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

Overview

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

Lenny's Podcast: Product | Career | Growth

Nov 09
Lenny's Podcast: Product | Career | Growth

Lenny's Podcast: Product | Career | Growth

Nov 09
OverviewShownoteHighlightsTranscriptChaptersPins

Shownote

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 ch...

Highlights

Scaling a startup from $1 million to $10 million in ARR demands more than just product-market fit—it requires a fundamental shift in sales strategy, positioning, and team building. In this deep dive, Jen Abel unpacks the nuanced realities of enterprise sales that founders often overlook when transitioning beyond early traction.
04:41
The mid-market doesn't exist in enterprise SaaS—it's either low-end enterprise or upper-end SMB.
08:08
Tier-one companies are willing to take risks for a slight edge
13:23
Sell the idea of customers becoming superheroes, not just solving problems
15:35
Large clients are more likely to be fully committed and help shape the product's future.
23:20
A 10x price increase requires delivering 15x the value to be defensible.
25:12
Converting a design partner to a full-rollout customer is a significant win
36:20
Most enterprises mention Gemini or Microsoft Copilot, not Anthropic.
39:50
Selling services first is a proven strategy to enter enterprise markets and later introduce scalable products.
43:21
Channel partnerships with consultancies like McKinsey aren't a viable strategy for startups
50:00
Say no as part of framing the partnership and setting expectations.
50:24
Salespeople should be able to 'cosplay a founder' to effectively sell the vision and adapt to enterprise clients.
59:36
Hire two salespeople at once because the failure rate is about 50%.
1:04:47
'No' is data—use it to move forward, not as a rejection.
1:07:31
A well-played deal can turn a hundred-thousand-dollar deal into a million-dollar one over time.
1:17:12
Be direct in communication and sales approach

Chapters

Welcome back, Jen!
00:00
The myth of the mid-market
04:38
Targeting tier-one logos
08:08
Vision-casting vs. problem-selling
10:50
The importance of high ACVs
15:35
 Don’t play the small business game with an enterprise company
20:45
Design partners: the double-edged sword
25:09
Finding the right company
28:11
Enterprise sales: the art of the deal
36:55
The problem with channel partnerships
43:21
Quick summary
44:41
Hiring the right enterprise salespeople
50:24
Structuring sales compensation
56:49
Building relationships in enterprise sales
1:01:01
The art of cold outreach
1:02:07
Outbound tooling and AI
1:07:31
Lightning round and final thoughts
1:14:08

Transcript

Jen Abel: you need to vision cast. You need to sell to a gap, don't sell to a problem. When you're selling to a leader, you need to be selling an opportunity. The market doesn't want to be sold to, they want to buy. Lenny Rachitsky: Most founders would ra...