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Sat, Jul 18, 2026 · 17 stories · Confirmed · Subscribe
TechBusiness

Apptio's Founders Return With Thira, Raising $21 Million From Madrona

Sunny Gupta and Kurt Shintaffer already sold iConclude to Opsware and Apptio to IBM for $4.6 billion before teaming again with Madrona.

  • Thira builds an agentic system of execution to run enterprise IT support automatically.
  • Ten lighthouse partners are already shaping the product months after its launch.
  • Madrona partner Matt McIlwain calls it the biggest opportunity the two have pursued.

Why it matters: A venture firm backing the same founders again is betting on relationships, not the pitch.

Madrona (Matt McIlwain), "Why We Invested in Thira" ↗ · Jul 18, 20267/18/26 · ✓ Checked✓ Check