Why Your First VP of Sales Will Fail (And What To Do Instead) – Eyal Worthalter, Multi-Time VP of Sales, Cybersecurity Startups

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Are you grappling with when, and who, to hire as your first sales leader in your cybersecurity startup? Wondering why sales leadership churn is so high, or if founders should keep selling longer? If you’ve debated hiring account executives versus a VP of Sales, and wrestled with investor pressure on scaling your sales team, this episode is for you.

In this conversation, we discuss: 

👉 The crucial distinction between sellers and sales leaders at different company stages
👉 Why timing, founder credibility, and expectations can make or break your first sales hire
👉 The importance of trust and alignment at the C-suite level for long-term go-to-market success

About our guest:
Eyal Worthalter, a multi-time cybersecurity sales leader, shares hard-won lessons from the frontline; including insights from his widely-read article on why most first VP of Sales hires fail. He’s contributed to Ross Haliliuk’s Venture In Security blog and works closely with founders and sales teams to help improve their approach to building go-to-market strategy.

Summary:
Listen in as Eyal Worthalter and Andrew Monaghan dig into the messy reality behind hiring the first sales leader, founder-led selling, investor pressure, and practical frameworks for scaling sales teams. If you want to avoid costly mistakes and build your sales org the right way, this episode will challenge your assumptions—don’t miss it!

Connect and Learn More:
Find Eyal Worthalter on LinkedIn. 

Ready to discuss your own sales challenges? Book time with Andrew Monaghan for a strategy session.

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