches general intelligence. Carina Hong's answer: through mathematics. Carina is the founder of Axiom, and in less than a year of building, her team's AI has scored a perfect 120/120 on the Putnam mathematical competition — a test where more than 50% of brilliant undergraduates score zero. More concretely, Axiom Prover has reached 98.93% on a Lean software verification benchmark that leading alternatives solve at 11–12%. In this conversation with Matt McIlwain, Carina explains her central thesis: that math and code are the two pillars of the digital world, and that any…

How to Sell AI Into the Enterprise: Pilots, Pricing, and Closing 12-Month Deals

What does it really take to sell an AI-native product into the Fortune 500? In this episode of Founded & Funded, Madrona Managing Director Matt McIlwain sits down with two founders deep in the trenches of enterprise AI adoption, Esha Joshi (Co-founder, Yoodli⁩) and Anup Chamrajnagar (Co-founder, Gradial.) Their companies are selling into some of the world's most complex organizations, like Google, SAP, Snowflake, Databricks, and more. And they break down what founders often underestimate about enterprise AI sales. They dive into: Why most AI pilots fail and how to prevent it The "three-legged stool" of enterprise sales How AI…

Read AI's David Shim on Making Meetings More Efficient With Intelligent Agents

In this episode, Madrona Managing Director Matt McIlwain hosts David Shim, founder and CEO of Read AI. These two have known each other for over two decades, having worked together at Farecast and then Placed, which David founded in 2011. They came together again in 2021, when David started Read AI, which delivers AI solutions that make meetings, emails, and messages more valuable to teams with AI-generated summaries, transcripts, and highlights. In this episode, David and Matt examine how leveraging emerging technologies, getting engagement from multiple members of your ecosystem in the early days, and learning your way into a…

NYSE's Lynn Martin on Capital Markets, IPOs, and the Role AI Is Playing in the Markets

In this week's episode of Founded & Funded, Madrona Managing Director Matt McIlwain hosts NYSE Group President Lynn Martin ahead of our Intelligent Applications Summit on October 10th and 11th. Lynn will be speaking at the Summit, but we thought it would be great to have her on the show to talk more about her background, the NYSE, capital markets, IPOs, and, of course, the role data, AI, and large language models are playing in the markets and in companies broadly! This conversation couldn't come at a better time now that we're seeing a number of tech companies teeing up…

Acquired Hosts Ben and David on Getting Started at Madrona and Tom Alberg's Legacy

This week, we're excited to release a special live episode recorded during the community event portion of the Madrona 2023 annual meeting. Managing Director Matt McIlwain talks with Madrona Alumni and Acquired Podcast Hosts Ben Gilbert and David Rosenthal. The three reflect on Acquired episode No. 28, which dove into the Amazon IPO with the late Madrona Co-founder and original Amazon Board Member Tom Alberg, and the early days getting the show off the ground from the Madrona offices.

Top Tier's David York on Limited Partners, Market Conditions

In this episode of Founded and Funded, we stray a little from our typical format to answer some questions that often come up in discussions between founders and our investors. Madrona Managing Director Matt McILwain talks with one of our Limited Partners — or the partners of ours that are not the day-to-day investors — Top Tier Capital Partners Founder and Managing Director David York. They explore different kinds of funding mechanisms, the current market conditions, and a bit of a history between the two firms – more specifically, why this San Francisco-based firm decided to bet on Seattle and…

Organizations

See all 36
  • Thira logo
    Thira Director 2026–present · current
  • Exa Investor 2026–present · current
  • Thira Board Member 2026–present · current

Education

  • Harvard Business School Master of Business Administration (MBA) · 1990–1992
  • Dartmouth College Bachelor's degree, Government with economics · 1983–1987

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