Microsoft's AI Ally: Reach Security Fixes the E3/E5 Security Gap

SAN FRANCISCO, CA – December 02, 2025 – In a move that signals a significant shift in enterprise cybersecurity strategy, AI-native security firm Reach Security has been accepted into the exclusive Microsoft for Startups Pegasus Program. While such announcements are common in Silicon Valley, this partnership goes beyond typical corporate collaboration. It represents a targeted effort by Microsoft to solve a persistent, multi-billion-dollar problem for its largest customers: the cavernous gap between investing in powerful security tools and actually realizing their full protective value.

The Billion-Dollar Blind Spot in Enterprise Security

For years, Chief Information Security Officers (CISOs) have been in an arms race, investing heavily in sophisticated security suites to defend against an ever-evolving threat landscape. Microsoft’s E3 and E5 licenses are a cornerstone of this strategy for countless organizations, offering a comprehensive arsenal of tools covering everything from endpoint protection and identity management to email security and data governance.

The paradox, however, is that many of these powerful capabilities remain underutilized. Industry analysis reveals that most organizations activate less than half of the security features included in their licenses. The reasons are numerous: overwhelming complexity, a shortage of specialized talent, and the constant, subtle erosion of security posture known as "configuration drift." Initial setups, however perfect, degrade over time due to system updates, human error, and changing business needs, creating silent vulnerabilities that attackers are quick to exploit.

This leaves security teams in a frustrating position: they are data-rich but insight-poor, buried under a mountain of alerts from siloed tools without a clear path to prioritized, effective action. The result is wasted investment, a fragmented security stack, and a false sense of security that masks significant exposure.

Enter the Agent: AI That Takes Proactive Action

This is the challenge Reach Security was built to address. The company is pioneering the use of agentic AI—a leap beyond the predictive models and generative assistants that have recently dominated the AI conversation. Unlike traditional AI that simply identifies potential issues or suggests fixes, Reach’s AI agents are designed to act autonomously. They perceive the security environment, reason through complex data, formulate a plan, and execute remediation with minimal human intervention.

“We’re redefining how companies close the gap between security investment and outcomes, using agentic AI to operationalize Microsoft’s E3 and E5 capabilities and help teams move from awareness to action across their security environment,” said Garrett Hamilton, CEO and co-founder of Reach Security.

The platform functions as an AI-native assistant that translates high-level security intent into concrete enforcement. It continuously scours an organization's Microsoft security stack, identifying misconfigurations, underutilized features, and policy drift across Microsoft Defender, Entra ID, and Purview. But its work doesn't stop at identification. The AI agents then prioritize these gaps based on real-world exposure and automate the remediation process, effectively acting as a tireless virtual teammate for overburdened security teams. Crucially, it simulates the business impact of any proposed change before deployment, ensuring that security hardening doesn't accidentally disrupt productivity—a common fear that often leads to inaction.

A Strategic Symbiosis Backed by Microsoft

Reach Security's acceptance into the Pegasus Program is the culmination of a deepening relationship with Microsoft. The startup is not just any applicant; it’s an invite-only participant in a program designed for high-growth B2B companies with proven market fit. This initiative provides more than just the up to $350,000 in Azure, GitHub, and LinkedIn credits; it offers deep go-to-market support, co-selling opportunities with Microsoft's own sales force, and direct access to enterprise customers.

"We welcome Reach Security to the Microsoft for Startups Pegasus Program," noted Tom Davis, a Partner at Microsoft for Startups. "Through Pegasus, startups can build fast, scale smart, and sell more by tapping into the full power of Azure and the Microsoft ecosystem."

This strategic embrace was foreshadowed by a recent $10 million strategic investment in Reach Security led by M12, Microsoft’s venture fund. That investment was a clear signal of Microsoft's validation of agentic AI and its recognition that solutions like Reach are essential for customers to unlock the full value of their Microsoft security investments. By backing and promoting a company that makes its own flagship products more effective, Microsoft is playing a savvy long game, ensuring customer success and stickiness within its ecosystem.

From Security Awareness to Measurable Enforcement

The practical implication for business leaders is a fundamental shift from a reactive security posture to a proactive, outcome-driven one. The collaboration aims to transform how enterprises manage their Microsoft security suites, moving them from simply being aware of vulnerabilities to actively enforcing a stronger, more resilient security posture.

By automating the analysis, prioritization, and remediation cycle, Reach’s agentic AI promises to deliver measurable exposure reduction across the most critical attack vectors: identity, endpoints, email, and network controls. This frees human security analysts from the monotonous work of chasing down misconfigurations and allows them to focus on higher-value tasks like threat hunting and strategic defense planning.

This model directly addresses the board-level demand for demonstrable return on security investment. Instead of pointing to a long list of purchased software licenses, CISOs can now present clear metrics on risk reduction, closed security gaps, and optimized tool utilization. It unifies a fragmented set of powerful but disconnected controls into a cohesive, intelligent, and self-tuning defense system. As cybercriminals increasingly leverage AI for their attacks, this partnership represents a crucial step in deploying AI for defense, empowering organizations to strengthen their posture and protect their assets at machine speed.