Defense in Depth Sales Follow Up Sequences: What Works Best in Cyber?
Oct 23, 2025
Alex Guilday, BISO at Royal Caribbean Group and a former cybersecurity salesperson, shares insights on effective sales strategies in cybersecurity. He discusses the importance of tailoring outreach to avoid saturating security professionals with generic messaging. With a dual perspective, Alex reflects on the necessity of building long-term relationships over transactional tactics. He highlights the value of trusted peer recommendations and emphasizes the significance of timing and touch frequency in sales sequences.
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Security Buyers Are Uniquely Saturated
- Security buyers are saturated with outreach so generic aggressive sequences often fail.
- Tailor approach to the target and adapt tactics for security audiences who expect technical value.
Target The Right Person And Build Relationships
- Do focus outreach on the right person and problem to avoid wasting touches.
- Do build relationships instead of annoying targets with transactional repetition.
From Door-To-Door To Drip Campaigns
- Alex Guilday recalled doing brutal drip campaigns early in his sales career and feeling guilty.
- He compared ignored emails to door-to-door rejection where people literally slammed doors on him.
