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

Jen Abel is GM of Enterprise at State Affairs and co-founded Jellyfish, a consultancy that helps founders learn zero-to-one enterprise sales. She’s one of the smartest people I’ve ever met on learning enterprise sales, and in this follow-up to our first chat two years ago (covering the zero to $1 million ARR founder-led sales phase), we focus on the skills founders need to learn to go from $1M to $10M ARR.

We discuss:

1. Why the “mid-market” doesn’t exist [04:38]

2. Why tier-one logos like Stripe and Tesla counterintuitively make the best early customers [08:08]

3. The dangers of pricing your product at $10K-$20K [15:35]

4. Why you need to vision-cast instead of problem-solve to win enterprise deals [10:50]

5. Why services are the fastest way to get your foot in the door with enterprises [36:55]

6. How to find and work with design partners [25:09]

7. When to hire your first salesperson and what profile to look for [50:24]

Also on Spotify and Apple Podcasts

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Where to find Jen Abel:

• X: https://x.com/jjen_abel

• LinkedIn: https://www.linkedin.com/in/earlystagesales

• Website: https://www.jjellyfish.com

Referenced:

• The ultimate guide to founder-led sales | Jen Abel (co-founder of JJELLYFISH): https://www.lennysnewsletter.com/p/master-founder-led-sales-jen-abel

• Mario meme: https://www.linkedin.com/pulse/missing-meme-led-me-woman-johann-van-tonder-im6df

• Kathy Sierra: https://en.wikipedia.org/wiki/Kathy_Sierra

• Cursor: https://cursor.com

• The rise of Cursor: The $300M ARR AI tool that engineers can’t stop using | Michael Truell (co-founder and CEO): https://www.lennysnewsletter.com/p/the-rise-of-cursor-michael-truell

• Justin Lawson on X: https://x.com/jjustin_lawson

• Stripe: https://stripe.com

• Building product at Stripe: craft, metrics, and customer obsession | Jeff Weinstein (Product lead): https://www.lennysnewsletter.com/p/building-product-at-stripe-jeff-weinstein

• He saved OpenAI, invented the “Like” button, and built Google Maps: Bret Taylor on the future of careers, coding, agents, and more: https://www.lennysnewsletter.com/p/he-saved-openai-bret-taylor

• OpenAI’s CPO on how AI changes must-have skills, moats, coding, startup playbooks, more | Kevin Weil (CPO at OpenAI, ex-Instagram, Twitter): https://www.lennysnewsletter.com/p/kevin-weil-open-ai

• Anthropic’s CPO on what comes next | Mike Krieger (co-founder of Instagram): https://www.lennysnewsletter.com/p/anthropics-cpo-heres-what-comes-next

• Linear: https://linear.app

• Linear’s secret to building beloved B2B products | Nan Yu (Head of Product): https://www.lennysnewsletter.com/p/linears-secret-to-building-beloved-b2b-products-nan-yu

• Gemini: https://gemini.google.com

• Microsoft Copilot: https://copilot.microsoft.com

• How Palantir built the ultimate founder factory | Nabeel S. Qureshi (founder, writer, ex-Palantir): https://www.lennysnewsletter.com/p/inside-palantir-nabeel-qureshi

• McKinsey & Company: https://www.mckinsey.com

• Deloitte: https://www.deloitte.com

• Accenture: https://www.accenture.com

• Building a world-class sales org | Jason Lemkin (SaaStr): https://www.lennysnewsletter.com/p/building-a-world-class-sales-org

• Peter Dedene on X: https://x.com/peterdedene

• Hang Huang on X: https://x.com/HH_HangHuang

• Hugo Alves on X: https://x.com/Ugo_alves

• A step-by-step guide to crafting a sales pitch that wins | April Dunford (author of Obviously Awesome and Sales Pitch): https://www.lennysnewsletter.com/p/a-step-by-step-guide-to-crafting

• Clay: https://www.clay.com

• Apollo: https://www.apollo.io

• Jason Lemkin on X: https://x.com/jasonlk

• Gavin Baker on X: https://x.com/GavinSBaker

• Jason Cohen on X: https://x.com/asmartbear

• Baywatch on Prime Video: https://www.primevideo.com/detail/Baywatch/0NU9YS8WWRNQO1NZD5DOQ3I8W6

• Playground: https://www.tryplayground.com

• ClassDojo: https://www.classdojo.com

• Jason Lemkin’s post about Replit: https://x.com/jasonlk/status/1946069562723897802

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Lenny may be an investor in the companies discussed.

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My biggest takeaways from this conversation: