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The Venture Codex

Glasswing Ventures

275 Newbury Street, 3rd Floor, Boston, Massachusetts, 02116, United States

Overview

Glasswing Ventures is an early-stage VC firm investing in the next generation of AI and frontier technology startups enabling the rise of the intelligent enterprise. The firm is laser-focused on funding exceptional entrepreneurs who are leading the AI revolution, capitalizing on the intellectual might and talent from the premier academic institutions on the East Coast, and fostering growth for its ecosystem. Glasswing Ventures funds visionary entrepreneurs harnessing the power of AI and frontier technologies to transform markets and revolutionize industries. Glasswing Ventures was founded in 2016 and is headquartered in Boston, Massachusetts, USA.

Total investments
61
Lead investments
25
Investments · 12mo
10
Active investors
8

Sector focus

  • Artificial Intelligence (AI)
  • Cyber Security
  • Enterprise
  • Enterprise Software
  • Security
  • Supply Chain Management
  • Venture Capital
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Investment portfolio

  • Samepage.ai

    Participated · Equity · Jun 2026

    Samepage.ai’s flagship product, Samepage Signals, connects natively to more than 35 product, customer, and business data sources (including Jira, Linear, Productboard, Slack, Notion, Gong, and Salesforce) to build a dynamic profile of each product leader and proactively surface the most relevant information and insights. Key capabilities include automated connection to core tools, dynamic user profiling, and proactive surfacing of feature ideas, competitor developments, and shipment risk. The product was tested in beta with hundreds of product leaders before the public launch. The founding team—Sahil Jain, Jason Wu, and Paul Wicker—previously built AdStage and emphasize solving operator pain points around information overload and cross-functional misalignment. With the $4.85M raise, Samepage plans to continue product development and drive broader adoption of Signals as it commercializes the offering.

  • Enlaye

    Led · Seed · Jun 2026

    Enlaye provides a platform that aggregates documents and data — contracts, technical documents, schedules, site reports and project histories — to detect correlations, signals and contextualized risk analyses for construction, real estate and infrastructure projects. The company uses multimodal AI models and Graph Neural Networks to link dispersed information and surface actionable knowledge for operational teams rather than replace subject-matter experts. Its platform is already deployed on over $17 billion of projects across the U.S., Canada and Europe and is used by several entities within the VINCI group, benefiting from Leonard's support since 2025. Enlaye's stated objective is to build a "memory of risk" for construction organizations so lessons from past projects can reduce delays, disputes and cost overruns. Financially, the company recently raised a €4.25 million Seed round to accelerate product development.

  • Flux

    Participated · Equity · Jun 2026

    Flux provides a code-first engineering intelligence platform that analyzes source code and code changes to reveal what engineering teams are actually building, surface risk and technical debt, and connect engineering activity to business outcomes. The company positions its platform as a system of record for engineering leaders to understand value from AI, shifts in work types, and emerging issues before they become incidents. Flux highlighted a customer example, Cobalt, where its work-type charts quantified a shift from maintenance to feature delivery that informed finance decisions. CEO and founder Ted Julian framed the product as enabling leaders to lean into AI with visibility tied to the code itself. Flux plans to use the newly raised $5 million to deepen AI analysis, expand capabilities around cost, quality, security and technical debt, and to grow its go-to-market and engineering teams. The company announced the raise from its Boston location.

  • Sigma Automate

    Led · Equity · Apr 2026

    Sigma Automate provides a visual, no-code platform designed to simplify automation for hybrid enterprise IT environments spanning on-premises systems, cloud infrastructure, and virtual desktops. The platform includes no-code orchestration, autonomous self-healing, patch management, and compliance monitoring to reduce downtime, strengthen security, and lower operational burden. Sigma positions its product to enable rapid deployment and automation in minutes without requiring specialized DevOps coding expertise. The company has launched with early revenue traction and deployments at customers such as SiteOne Landscape Supply, which uses the platform to manage thousands of virtual machines across multiple data centers. The team is led by CEO Richard Shaaya, CTO Ben Barbour, and COO Greg Arnette, who have prior leadership experience in enterprise IT and infrastructure software. Sigma reports customer adoption across retail, logistics, and healthcare as it scales commercially after emerging from stealth.

  • Krane

    Led · Seed · Mar 2026

    Krane is an AI-native construction supply chain management platform led by founder and CEO Eshan Jayamanne and based in San Francisco, CA. Its product automates materials workflows by assigning AI "team members" to tasks such as turning specs into submittal and procurement logs, connecting schedules and procurement data, following up with trade partners, creating submittal templates and QCs, automating delivery scheduling, and controlling procurement from quote comparison to delivery. The company recently added Theo to expand the platform’s capabilities to owners and subcontractors by helping teams control procurement and RFP processes. Krane integrates with construction systems including Autodesk, Procore, Microsoft Project, CMiC, Microsoft SharePoint, Trimble Viewpoint, and Oracle Primavera P6. It currently manages $15 billion in active projects across the U.S. and Canada spanning data centers, K–12, and biotech. The company plans to use the new seed funding to accelerate its product roadmap and expand enterprise deployments.

Team