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Your First 10 Enterprise
Customers: The Manual

Jen Abel
Co-founder Jellyfish; formerly Enterprise Sales Director at The Muse and General Assembly
NOV 9 2025
The Truth

The Founder
Is the Product

FOUNDERINSIGHTMARKET
"Founder-led sales is not about revenue on day one. It is about learning as fast as humanly possible to get to that pulse, so that you can earn the right to sell."
  • In the very early days, before brand or references exist, the founder is the product
  • A lot of early-stage founders get tripped up taking late-stage sales advice
  • Only a founder can see the budding moments in a call, and that's where all the gold lives
  • Maybe you shouldn't hire any salespeople until Series A
The Sales Cycle

The Steps Most CRMs Are Set Up For

INTROSCOPEPROCUREMENT
6-12mo
typical enterprise deal cycle
  • Cold outreach has four parts: relevancy, counterintuitive angle, focus on the problem, concise (3-4 sentences max)
  • Relevancy matters more than personalization right now
  • Get the second call booked on the first call, pull up calendars
  • Please, please, please do not ask "what keeps you up at night?" That answer changes every single day
The vulnerability move"Hey, I'm an early-stage startup. We have a lot to learn. Can we gain your insight into how this problem is manifesting on your side?" If you say you're fully baked, you'll hamstring the intel you can gather.
What Kills Enterprise Deals

Where Deals Go Wrong

  • #1 Bad qualification: Everyone says they have a bottom-of-funnel problem. It's always a top-of-funnel problem
  • #2 Racing to demo upmarket: Once they see it, dreaminess is gone. Leave them wanting more
  • #3 Not knowing the signer: If the CFO doesn't know what they're signing, you drop to the bottom of their queue
  • #4 Procurement can't classify you: Then they hit you with the kitchen-sink MSA, a $5M insurance policy and access to your books
  • #5 Elongating calls: "Let's talk in two weeks." Two weeks? Do a week. Long gaps kill deals
Don't say "better"

A procurement lead once told Jen: the worst thing someone can say is "we're better than X." I ask them to define it, then how we'd measure it, then whether to give the incumbent another year. "Better" is a dangerous place.

The Gmail replay trick

Highlight your draft in Gmail and have it read back to you. "You'd be shocked how many notes I've changed when it replays it back and I'm like, oh, that sounds really passive-aggressive."

Playbook

How to Actually Start

  • Before you buy any tool, manually find 30 people you'd spend 15-20 minutes writing a rock-solid note to
  • If you can't even find 30, that's the signal, not a sales problem
  • 40-50% of B2B SaaS founders have to sell some form of service before they can sell the technology
  • Time-box services at 90 days, then rescope; don't lock yourself up longer
Trust is the currency"Trust is the number one currency in sales. If you are a trusted salesperson, people will recommend you all day and every day. If you're a trusted founder, your market will continually send you leads and word of mouth."
Contrarian

Enterprise Sales Myths

✗Hire a salesperson early to speed things upINSTEAD →✓ Maybe you shouldn't hire any salespeople until Series A. Seed is about experimentation; hiring for early-stage sales, the odds are more against you than the next round of funding.
✗Discount to get the deal over the lineINSTEAD →✓ You're negotiating with yourself. Only discount when they give something back: a design partner, a two-year reference. "If I give you a 30% discount, can I remove 30% of the value?"
✗Race to demo as fast as possibleINSTEAD →✓ Down-market yes. Upmarket, slow that demo down. Make sure the right people are in the room so it feels like the group's baby, not one lead's.
✗Founders should avoid services revenueINSTEAD →✓ 40-50% of B2B SaaS founders have to sell a service first. You get paid to educate them, you get the logo, and you set the mindset before the technology sale.
Based on Jen Abel's episode on Lenny's Podcast. All ideas on this page are from the episode.Watch on YouTubeFollow @jjen_abel on X
GO DEEPER IN THE EPISODE
04:38 The myth of the mid-market08:08 Targeting tier-one logos10:50 Vision-casting vs. problem-selling15:35 The importance of high ACVs20:45 Don’t play the small business game with an enterprise company25:09 Design partners: the double-edged sword28:11 Finding the right company36:55 Enterprise sales: the art of the deal43:21 The problem with channel partnerships44:41 Quick summary50:24 Hiring the right enterprise salespeople56:49 Structuring sales compensation01:01:01 Building relationships in enterprise sales01:02:07 The art of cold outreach01:07:31 Outbound tooling and AI01:14:08 Lightning round and final thoughts
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