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Lenny’s Podcast97 min

"Sell the alpha, not the feature": The enterprise sales playbook for $1M to $10M ARR

Jen Abel · Nov 9, 2025
Key learnings
  • Founder-led sales is a competitive advantage because founders are the visionary and can spot budding insights that salespeople…
  • Write cold outreach that leads with relevance, a counterintuitive insight, and the problem rather than the solution, kept to…
  • Before buying tools, manually find and write thoughtful notes to about 30 prospects; use the response pattern to refine messaging…
Lenny’s Podcast111 min

How to close $100K+ enterprise deals, step by step

Jen Abel · Aug 23, 2026
Key learnings
  • Target only the executive decision-maker or their direct report (N minus one) using a 'pincer' approach, with the founder…
  • Lead outreach with the executive-level value, the alpha your product unlocks for their career and business unit, not just…
  • Run the intro call as an informal one-on-one conversation: no demo, no slides, no recording, and let the buyer talk first to…