CEOs Revealed: The Secret to Perfect Outbound Emails

In this concise monologue, Jason M. Lemkin explains why the most successful outbound emails get opened by CEOs of large companies and why most salespeople miss the mark. He notes that CEOs typically open any email that has a compelling headline, even though they receive thousands of messages, and they ignore generic, cadence‑driven or form‑letter emails. Lemkin criticizes the common salesmistake of relying on scripted cadences or bland outreach (e.g., “can I pick your brain?” or “buy me coffee?”). He stresses that the key to a perfect outbound email is reaching the right buyer at the right time with a headline that instantly signals relevance. He illustrates this with a personal anecdote: an early eSignature pitch, sent to the appropriate decision‑maker at the right moment, helped launch a company that later became worth $3 billion, even though the email itself was not elaborate. The overall message is that CEOs do open their emails when the content is targeted and compelling, and salespeople should abandon generic cadences in favor of highly personalized, timely outreach.










