Test Flight: Glasswing Ventures AI Hackathon

Test Flight is a two-day, in-person AI hackathon hosted by Glasswing Ventures at 275 Newbury Street in Boston on September 26 and 27, 2026. One weekend, and $300,000 in compute credits on the line for the team that wins.

The brief is Enterprise-Ready AI. Teams build AI-native solutions to problems enterprises actually have, not AI features bolted onto existing workflows. What gets rewarded is a working product demoed live, with a credible path to deployment and a measurable return.

Judging runs on four criteria. Customer Problem: does this solve a business challenge someone would pay to fix. Business Case: is there a clear adoption rationale with measurable outcomes. Operational Fit: could an enterprise realistically integrate and run this. AI Differentiation: is the AI load-bearing, and is there a data or model advantage behind it.

Compute and engineering support are provided throughout the weekend, backed by AWS, Microsoft Azure, and TensorWave. Meals are covered both days.

Format: Saturday opens with registration and breakfast at 9:30 AM, welcome remarks at 10:00, team formation and compute setup at 10:30, and building from 11:30 AM until 8:00 PM. Sunday resumes at 9:30 AM, with a hard code freeze at 2:00 PM, team presentations from 2:00 to 4:30, and the awards ceremony at 4:30.

Who should apply: technical builders, individually or in teams of up to four. Solo applicants and partial teams are matched with other qualified builders. Admission is by application and reviewed on a rolling basis, so applying early matters. Applications close September 19, 2026. Free to participate.

Glasswing Ventures is a Boston-based venture firm with over $450M in AUM, investing in AI and frontier-technology companies at the earliest stages.