How My AskAI Secured Enterprise Trust and Accelerated Sales with Red Sentry
See how My AskAI used Red Sentry’s penetration testing to achieve enterprise-ready security, accelerate sales, and prove their security posture.
Case Study
Executive Summary
My AskAI, an AI-powered customer service platform, needed to move beyond checkbox compliance. After achieving SOC 2 Type 2 status, they partnered with Red Sentry to conduct a deep-dive penetration test. This engagement did more than just harden their security; it provided the "proof of security" required to close deals with security-conscious enterprise clients.
The Challenge: Beyond the SOC 2 Checkbox
Achieving SOC 2 Type 2 was a major milestone for My AskAI, but co-founder Mike knew that for enterprise customers, it was only the beginning.
As a platform handling sensitive data, including private user conversations and account information, the stakes were high. A single vulnerability could compromise customer business data or damage enterprise client trust. Because prospects were already requesting recent penetration testing (pentest) results, the sales cycle risked stalling without them. My AskAI needed a security partner who could:
Understand a No-Code Stack: Most legacy firms struggle with platforms built on Bubble.
Prioritize Pragmatism: They required a partner focused on high-risk routes rather than generic scans.
Deliver Proof: The goal was a formal Letter of Attestation and executive summary suitable for procurement and security review teams.
The Solution: A Partnership, Not Just a Product
After evaluating several providers who focused more on sales demos than technical empathy, My AskAI chose Red Sentry.
The Scope included:
External Pentesting: Mapping and probing the platform's internet-facing attack surface.
Web Application Testing: A deep dive into the core AI platform logic.
API Testing: Assessing the interfaces that connect My AskAI with its customers' systems.
What Red Sentry Found: Beyond Automated Scanning
Given the complexity of My AskAI’s no-code architecture, automated scanners alone would not provide meaningful coverage. Red Sentry’s engineers performed deep manual testing, which resulted in no critical or high-risk vulnerabilities. The assessment uncovered a limited number of medium and low-severity findings along with configuration hardening recommendations. All findings were manually validated to eliminate false positives and ensure the remediation guidance was actionable.
Key areas of discovery included:
Business Logic Flaws: Testing the unique ways My AskAI processes and stores user conversations to ensure no cross-tenant data exposure was possible.
API Security Gaps: Identifying specific interface vulnerabilities that could have been exploited to bypass standard UI controls.
Configuration Hardening: Surfacing advisory-level improvements for their external attack surface to align with enterprise-grade best practices that go beyond SOC 2 requirements.
For a platform undergoing its first-ever pentest, this was a highly successful outcome. While there were zero critical findings, the team gained enough actionable intelligence to significantly harden the platform against sophisticated attackers.
Remediation & Retesting: Fast Turnaround, Verified Results
The value of a pentest depends on the speed of the fix. Red Sentry provided a clear, documented roadmap for the My AskAI engineering team to resolve findings without ambiguity.
Guided Resolution: Each finding came with specific remediation steps tailored to the environment, removing the guesswork for developers.
Seamless Communication: All communication was managed through Red Sentry's platform, keeping the process organized and transparent.
Rapid Validation: Within days of submitting the fixes, Red Sentry’s team retested and validated that every identified issue had been successfully addressed.
The Impact: Turning Security into a Competitive Advantage
By proactively addressing security, My AskAI transformed a potential sales bottleneck into a value proposition. With a formal penetration test report and attestation in hand, they now have a concrete asset to share with enterprise leads who previously listed pentesting as a requirement.
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