Cybersecurity Startup Breaks Into Enterprise with AI Outbound

The Challenge

A cybersecurity startup with a strong product and several mid-market customers needed to break into the enterprise segment. Their co-founder had been handling sales solo, booking 3-5 meetings per month through personal network and conference attendance. They needed systematic outbound to reach CISOs and security leaders at companies they had no existing relationship with, but their first SDR hire had quit after 4 months with minimal results.

The Solution

SentByTed was configured to target Director of Security and CISO-level contacts at companies in regulated industries (financial services, healthcare, government contractors) with 500-5,000 employees. Ted enriched each prospect with technology stack data, compliance requirements (SOC 2, HIPAA, FedRAMP), and recent security incidents in their vertical. Outreach was technical and specific — referencing the prospect's likely compliance challenges and positioning the product as addressing a specific gap in their stack.

Results

• 22 meetings per month with security leaders at target companies
• 4.1% reply rate (exceptional for cybersecurity buyer personas)
• 3 enterprise contracts closed in the first quarter ($380K combined ACV)
• Pipeline grew from $200K to $1.8M in 90 days
• Co-founder freed from prospecting to focus on product and closing

Timeline: Live within 48 hours. First enterprise meeting booked on day 6.