Matt McIlwain
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.
Apptio Co-founders Sunny Gupta and Kurt Shintaffer Launch Thira, Raise $21M Seed Led by Madrona to Build Autonomous IT Support Agents
Apptio co-founders Sunny Gupta and Kurt Shintaffer launched Bellevue-based enterprise AI startup Thira to build autonomous agents for IT support and back-office work, and raised $21 million in seed funding led by Madrona. Thira will integrate with tools like ServiceNow, Jira Service Management and identity/device-management systems, with plans to expand into finance and HR amid competition from companies such as ServiceNow (Moveworks), Aisera, Rezolve.ai, and Serval.
Thira Secures $21 Million Seed Funding to Automate Enterprise Back-Office Workflows with AI
Thira, founded by Apptio co-founders in 2026, has raised $21 million in a seed round led by Madrona to develop an AI-native platform that automates complex enterprise back-office workflows while ensuring security and compliance.
Thira Secures $21M Seed Funding Led by Madrona to Develop AI-Driven Self-Running Enterprise Back-Office
Thira, founded by Apptio co-founders Sunny Gupta and Kurt Shintaffer, raised $21 million in a seed round led by Madrona to develop a secure, self-learning AI system aimed at automating enterprise back-office IT processes. The funding round also includes participation from FUSE and prominent advisors, with key industry veterans joining the founding team.
By Matt
See all 6AGI 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…
Organizations
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Thira Director 2026–present · current
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Exa Investor 2026–present · current
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Thira Board Member 2026–present · current
Education
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Harvard Business School Master of Business Administration (MBA) · 1990–1992
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Dartmouth College Bachelor's degree, Government with economics · 1983–1987
