Lenny's Podcast: Product | Career | Growth

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

1389 snips
Nov 9, 2025
Guest
Jen Abel
Jen Abel, a seasoned enterprise sales leader and co-founder of Jellyfish, shares her expertise on scaling B2B sales from $1M to $10M ARR. She debunks the myth of the mid-market, asserting that targeting tier-one logos yields strong references and roadmap influence. Abel highlights the importance of vision-casting instead of problem-solving to win enterprise deals and encourages founders to charge higher ACVs for better executive engagement. She also discusses strategic hiring, creative deal crafting, and the powerful role of tailored outreach in enterprise sales.
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00:00 / 00:00

Mid‑Market Is A False Middle

  • The "mid-market" is a myth because SMB and enterprise are fundamentally different games.
  • Mixing strategies for both leads to hiring and pricing mistakes that cause failure.
00:00 / 00:00

Go After Tier‑One Early

  • Pursue tier‑one logos early because they are incentivized to experiment and stay #1.
  • Use those logos as design partners to pull your roadmap and provide strong references.
00:00 / 00:00

Sell The Opportunity, Not The Problem

  • Vision‑cast to leaders: sell the opportunity and future state, not a narrow problem.
  • Anchor conversations on the upside that makes the buyer a 'superhero' to their org.
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