Lenny's Podcast · November 9, 2025

$1M to $10M: The enterprise sales playbook with Jen Abel

with Jen Abel 2.0

Learn the proven enterprise sales playbook that scales B2B startups from $1M to $10M ARR. Jen Abel reveals counterintuitive strategies for landing tier-one enterprise customers, including why to skip AI outbound tools for manual prospecting, how to price deals at $75K-150K from day one, and why selling services first creates the fastest path to enterprise adoption. Discover the art of deal crafting, ruthless qualification techniques, and how to hire enterprise salespeople who can cosplay as founders to vision-cast opportunities rather than solve problems.

Featured insight

Skip the AI outbound tools and go fully manual for enterprise sales. Everyone uses the same databases, so take the back door approach - find prospects not getting hit by a million automated emails and customize everything based on visual cues and timing. — Jen Abel

Best for: B2B SaaS founders scaling to enterprise, VP Sales at growth-stage startups, Enterprise sales leaders building playbooks

Loading the full episode…